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Vacation Rentals in Key West, Florida

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about Key West

Key West, Florida Vacation Rentals and Tourism

If you’re looking for the perfect summer beach house getaway, Key West should be your next destination. From bar hopping to island hopping, it doesn’t get much better than the tropical islands of the Keys, and thankfully, Key West vacation rentals welcome you with open arms.

Do you like to kayak? Fish? Scuba dive? Comb the beach? Swim with dolphins? Whatever the case, a Key West private beach rental is the best option for you and your fellow travelers, whether that includes just your significant other or several people. Sunny beaches, a thrilling nightlife, intriguing attractions like the Key West Museum of Art and History, Pirate Soul Museum, and Key West Aquarium, wonderful restaurants and bars, exciting boat tours, and much more await those who stay in a Key West beach cottage rental, condo, villa, or home.

It’s not an overstatement to say that your Key West summer beach house getaway will be remembered for as long as you live; you’ll want to come back to the tropical paradise again and again! Luckily, a Key West beach rental offers way more space and amenities than a hotel room, but at a much greater value. So with all your choices for Key West vacation rentals, you can easily have a priceless experience -- without going broke.

If you’re ready to experience one of the most relaxing and magical vacations of your lifetime, then find the Key West condo rental, home or villa that’s ideal for you and your price range.

Sights and tours to see:

Key West Museum of Art and History
Pirate Soul Museum
Key West Aquarium

Bars, people watching, beaches, sunsets: Key West is a great place to party and to relax! It's also a great place to score good deals on lodging with Key West discount vacation rentals. Whether you're going to party all night or go visit museums, we know you're the kind of person that likes to save money, and that's exactly what you'll do if you book one of our Key West vacation rental beach houses, condos or town homes. Key West vacation rentals are spacious, even luxurious, and all at an affordable price that will leave you and your budget more than satisfied. Key West vacation rental deals won't let you down.

 

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

Key West things to do

 

Key West Eco Tours Inc

Everything about this tour was fantastic. John, our guide, talked with the drawl of Matthew McConaughey and looked just like my friend Peter from college....read more

 

BluQ

We were on the Blu Q two concurrent days - we did an evening 4th of July cruise and a daytime snorkeling/sandbar cruise. Both were special experiences....read more

 

Dry Tortugas National Park

Camping here was the highlight of the past 10 years of my life. We (hubs and me) actually schlepped our kayaks all the way from Illinois down here and took...read more

 

Mallory Square

Mallory square is a cool place for souvenir shopping, and eats in Key West. They have all kinds of souvenirs here from cigars to sponges, and everything in...read more

 

Danger Charters

They should change there name to awesome charters! We had a blast. A great time on the water. The kayaking through the mangroves was my favorite part but...read more

 

Ernest Hemingway Home & Museum

So this was pretty cool! We were here about a week and a half ago and I opted out of the guided tour so we can do our own stuff. After reading some of the...read more

 

Sebago Water Sports

I went on the power adventure tour with my girlfriends during my bachelorette party this past weekend on 7/12/2014. We were amazed at how awesome the staff...read more

 

Green Parrot Bar

Second bar we went to in Key West on the recommendation of a bartender at the Rum Bar and ended up smack dab in the middle of the Russian Mafia! We...read more

 

Tropic Cinema

This theatre was definitely fun to visit! The theater was very small and intimate and the theme is very old Hollywood and it's beautiful. Staff was friendly...read more

 

Dive Key West Inc

Very disappointed with their customer service and how they speak to customers. We will never be using them again. Worst experience on our whole trip.read more

 

Floridays

My wife and I booked a snorkeling trip nearly 5 weeks ago. We wanted a smaller group and were willing to pay extra as compared to the larger tour...read more

 

Wyland Gallery of Key West

Beautiful Artwork and Excellent staff. Great place to get inspired, refreshed and educated.read more

 

Fury Water Adventures

Tickets; My wife and I purchased Fury's Parasailing tickets at the ITT office (military discount) at Sigbee Navy Station for $30 each. We decided to go on...read more

 

Little Room Jazz Club

Super nice bar with excellent service. My wife and I stopped in around 3pm to cool down from the blistering heat. We sat at the bar and were greeted by the...read more

 

Barefoot Billy's

My friend and I were in Key West for the day and decided to go parasailing. First and foremost, Barefoot Billy's prices are amazing. We were staying in Ft....read more

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DEAL!! Emma House & Cottage Plus Pvt. Pool
Key West House Rental Picture
  • House Rental Deals and Discounts $500 off = $2,850 per week
  • House Rental Deals and Specials Housekeeping ($150)
  • bedrooms 3
  • community Truman Annex
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $2,650 - $5,500 /wk
    $9,000 - $17,500 /mth
 
 
 
 
 

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DEAL!! A Touch of Bermuda in Key West
Key West Cottage Rental Picture
  • Cottage Rental Deals and Discounts $350 off = $1,400 per week
  • Cottage Rental Deals and Specials Family pass to Ft. Zach beach ($150)
  • bedrooms 2
  • community Truman Annex
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,750 - $2,200 /wk
    $5,250 - $6,900 /mth
 
 
 
 
 

8 reviews write a review

DEAL!! Baya House - a great old town location
Key West Townhome Rental Picture
  • Townhome Rental Deals and Discounts 25% off = $1,125 per week
  • bedrooms 2
  • community Windward Park
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,300 - $2,700 /wk
    $5,000 - $6,700 /mth
 
 
 
 
 

13 reviews write a review

DEAL!! 1 Blk fron Duval! - Historic Eyebrow Home Old Town Key West
Key West House Rental Picture
  • House Rental Deals and Discounts $800 off = $2,790 per week
  • bedrooms 4
  • community Old Town
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 4
  • rates (USD) $2,890 - $4,990 /wk
 
 
 
 
 

4 reviews write a review

DEAL!! Key West Harbour Oceanfront Suites
Key West Condo Rental Picture
  • Condo Rental Deals and Discounts free night valued at USD $229
  • bedrooms 2
  • community Stock Island
  • rental type Condo
  • sleeps 4
  • baths
  • rates (USD) $229 - $489 /nt
    $1,603 - $3,423 /wk
    $8,000 - $14,000 /mth
 
 
 
 
 

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Attitude Key West includes 2 Bikes and WiFi
Key West Condo Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,150 - $2,500 /wk
    $4,500 - $6,660 /mth
 
 
 
 
 

22 reviews write a review

Steps to Duval! La Dolce Vita, luxury, sleeps 2-4
Key West Condo Rental Picture
  • bedrooms 1
  • community Old Town
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $198 - $278 /nt
    $1,250 - $1,800 /wk
 
 
 
 
 

37 reviews write a review

Key West's Truman Annex Sunset & Ocean View, Two Bicycles
Key West Condo Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,400 - $2,050 /wk
    $6,600 - $7,000 /mth
 
 
 
 
 

66 reviews write a review

Henry's Penthouse On the Ocean In Key West - Weekly Rental
Key West Condo Rental Picture
  • bedrooms 2
  • community 1800 Atlantic
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,750 - $2,700 /wk
 
 
 
 
 

16 reviews write a review

Henry s Piece Of Paradise On The Ocean In Key West
Key West Condo Rental Picture
  • bedrooms 2
  • community 1800 Atlantic
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $245 - $405 /nt
    $1,550 - $2,600 /wk
 
 
 
 
 

16 reviews write a review

Attitude Key West At the Beach 2 bikes and WiFi
Key West Condo Rental Picture
  • bedrooms 1
  • community 1800 Atlantic
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $190 - $300 /nt
    $1,050 - $2,500 /wk
    $4,500 - $7,020 /mth
 
 
 
 
 

23 reviews write a review

"Bella Vita"
Key West Condo Rental Picture
  • bedrooms 1
  • community Old Town
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $198 - $278 /nt
    $1,250 - $1,800 /wk
 
 
 
 
 

36 reviews write a review

Key West Beachfront Luxury 2/2 Condo A212
Key West Condo Rental Picture
  • bedrooms 2
  • community 1800 Atlantic
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $295 - $400 /nt
    $1,859 - $2,457 /wk
    $4,100 - $7,000 /mth
 
 
 
 
 

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Tee By The Sea
Key West Townhome Rental Picture
  • bedrooms 2
  • community Coral Hammock
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $250 - $450 /nt
    $1,300 - $2,200 /wk
    $5,200 - $7,200 /mth
 
 
 
 
 

39 reviews write a review

!!!Steps from Duval $89-$139 Night - Free Bikes Included!!!
Key West Studio Rental Picture
  • bedrooms 0
  • community
  • rental type Studio
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $89 - $139 /nt
    $623 - $973 /wk
 
 
 
 
 

35 reviews write a review

Luxury and Spacious Condo on Duval Steet
Key West Condo Rental Picture
  • bedrooms 2
  • community Cuban Club Suites
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $330 - $525 /nt
    $1,855 - $3,325 /wk
    $6,625 - $7,925 /mth
 
 
 
 
 

42 reviews write a review

Your condo by the BEACH with OCEAN view
Key West Condo Rental Picture
  • bedrooms 1
  • community La Brisa Condos
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,015 - $1,600 /wk
 
 
 
 
 

18 reviews write a review

Ocean Vista
Key West Condo Rental Picture
  • bedrooms 2
  • community La Brisa Condos
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $250 - $325 /nt
    $1,575 - $2,100 /wk
    $3,000 - $4,500 /mth
 
 
 
 
 

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Simonton Studio, an Old Town get-away for 2
Key West Studio Rental Picture
  • bedrooms 0
  • community Old Town
  • rental type Studio
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $130 - $230 /nt
    $850 - $1,600 /wk
 
 
 
 
 

32 reviews write a review

Mermaid's Dream
Key West Townhome Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,800 - $2,300 /wk
    $6,700 - $8,500 /mth
 
 
 
 
 

5 reviews write a review

Fabulous New Houseboat! Sleeps 8!
Key West Houseboat Rental Picture
  • bedrooms 3
  • community
  • rental type Houseboat
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $300 - $500 /nt
    $2,100 - $3,100 /wk
 
 
 
 
 

18 reviews write a review

One of a Kind Condo at the Galleon Resort & Marina
Key West Condo Rental Picture
  • bedrooms 1
  • community Galleon Resort
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $350 - $480 /nt
    $2,125 - $3,300 /wk
 
 
 
 
 

10 reviews write a review

Waterfront 2/2 Penthouse Loft in Old Town
Key West Condo Rental Picture
  • bedrooms 2
  • community Galleon Resort
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $450 - $625 /nt
    $2,750 - $4,150 /wk
 
 
 
 
 

8 reviews write a review

Easy Livin' - Truman Annex Villa
Key West Villa Rental Picture
  • bedrooms 3
  • community Truman Annex
  • rental type Villa
  • sleeps 8
  • baths 4
  • rates (USD) $4,000 - $8,700 /wk
 
 
 
 
 

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The Victoria House - Wonderful 5 bed Villa
Key West House Rental Picture
  • bedrooms 5
  • community Old Town
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $865 - $1,225 /nt
    $5,800 - $8,300 /wk
 
 
 
 
 

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Amelia Home- Private Pool, Old Town Key West
Key West House Rental Picture
  • bedrooms 2
  • community Old Town
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $2,100 - $3,600 /wk
 
 
 
 
 

1 reviews write a review

Bahama Dreaming - Great Old Town Location
Key West House Rental Picture
  • bedrooms 3
  • community Old Town
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $2,925 - $4,980 /wk
 
 
 
 
 

2 reviews write a review

Duval Sea Turtle 2 Bed/2.5 Bath Duval Square
Key West Condo Rental Picture
  • bedrooms 2
  • community Duval Square
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $225 - $360 /nt
    $1,350 - $2,370 /wk
 
 
 
 
 

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Sunshine Luxury Suite - 2 Free Bikes & Garage
Key West Condo Rental Picture
  • bedrooms 2
  • community Sunrise
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,300 - $2,000 /wk
    $4,500 - $6,500 /mth
 
 
 
 
 

31 reviews write a review

Old Town Condo near Beach
Key West Condo Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,200 - $2,100 /wk
 
 
 
 
 

10 reviews write a review

Galleon Resort at Affordable Rates
Key West Studio Rental Picture
  • bedrooms 0
  • community Galleon Resort
  • rental type Studio
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $185 - $265 /nt
    $1,100 - $1,750 /wk
 
 
 
 
 

8 reviews write a review

Southernmost Retreat
Key West House Rental Picture
  • bedrooms 3
  • community Simonton Cottages
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $238 - $408 /nt
    $1,666 - $2,856 /wk
 
 
 
 
 

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Tropical Paradise on the Atlantic Ocean
Key West Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $300 - $320 /nt
    $2,100 - $2,170 /wk
 
 
 
 
 

3 reviews write a review

Dos Casas -Beautiful Two House Compound in Old Town Key West
Key West House Rental Picture
  • bedrooms 4
  • community Old Town
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $5,500 - $9,500 /mth
 
 
 
 
 

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Key West's Truman Annex Poolside & Ocean Peek with 2 Bikes
Key West Condo Rental Picture
  • bedrooms 1
  • community Truman Annex
  • rental type Condo
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $1,300 - $2,700 /wk
    $4,400 - $6,600 /mth
 
 
 
 
 

45 reviews write a review

Seaside Place 5 Bedroom Old Town Key West Florida
Key West House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 4
  • rates (USD) $700 - $1,000 /nt
    $4,900 - $7,000 /wk
 
 
 
 
 

10 reviews write a review

Prime location! Rare 2BR, 2B in Truman Annex
Key West Condo Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,400 - $2,400 /wk
    $3,629 - $8,571 /mth
 
 
 
 
 

30 reviews write a review

Island Wind Old Town Tropical Hideaway
Key West Townhome Rental Picture
  • bedrooms 2
  • community Windward Park
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,390 - $2,500 /wk
 
 
 
 
 

5 reviews write a review

Harbor Walk Hideaweays
Key West Villa Rental Picture
  • bedrooms 4
  • community Old Town
  • rental type Villa
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $260 - $625 /nt
    $2,200 - $4,975 /wk
 
 
 
 
 

4 reviews write a review

Castaway Duval street Townhome
Key West Townhome Rental Picture
  • bedrooms 2
  • community Duval Square
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $1,350 - $1,950 /wk
 
 
 
 
 

2 reviews write a review

Old Town Luxury Oasis
Key West House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $3,000 - $6,500 /mth
 
 
 
 
 

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Tropical Breezes on Duval St ( fomerly 26428)
Key West Townhome Rental Picture
  • bedrooms 2
  • community Duval Square
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $4,000 - $6,000 /mth
 
 
 
 
 

1 reviews write a review

La Brisa Beachfront Condo
Key West Condo Rental Picture
  • bedrooms 2
  • community La Brisa Condos
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $250 - $425 /nt
    $1,800 - $2,800 /wk
 
 
 
 
 

13 reviews write a review

Key West is Rockin, Golf Club Condo
Key West Condo Rental Picture
  • bedrooms 2
  • community Key West Golf Club
  • rental type Condo
  • sleeps 4
  • baths
  • rates (USD) $2,500 - $3,500 /mth
 
 
 
 
 

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Blue Lagoon
Key West Townhome Rental Picture
  • bedrooms 3
  • community Truman Annex
  • rental type Townhome
  • sleeps 6
  • baths 2
  • rates (USD) $2,500 - $3,500 /wk
 
 
 
 
 

1 reviews write a review

Designer Dream Luxury Home
Key West House Rental Picture
  • bedrooms 3
  • community neighbourhood
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $5,000 - $8,000 /mth
 
 
 
 
 

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Shipyard Tropical Retreat
Key West Townhome Rental Picture
  • bedrooms 2
  • community Shipyard
  • rental type Townhome
  • sleeps 4
  • baths 1
  • rates (USD) $3,000 - $5,500 /mth
 
 
 
 
 

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Key West Vacation Rental
Key West House Rental Picture
  • bedrooms 1
  • community
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $3,000 /mth
 
 
 
 
 

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A Very Special Conch House
Key West House Rental Picture
  • bedrooms 2
  • community Old Town
  • rental type House
  • sleeps 4
  • baths
  • rates (USD) $4,000 - $6,400 /mth
 
 
 
 
 

1 reviews write a review

Painter's Paradise
Key West House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 4
  • baths
  • rates (USD) $2,200 - $3,900 /mth
 
 
 
 
 

1 reviews write a review

Island Retreat
Key West House Rental Picture
  • bedrooms 2
  • community Windward Park
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,575 - $2,900 /wk
 
 
 
 
 

4 reviews write a review

Truman At Duval
Key West Apartment Rental Picture
  • bedrooms 2
  • community
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $228 /nt
    $1,246 - $1,596 /wk
 
 
 
 
 

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Havana Hideaway, Private Pool & Parking, Just off Duval St.
Key West House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $398 - $498 /nt
 
 
 
 
 

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YACHT Dolphin Lady 3bed/3bath
Key West Houseboat Rental Picture
  • bedrooms 3
  • community Oceanside Marina
  • rental type Houseboat
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $185 - $186 /nt
    $1,295 - $1,296 /wk
    $5,180 - $5,190 /mth
 
 
 
 
 

5 reviews write a review

Truman Annex Shipyard with Tropical Garden
Key West Villa Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Villa
  • sleeps 4
  • baths 1
  • rates (USD) $850 - $1,800 /wk
 
 
 
 
 

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Galleon Resort
Key West Condo Rental Picture
  • bedrooms 2
  • community Galleon Resort
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,500 /wk
 
 
 
 
 

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Ivory Coast
Key West Townhome Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $1,600 - $2,800 /wk
 
 
 
 
 

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Tropical Retreat
Key West Cottage Rental Picture
  • bedrooms 2
  • community
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $198 - $258 /nt
    $1,386 - $1,806 /wk
 
 
 
 
 

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Southern Cross
Key West House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $258 - $308 /nt
    $1,806 - $2,156 /wk
 
 
 
 
 

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Poolside Paradise
Key West Cottage Rental Picture
  • bedrooms 1
  • community
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $168 /nt
    $1,176 /wk
 
 
 
 
 

1 reviews write a review

Absolutely Paradise
Key West House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $408 - $508 /nt
    $2,856 - $3,556 /wk
 
 
 
 
 

2 reviews write a review

Seaport Suite, 1 Block off Duval Street, Walk Everywhere!
Key West House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $348 - $448 /nt
    $2,436 - $3,136 /wk
 
 
 
 
 

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Pet Friendly Cottage
Key West Studio Rental Picture
  • bedrooms 0
  • community
  • rental type Studio
  • sleeps 4
  • baths 1
  • rates (USD) $128 - $148 /nt
    $896 - $1,036 /wk
 
 
 
 
 

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Palm Isle, Adorable Treetop Unit, 1 Block off Duval Street
Key West Studio Rental Picture
  • bedrooms 0
  • community
  • rental type Studio
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $168 - $248 /nt
    $1,176 - $1,736 /wk
 
 
 
 
 

3 reviews write a review

Little Palm - Absolute Dream Cottage w/Private Hot Tub +
Key West Studio Rental Picture
  • bedrooms 0
  • community
  • rental type Studio
  • sleeps 2
  • baths 1
  • rates (USD) $198 - $268 /nt
 
 
 
 
 

5 reviews write a review

Island Oasis, Private Pool, 1 Block off Duval Street
Key West House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $368 - $468 /nt
    $2,576 - $3,276 /wk
 
 
 
 
 

4 reviews write a review

Key West Hidaway
Key West House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $5,000 - $7,500 /mth
 
 
 
 
 

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Tropical Hideaway
Key West Cottage Rental Picture
  • bedrooms 1
  • community
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $198 - $278 /nt
    $1,386 - $1,946 /wk
 
 
 
 
 

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Key West Cottage: Bahama House, Key West, FL, 33040
Key West Cottage Rental Picture
  • bedrooms 2
  • community
  • rental type Cottage
  • sleeps 6
  • baths 2
  • rates (USD) $298 - $388 /nt
    $2,086 - $2,716 /wk
 
 
 
 
 

1 reviews write a review

Toon Hall
Key West House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $348 - $448 /nt
    $2,436 - $3,136 /wk
 
 
 
 
 

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Tropical Village Cottage
Key West Cottage Rental Picture
  • bedrooms 2
  • community
  • rental type Cottage
  • sleeps 5
  • baths 2
  • rates (USD) $245 - $295 /nt
    $1,715 - $2,065 /wk
 
 
 
 
 

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Villa Al Mar
Key West House Rental Picture
  • bedrooms 6
  • community
  • rental type House
  • sleeps 13
  • baths 6
  • rates (USD) $10,000 - $12,000 /wk
    $28,000 - $32,000 /mth
 
 
 
 
 

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Old Town Truman & Duval Condo
Key West Townhome Rental Picture
  • bedrooms 2
  • community Windward Park
  • rental type Townhome
  • sleeps 4
  • baths 2
  • rates (USD) $265 - $325 /nt
    $1,575 - $2,000 /wk
 
 
 
 
 

1 reviews write a review

Voted Nicest Rental Home in Lower Keys !!
Key West House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $12,500 - $14,500 /mth
 
 
 
 
 

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Key West's only real Beach House,private,gated,tropical
Key West House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $2,400 - $4,800 /wk
 
 
 
 
 

1 reviews write a review

A Paradise Vacation
Key West Condo Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $900 - $1,800 /wk
    $3,600 - $5,400 /mth
 
 
 
 
 

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- Delightful Deluxe Condo----July-Sept special
Key West Condo Rental Picture
  • bedrooms 1
  • community
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $2,400 - $6,400 /mth
 
 
 
 
 

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Key West's only Real Beach House,private,tropical,gated
Key West House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $2,400 - $3,750 /wk
 
 
 
 
 

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Casa VonPhister
Key West House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $6,000 - $10,000 /mth
 
 
 
 
 

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Luxurious, Elegant, Quiet
Key West House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $3,500 - $4,200 /wk
    $12,000 /mth
 
 
 
 
 

1 reviews write a review

Coral Hammock - Beautiful Home at the entrance to Key West (35)
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $225 - $300 /nt
    $1,000 - $1,600 /wk
 
 
 
 
 

7 reviews write a review

~$~1,300/wk - Best Deal in Key West - Plus 7 Bikes Included!
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $250 - $500 /nt
    $1,302 - $2,205 /wk
 
 
 
 
 

39 reviews write a review

'Amberjack' A Little Slice of Key West Heaven
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

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Tiki Beach Too, Charming Townhome, OldTown, Pool Access, Budget, Hideaway Porch!
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $1,346 - $1,946 /wk
    $2,995 - $4,865 /mth
 
 
 
 
 

9 reviews write a review

:: OLD TOWN OASIS @ THE ANNEX :: Lavish & Airy / Oceanfront Pool / Near Duval...
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $3,000 - $4,000 /wk
    $7,700 - $14,500 /mth
 
 
 
 
 

49 reviews write a review

:: CASA, SUITE CASA @ CASA MARINA :: Lush New Home / 4 BR Suites / Pool & Spa...
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 5
  • rates (USD) $9,000 - $20,000 /mth
 
 
 
 
 

4 reviews write a review

:: WINDSWEPT PALMS @ THE BEACH :: Fabulous Oceanfront / Large Pool & Jacuzzi....
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $550 - $890 /nt
    $2,750 - $4,900 /wk
    $10,000 - $16,000 /mth
 
 
 
 
 

2 reviews write a review

:: NANCY'S SEASIDE RETREAT @ FLORIDA BAY :: Waterfront & Pool / Roomy & Airy....
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $6,000 - $12,500 /mth
 
 
 
 
 

1 reviews write a review

:: AZURE AFTERNOON @ OCEANSIDE MARINA :: Oceanfront / By Marina / Pool & Spa....
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $2,100 - $3,200 /wk
    $7,500 - $11,750 /mth
 
 
 
 
 

17 reviews write a review

:: SUZY'S PARROT PERCH @ SOUTHERNMOST :: Cozy 2nd Floor Suite / Block to Duval..
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $290 - $450 /nt
    $1,450 - $2,350 /wk
    $4,900 - $8,250 /mth
 
 
 
 
 

28 reviews write a review

:: THE CAPTAIN'S ANNEX @ PARADISE HARBOR :: Gorgeous Home / Pool & Boat Slip....
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $675 - $1,025 /nt
    $4,200 - $6,200 /wk
    $14,000 - $21,000 /mth
 
 
 
 
 

24 reviews write a review

:: PUERTA CORALINA @ SOLARES HILL :: Cozy Conch Cottage & Pool / Near Duval.....
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $390 - $750 /nt
    $2,150 - $3,950 /wk
    $6,600 - $14,000 /mth
 
 
 
 
 

58 reviews write a review

:: COMMODORE'S MANOR @ PARADISE HARBOR :: Grand Waterfront Home / Pool & Dock...
Key West Townhome Rental Picture
  • bedrooms 5
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 14
  • baths 4
  • rates (USD) $1,250 - $1,800 /nt
    $6,950 - $10,000 /wk
    $20,000 - $33,000 /mth
 
 
 
 
 

50 reviews write a review

Truman Annex - 1BR/1BA - Renovated Corner Unit wtih GREAT REVIEWS!!!!
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

23 reviews write a review

Truman Annex Best Location in Town
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $1,600 - $2,200 /wk
    $4,800 - $7,920 /mth
 
 
 
 
 

8 reviews write a review

Coral Hammock - Tropical Paradise Home (15)
Key West Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $250 - $375 /nt
    $1,200 - $2,100 /wk
    $5,500 - $7,500 /mth
 
 
 
 
 

5 reviews write a review

Watch the sunset from the Infinity pool
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,751 /wk
 
 
 
 
 

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Spa On Duval: 2 BR / 2.5 BA 2 bedroom condo in Key West, Sleeps 6
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $240 - $479 /nt
    $1,450 - $3,275 /wk
 
 
 
 
 

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:: NATALIE'S BAHAMA CONCH @ THE SANCTUARY :: Luxurious / Gated / Private Pool...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $5,000 - $9,550 /mth
 
 
 
 
 

4 reviews write a review

Duval St. Luxury Penthouse (Private Pool, Parking, Roof Deck)
Key West Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD)
 
 
 
 
 

4 reviews write a review

:: FLAMINGO DREAMS @ SOLARES HILL :: Pristine Conch Home & Pool / Near Duval...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $5,700 - $15,000 /mth
 
 
 
 
 

6 reviews write a review

"OCEANIA SUITE" - Quiet 'Old Town' Cottage - Beautiful Shared Pool
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $258 /nt
    $1,246 - $2,226 /wk
    $5,340 - $7,740 /mth
 
 
 
 
 

15 reviews write a review

"BERMUDA SUITE" - 2-Story Home w/ Shared Pool 1/2 Block To Duval St!
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • sleeps 4
  • baths
  • rates (USD) $188 - $268 /nt
    $1,316 - $2,296 /wk
    $5,640 - $8,040 /mth
 
 
 
 
 

15 reviews write a review

"ALMOST SOUTHERNMOST TOO" - Private Pool - Half Block To Duval St!
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $378 - $618 /nt
    $2,646 - $4,676 /wk
    $11,340 - $18,540 /mth
 
 
 
 
 

10 reviews write a review

ALMOST SOUTHERNMOST RETREAT Pvt Pool & Hot Tub -1/2 Block to Duval -Sleeps 14
Key West House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 16
  • baths
  • rates (USD) $638 - $868 /nt
    $4,466 - $8,736 /wk
    $19,140 - $26,040 /mth
 
 
 
 
 

4 reviews write a review

''ABACO SUITE'' - Beautiful 2-Story Home in Amazing Location w/ Shared Pool
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $258 /nt
    $1,246 - $2,226 /wk
    $5,340 - $7,740 /mth
 
 
 
 
 

12 reviews write a review

"FOR WHOM THE BELL TOLLS" - Papas Hideaway's Deluxe Studio 3, Shared Pool
Key West Apartment Rental Picture
  • bedrooms 0
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD) $188 - $238 /nt
    $1,316 - $2,366 /wk
    $5,640 - $7,140 /mth
 
 
 
 
 

12 reviews write a review

A Place in Paradise: 2 BR / 2.5 BA 2 bedroom condo in Key West, Sleeps 6
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $1,550 - $3,444 /wk
 
 
 
 
 

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Beach Club #104 - Unique oceanfront living with breathtaking views
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $290 - $420 /nt
    $1,890 - $3,500 /wk
 
 
 
 
 

9 reviews write a review

Catherine House: A charming Old Town Key West cottage
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $290 - $420 /nt
    $1,890 - $3,220 /wk
 
 
 
 
 

35 reviews write a review

"SOUTHERNMOST RETREAT" - Big Condo w/ Shared Hot Tub Located On Duval St!
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $228 - $338 /nt
    $1,596 - $3,066 /wk
    $6,840 - $10,140 /mth
 
 
 
 
 

16 reviews write a review

ORCHID SUITE - 1 Bd, 1 Bth, 1 Block From Duval - Private Parking!
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $148 - $218 /nt
    $1,036 - $1,946 /wk
    $4,440 - $6,540 /mth
 
 
 
 
 

7 reviews write a review

"BOARDWALK LOFT" - Monthly Rental - Newly Renovated Condo w/ Shared Pool.
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $2,800 - $5,089 /mth
 
 
 
 
 

2 reviews write a review

Key West Vacation Rental 'Southard Comfort' Historic Old Town Private Pool
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $490 - $828 /nt
    $5,796 /wk
 
 
 
 
 

16 reviews write a review

"HAVANA OASIS" Luxury 2-Home, Group Rental w/ 2 Pvt Pools. Sleeps 12!
Key West Townhome Rental Picture
  • bedrooms 4
  • rental type Townhome
  • sleeps 12
  • baths 5
  • rates (USD) $648 - $848 /nt
    $4,536 - $7,196 /wk
    $19,440 - $25,440 /mth
 
 
 
 
 

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:: FOLLOW THE SUN @ THE BEACH :: Ocean View / Large Pool & Jacuzzi / Tennis.....
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $332 - $707 /nt
    $1,853 - $4,949 /wk
    $5,995 - $10,791 /mth
 
 
 
 
 

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:: BAHAMIAN BAMBOO @ THE ANNEX :: Bright & Breezy / Pool / Near Duval & Beach...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $628 - $1,415 /nt
    $4,404 - $9,908 /wk
    $17,985 - $25,016 /mth
 
 
 
 
 

2 reviews write a review

:: THE LILAC COTTAGE @ SOLARES HILL :: Charming Cottage & Pool / Near Duval.....
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $4,502 - $11,500 /mth
 
 
 
 
 

2 reviews write a review

Rent a Piece of Paradise!
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $200 - $300 /nt
    $1,200 - $1,900 /wk
 
 
 
 
 

8 reviews write a review

The Red Grouper - A Funky Floating Condo with Direct Ocean Access
Key West House_boat Rental Picture
  • bedrooms 1
  • rental type House boat
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $165 - $240 /nt
    $1,000 - $1,450 /wk
 
 
 
 
 

15 reviews write a review

Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,400 - $2,050 /wk
    $4,800 - $7,000 /mth
 
 
 
 
 

66 reviews write a review

Key West vacation townhouse rental in the Truman Annex
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,400 - $3,300 /wk
    $5,500 /mth
 
 
 
 
 

5 reviews write a review

"SEASIDE HIDEAWAY" Beautiful Key West Condo w/ Shared Pool & Tennis Courts
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,500 - $5,893 /mth
 
 
 
 
 

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"DUVAL DELIGHT" Gorgeous New Condo On Duval Street! Sleeps 6! Pvt Parking!
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $218 - $348 /nt
    $1,806 - $3,136 /wk
    $7,740 - $10,440 /mth
 
 
 
 
 

2 reviews write a review

"SIMONTON COURT COTTAGES" 4 Units in 1! Sleeps up to 10 Only 1 Block To Duval
Key West Cottage Rental Picture
  • bedrooms 4
  • rental type Cottage
  • sleeps 10
  • baths 5
  • rates (USD) $548 - $798 /nt
    $3,836 - $7,056 /wk
    $16,440 - $23,940 /mth
 
 
 
 
 

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Key West ocean view 3 bedroom Truman Annex vacation condo
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $3,300 - $6,000 /wk
    $11,000 - $17,000 /mth
 
 
 
 
 

3 reviews write a review

"SUNSET SUITE" Romantic Getaway for 2 - Private Hot Tub - 1/2 Block To Duval
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $208 - $288 /nt
    $1,456 - $2,436 /wk
    $6,240 - $8,640 /mth
 
 
 
 
 

8 reviews write a review

"MONROE EFFICIENCY - NIGHTLY" - A Block From Duval St. 'Night Life'
Key West Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $138 - $208 /nt
    $966 - $1,876 /wk
    $4,140 - $6,240 /mth
 
 
 
 
 

12 reviews write a review

"HONEYMOON HIDEAWAY" Romantic Getaway Spot For Two - Private Hot Tub
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $178 - $258 /nt
    $1,246 - $2,226 /wk
    $5,340 - $7,740 /mth
 
 
 
 
 

17 reviews write a review

."CASA GRANDE" Over 3400 Sq Ft of Luxury Home in Old Town's 'Heart'
Key West House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 14
  • baths
  • rates (USD) $768 - $1,148 /nt
    $5,376 - $9,786 /wk
    $23,040 - $34,440 /mth
 
 
 
 
 

8 reviews write a review

'Casa Coral' Relaxing Key West Townhome In Gated Community, Sleeps 6
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $240 - $432 /nt
    $1,480 - $2,824 /wk
 
 
 
 
 

24 reviews write a review

'Casa Caribe' Tropical Key West Townhome in Gated Community, Sleeps 6
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $240 - $432 /nt
    $1,480 - $2,824 /wk
 
 
 
 
 

9 reviews write a review

THE COTTAGE @ TROPICAL VILLAGE - Spacious Home w/ Shared Pool. Close To Beach
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 6
  • baths 2
  • rates (USD) $268 - $368 /nt
    $1,876 - $3,136 /wk
    $8,040 - $11,040 /mth
 
 
 
 
 

4 reviews write a review

"CASA DE MANGO @ DUVAL SQUARE" 2-Story Condo w/ Pvt Hot Tub & Balcony
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $268 - $368 /nt
    $1,876 - $3,206 /wk
    $8,040 - $11,040 /mth
 
 
 
 
 

12 reviews write a review

Mango Menagerie: A treasury of island colors and Key West charm
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $3,200 - $4,000 /mth
 
 
 
 
 

2 reviews write a review

Shipyard Palms: A first floor condo in the Shipyard of Truman Annex
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $1,610 - $2,450 /wk
    $4,200 - $4,500 /mth
 
 
 
 
 

12 reviews write a review

Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E)
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $200 - $330 /nt
    $1,330 - $2,590 /wk
 
 
 
 
 

23 reviews write a review

Sunshine, beaches, and ocean breezes at Ocean Vista (La Brisa #403E)
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $180 - $330 /nt
    $1,190 - $2,590 /wk
 
 
 
 
 

19 reviews write a review

Enjoy soothing ocean breezes at Tropical Tranquility (La Brisa #302E)
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $170 - $240 /nt
    $1,120 - $2,240 /wk
 
 
 
 
 

14 reviews write a review

Duval Square Courtyard Condo is just steps from the action
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $310 - $430 /nt
    $2,030 - $3,430 /wk
 
 
 
 
 

15 reviews write a review

Duval Square Retreat: A beautiful condo steps from the action
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $250 - $350 /nt
    $1,680 - $3,010 /wk
 
 
 
 
 

14 reviews write a review

Casa Atlantica: A studio condo on the Atlantic shore of Key West
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $160 - $240 /nt
    $1,050 - $1,750 /wk
 
 
 
 
 

25 reviews write a review

Beach Club #204 - Unique Oceanfront living
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $290 - $420 /nt
    $1,890 - $3,500 /wk
 
 
 
 
 

12 reviews write a review

Louisa House: A comfortable four bedroom vacation hideaway
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $470 - $690 /nt
    $3,150 - $5,600 /wk
 
 
 
 
 

27 reviews write a review

Pete's West Cottage steps from Duval
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $260 - $370 /nt
    $1,680 - $2,940 /wk
 
 
 
 
 

10 reviews write a review

Pete's Cottages: Twin Cypress cottages steps from Duval
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $450 - $660 /nt
    $3,010 - $5,460 /wk
 
 
 
 
 

16 reviews write a review

Key Lime Calypso: A cottage in the heart of Bahama Village
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $270 - $350 /nt
    $1,820 - $2,800 /wk
 
 
 
 
 

19 reviews write a review

Ann Street Cottage: A bright and airy home near Duval Street
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 2
  • baths
  • rates (USD) $220 - $320 /nt
    $1,470 - $2,380 /wk
 
 
 
 
 

17 reviews write a review

Havana Lane: A classic conch cottage with rustic charm
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $320 - $430 /nt
    $2,030 - $3,500 /wk
 
 
 
 
 

13 reviews write a review

Newton Street Hideaway: A secluded one bedroom
Key West House Rental Picture
  • bedrooms 1
  • rental type House
  • sleeps 2
  • baths 2
  • rates (USD) $3,200 - $4,000 /mth
 
 
 
 
 

1 reviews write a review

Angela Cottage: A hideaway in Old Town
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $3,500 - $5,000 /mth
 
 
 
 
 

5 reviews write a review

Idyllic courtyard and location
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 6
  • baths 1
  • rates (USD) $228 - $418 /nt
 
 
 
 
 

1 reviews write a review

ESCAPE 2 PARADISE - 2 Beautiful 3-Story Homes w/ Pvt Pools. Steps From Duval
Key West Townhome Rental Picture
  • bedrooms 6
  • rental type Townhome
  • sleeps 16
  • baths 5
  • rates (USD) $738 - $1,118 /nt
    $5,166 - $9,716 /wk
    $22,140 - $33,540 /mth
 
 
 
 
 

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"Hibiscus Efficiency" - Private Parking - Perfect Location
Key West Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $128 - $198 /nt
    $896 - $1,806 /wk
    $3,840 - $5,940 /mth
 
 
 
 
 

9 reviews write a review

'POTTER`S COTTAGE' Historic Old Town - Private Pool - Steps from Duval Street
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $2,503 - $3,273 /wk
 
 
 
 
 

15 reviews write a review

Paradise Found*Luxury Oceanfront Key West 3/2 Oceanside Marina
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD)
 
 
 
 
 

19 reviews write a review

Bahama Dreaming: 3 BR / 2 BA 3 bedroom home in Key West, Sleeps 8
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $465 - $906 /nt
    $2,925 - $6,018 /wk
 
 
 
 
 

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Luxury Spacious Townhouse overlooking Pool w/ water view & 2 Bikes
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $185 - $270 /nt
    $1,166 /wk
 
 
 
 
 

24 reviews write a review

"LITTLE HAVANA SUITE" Beautiful Home w/ Shared Pool. 1 Block to Duval St!
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • sleeps 4
  • baths
  • rates (USD) $188 - $268 /nt
    $1,316 - $2,296 /wk
    $5,640 - $8,040 /mth
 
 
 
 
 

16 reviews write a review

Southard Charm: 3 BR / 2 BA 3 bedroom home in Key West, Sleeps 8
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $400 - $856 /nt
    $2,650 - $5,873 /wk
 
 
 
 
 

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Key West Condo in Truman Annex with Whirlpool Tub, 2 Bikes, & Access to Pool!
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,200 - $2,050 /wk
    $4,000 - $7,000 /mth
 
 
 
 
 

31 reviews write a review

Tucked away near the Southernmost Point, Louisa's Hideaway is it!
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $550 - $780 /nt
    $3,640 - $6,300 /wk
 
 
 
 
 

8 reviews write a review

President's Walk is perfectly located in the Truman Annex
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $1,680 - $2,590 /wk
 
 
 
 
 

10 reviews write a review

Ocean views and beach breezes at La Brisa's #303 West
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $3,000 - $4,000 /mth
 
 
 
 
 

1 reviews write a review

Duval Square Castaway: A condo steps from the action
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $220 - $350 /nt
    $1,470 - $3,010 /wk
 
 
 
 
 

9 reviews write a review

Casa Atlantica: A one bedroom condo on the Atlantic shore of Key West
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $170 - $260 /nt
    $1,120 - $1,820 /wk
 
 
 
 
 

26 reviews write a review

Beach Club #408 - Unique Oceanfront living
Key West Condo Rental Picture
  • bedrooms 4
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $390 - $550 /nt
    $2,590 - $4,410 /wk
 
 
 
 
 

17 reviews write a review

Beach Club #213 - Unique Oceanfront living
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $4,000 - $5,500 /mth
 
 
 
 
 

1 reviews write a review

Beach Club #205 - Unique Oceanfront living
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $4,000 - $5,500 /mth
 
 
 
 
 

1 reviews write a review

Beach Club #201 - Unique Oceanfront living
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $290 - $420 /nt
    $1,890 - $3,500 /wk
 
 
 
 
 

10 reviews write a review

Beach Club #112 - Unique Oceanfront living
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $290 - $420 /nt
    $1,890 - $3,500 /wk
 
 
 
 
 

7 reviews write a review

Beach Club #103 - Unique oceanfront living with breathtaking views
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $290 - $420 /nt
    $1,890 - $3,500 /wk
 
 
 
 
 

18 reviews write a review

Spacious one bedroom condo in the Casa Marina District
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $2,400 - $3,000 /mth
 
 
 
 
 

3 reviews write a review

Elizabeth Retreat: A three bedroom historic home in Old Town
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $5,000 - $6,000 /mth
 
 
 
 
 

3 reviews write a review

Pete's East Cottage: Cypress east cottage steps from Duval
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $260 - $370 /nt
    $1,680 - $2,940 /wk
 
 
 
 
 

11 reviews write a review

Whitehead House: A unique two story home beside the Audubon House
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $370 - $500 /nt
    $2,380 - $4,340 /wk
 
 
 
 
 

22 reviews write a review

Villa Paradiso: A unique mid-town paradise
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $380 - $590 /nt
    $2,450 - $5,110 /wk
 
 
 
 
 

23 reviews write a review

Albury Bungalow: A quiet retreat in the Meadows
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $3,200 - $4,000 /mth
 
 
 
 
 

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South Street Cottage: Bright & sunny in the Casa Marina district
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $3,200 - $7,286 /mth
 
 
 
 
 

3 reviews write a review

Southard Sophistication: Modern Style in Old Town!
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $4,750 - $6,200 /mth
 
 
 
 
 

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Packer Retreat: A beautifully renovated "Conch" house
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $5,500 - $6,500 /mth
 
 
 
 
 

4 reviews write a review

Olivia Cottage: A charming Old Town house near Key West's historic cemetery
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $5,000 - $6,000 /mth
 
 
 
 
 

2 reviews write a review

Dreaming On Duval, A Luxury Residence on Duval
Key West House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $1,000 - $1,800 /nt
    $6,500 - $14,700 /wk
 
 
 
 
 

16 reviews write a review

:: LA PROVENCE @ THE SANCTUARY :: 2 Master Suites / Spa & Walled Courtyard.....
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $3,700 - $7,100 /mth
 
 
 
 
 

6 reviews write a review

Spectacular Atlantic Ocean View Condo At Oceanside Marina
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $290 - $560 /nt
    $1,900 - $3,100 /wk
    $7,800 - $12,800 /mth
 
 
 
 
 

17 reviews write a review

Luxury 2 Bedroom 2.5 Bath Condo On Duval Street. Great Location 'NEW LISTING'
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths
  • rates (USD) $365 - $495 /nt
    $2,236 - $3,150 /wk
    $8,944 - $12,150 /mth
 
 
 
 
 

14 reviews write a review

Garden Oasis Has A Large Tranquil Garden For Outside Enjoyment.
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $225 - $275 /nt
 
 
 
 
 

9 reviews write a review

Carpe Diem - a tropical Conch Cottage in old town Key West -
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $2,707 - $6,067 /mth
 
 
 
 
 

5 reviews write a review

Alegre In Fabulous Key West Awaits
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,800 - $2,700 /wk
    $5,786 - $8,679 /mth
 
 
 
 
 

10 reviews write a review

Bahama House - Tropical Retreat W/ Private Heated Pool/Hot Tub
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD)
 
 
 
 
 

2 reviews write a review

Oceanfront Condominium - Key West Oceanfront at the Coral Reef
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $275 - $499 /nt
    $1,195 - $3,495 /wk
 
 
 
 
 

61 reviews write a review

***Steps from Duval $99-$149 Night - Free Bikes Included!!!***
Key West Studio Rental Picture
  • bedrooms 0
  • rental type Studio
  • sleeps 2
  • baths 1
  • rates (USD) $99 - $149 /nt
 
 
 
 
 

5 reviews write a review

Truman Annex: Southern Palm Self Catering Spacious town home with large deck
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $257 - $471 /nt
    $1,800 - $3,300 /wk
    $5,400 /mth
 
 
 
 
 

39 reviews write a review

Dreaming on Duval
Key West House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 11
  • baths 2
  • rates (USD) $1,000 - $2,100 /nt
    $6,500 - $14,700 /wk
 
 
 
 
 

4 reviews write a review

Casa De Cuba a Beach House - Cuban Flair Steps from Duval
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $510 - $800 /nt
    $3,360 - $5,600 /wk
 
 
 
 
 

14 reviews write a review

"HERON SUITE" Affordable 'Old Town' Studio - Hot Tub - BBQ Grill - Sleeps 4
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $138 - $218 /nt
    $966 - $2,156 /wk
    $4,140 - $6,540 /mth
 
 
 
 
 

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"EGRET SUITE" Cute Cottage w/ Hot Tub Just Steps to The Southernmost Point!
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $138 - $218 /nt
    $966 - $2,156 /wk
    $4,140 - $6,540 /mth
 
 
 
 
 

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"HAVANA HIDEAWAY" - Beautiful Home w/ Pvt Pool Just Steps To Duval
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $358 - $468 /nt
    $2,506 - $3,976 /wk
    $10,740 - $14,040 /mth
 
 
 
 
 

4 reviews write a review

"ARTIST HOUSE @ DUVAL SQUARE" Key West Condo w/ Shared Pool & Pvt Parking
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $258 - $368 /nt
    $1,806 - $3,206 /wk
    $7,740 - $11,040 /mth
 
 
 
 
 

2 reviews write a review

"PAPA'S CATCH" - Shipyard Condo w/ Shared Pool - Walking Distance to Duval St
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,300 - $2,100 /wk
    $3,500 - $7,500 /mth
 
 
 
 
 

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"RETREAT @ TROPICAL VILLAGE" 2nd Story Condo w/ Shared Pool. Close to Beach
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $248 - $338 /nt
    $1,736 - $3,066 /wk
    $7,440 - $10,140 /mth
 
 
 
 
 

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BAHAMA HOUSE Bahamian-Style Home w/ Pvt Pool and Grill. 1/2 Block To Duval St
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $348 - $478 /nt
    $2,436 - $4,116 /wk
    $10,440 - $14,340 /mth
 
 
 
 
 

2 reviews write a review

Perfect Luxury Ultra Modern Ocean View All Amenities Free Wifi
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $450 /nt
    $2,835 /wk
    $7,700 /mth
 
 
 
 
 

24 reviews write a review

POOLSIDE @ TROPICAL VILLAGE - Studio for 2 w/ Shared Pool. Close to ATL Ocean
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $118 - $208 /nt
    $826 - $1,946 /wk
    $3,540 - $6,240 /mth
 
 
 
 
 

2 reviews write a review

Secret Villa - A Key West Hidden Gem in Historic Old Town
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 3
  • rates (USD) $650 - $890 /nt
 
 
 
 
 

13 reviews write a review

ABSOLUTELY PARADISE - Luxury Home w/ Pvt Pool Just 1 Block To Duval St
Key West Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • sleeps 8
  • baths
  • rates (USD) $408 - $618 /nt
    $2,856 - $5,376 /wk
    $12,240 - $18,540 /mth
 
 
 
 
 

1 reviews write a review

"CAYO HUESO HIDEAWAY' - Luxury Monthly Rental - Pvt Pool & Pvt Hot Tub
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $6,500 - $10,179 /mth
 
 
 
 
 

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TROPICAL VILLAGE 6 Homes w/ Pvt Pool & BBQ Grill. Great For Large Parties!
Key West House Rental Picture
  • bedrooms 11
  • rental type House
  • sleeps 32
  • baths 9
  • rates (USD) $1,448 - $2,038 /nt
    $10,136 - $17,766 /wk
    $43,440 - $61,140 /mth
 
 
 
 
 

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"Lovebird Suite" - Adorable & Affordable Cottage- Steps To Southernmost Pt.
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $138 - $218 /nt
    $966 - $2,156 /wk
    $4,140 - $6,540 /mth
 
 
 
 
 

2 reviews write a review

"FALCON SUITE" Affordable Efficiency Cottage w/ BBQ Grill & Hot Tub
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $138 - $218 /nt
    $966 - $2,156 /wk
    $4,140 - $6,540 /mth
 
 
 
 
 

3 reviews write a review

"IBIS SUITE" Secluded Cottage w/ Shared Hot Tub Steps To Southernmost Point
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $138 - $218 /nt
    $966 - $2,156 /wk
    $4,140 - $6,540 /mth
 
 
 
 
 

1 reviews write a review

"SOUTHERN PALMS" Historical Hideaway - Bahama Village - 2 Hot Tubs & Pvt Pool
Key West House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths 4
  • rates (USD) $768 - $1,108 /nt
    $5,376 - $9,506 /wk
    $23,040 - $33,240 /mth
 
 
 
 
 

1 reviews write a review

TRAVELERS' PALM Bahama Village Tree-Top Cottage w/ Pvt Hot Tub & Hammock
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $198 - $298 /nt
    $1,386 - $2,506 /wk
    $5,940 - $8,940 /mth
 
 
 
 
 

3 reviews write a review

"ROYAL PALM" Bahama Village Cottage - Pvt Hot Tub - Perfect for Couples
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $188 - $268 /nt
    $1,316 - $2,296 /wk
    $5,640 - $7,740 /mth
 
 
 
 
 

2 reviews write a review

COCONUT PALM - Bahama Village Home w/ Huge Pvt Hot Tub - Great for Families!
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $408 - $618 /nt
    $2,856 - $5,376 /wk
    $12,240 - $18,540 /mth
 
 
 
 
 

1 reviews write a review

"TOON HALL @ TROPICAL VILLAGE" - Great For Large Groups. Close to ATL Ocean!
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $408 - $618 /nt
    $2,856 - $5,376 /wk
    $12,240 - $18,540 /mth
 
 
 
 
 

4 reviews write a review

Conch Republic Cottages - 3 Bed 3 Bath Group Property - Steps from Duval St!
Key West Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 10
  • baths 3
  • rates (USD) $508 - $778 /nt
    $3,556 - $6,776 /wk
    $15,240 - $23,340 /mth
 
 
 
 
 

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"PORCHSIDE PARADISE" Private Porch & Hot Tub 1/2 Block To Duval St.
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $238 - $298 /nt
    $1,666 - $2,646 /wk
    $7,140 - $8,940 /mth
 
 
 
 
 

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"DECKSIDE 'mini' SUITE" Studio w/ Shared Hot Tub Steps To Duval St
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $138 - $208 /nt
    $966 - $1,876 /wk
    $4,140 - $6,240 /mth
 
 
 
 
 

2 reviews write a review

"ORANGE BLOSSOM SUITE" Cute Condo w/ Loft Half Block To Duval. Shared Hot Tub
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $188 - $268 /nt
    $1,316 - $2,226 /wk
    $5,640 - $8,040 /mth
 
 
 
 
 

2 reviews write a review

Gorgeous 3 Bed 3 Bath w/ Brand New Pool.
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $5,700 - $8,839 /mth
 
 
 
 
 

1 reviews write a review

"SHARK KEY CHATEAU" Incredible 3-Story Mansion w/ Private Beach, Pool, & Spa
Key West House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 14
  • baths 5
  • rates (USD) $19,900 - $26,786 /mth
 
 
 
 
 

1 reviews write a review

(New) Gorgeous 2 Bedroom Two Bathroom In Old Town Key West. Newly Renovated!
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 3
  • rates (USD) $3,800 - $8,036 /mth
 
 
 
 
 

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WINDWARD ISLE - Half Block To Duval St.- Private Hot Tub - Private Parking
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $258 - $348 /nt
    $1,806 - $3,136 /wk
    $7,740 - $10,440 /mth
 
 
 
 
 

7 reviews write a review

"VILLA AZUL" Luxurious Monthly Home w/ Pvt Pool, Deck & Gorgeous Interior.
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $6,800 - $10,982 /mth
 
 
 
 
 

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"VERDE SUITE" - Quiet & Affordable 'Old Town' Cottage - Shared Pool
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $258 /nt
    $1,246 - $2,226 /wk
    $5,340 - $7,740 /mth
 
 
 
 
 

11 reviews write a review

"TRES FLORES" - Private Parking - Just Steps From Duval St - Sleeps up to 10!
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 10
  • baths 3
  • rates (USD) $378 - $618 /nt
    $2,646 - $5,376 /wk
    $11,340 - $18,540 /mth
 
 
 
 
 

3 reviews write a review

"TRADEWINDS" Private Parking - Two Private Hot Tubs - 1/2 Block To Duval!
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths 2
  • rates (USD) $468 - $628 /nt
    $3,276 - $5,796 /wk
    $14,040 - $18,840 /mth
 
 
 
 
 

2 reviews write a review

"TOBAGO HOUSE" Monthly Rental Home w/ Private Pool Just 1 Block To Duval
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $5,000 - $8,036 /mth
 
 
 
 
 

1 reviews write a review

"SHIPYARD" - WEEKLY OR MONTHLY (Truman Annex) - A Short Stroll to Sunset!
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,300 - $2,100 /wk
    $3,500 - $7,550 /mth
 
 
 
 
 

6 reviews write a review

"SECRET GARDEN" - Weekly Or Monthly (Truman Annex) - A Step Above,Steps Away!
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,300 - $2,100 /wk
    $3,500 - $7,550 /mth
 
 
 
 
 

2 reviews write a review

"SEASHORE AT THE SHIPYARD" - Weekly Or Monthly (Truman Annex) Gourmet Kitchen
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,300 - $2,100 /wk
    $3,500 - $7,550 /mth
 
 
 
 
 

2 reviews write a review

"ROMANTIC RETREAT" Private Hot Tub - Very Secluded - Half Block To Duval St.
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $178 - $258 /nt
    $1,246 - $2,226 /wk
    $5,340 - $7,740 /mth
 
 
 
 
 

17 reviews write a review

"SALT POND HIDEAWAY" 2/2 Condo w/ Huge Shared Pool & Hot Tub. Close to Beach!
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,500 - $5,893 /mth
 
 
 
 
 

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Providence Suite - Monthly Rental
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • sleeps 6
  • baths 1
  • rates (USD) $2,500 - $5,089 /mth
 
 
 
 
 

2 reviews write a review

Playa Royale - Monthly Rental
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $2,500 - $6,161 /mth
 
 
 
 
 

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Pinder House - Monthly Rental
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $7,000 - $7,768 /mth
 
 
 
 
 

2 reviews write a review

PASSOVER COTTAGE - Adorable, Historic Home w/ Caribbean Attitude and Pvt Pool
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $378 - $588 /nt
    $2,646 - $4,956 /wk
    $11,340 - $17,640 /mth
 
 
 
 
 

18 reviews write a review

"PARADISE SUITE" Monthly Villa In Gated Complex w/ Pool. Steps to Duval St
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • sleeps 4
  • baths
  • rates (USD) $2,500 - $5,089 /mth
 
 
 
 
 

2 reviews write a review

Palm Isle - Nightly: 1 BR, 1 BA Condominium in Key West, Sleeps 4
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $268 /nt
    $1,246 - $2,296 /wk
    $5,340 - $8,040 /mth
 
 
 
 
 

12 reviews write a review

"PARADISE PALMS" Tropical Key West Home w/ BBQ Grill & Pvt Patio
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $4,000 - $6,696 /mth
 
 
 
 
 

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Osprey`s Nest - Nightly: 1 BR, 1 BA Condominium in Key West, Sleeps 4
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $268 /nt
    $1,246 - $2,296 /wk
    $5,340 - $8,040 /mth
 
 
 
 
 

15 reviews write a review

OLD TOWN GARDEN VILLAS- Sleeps 20. Great For Large Gatherings! 1 Blk To Duval
Key West Townhome Rental Picture
  • bedrooms 5
  • rental type Townhome
  • sleeps 20
  • baths 7
  • rates (USD) $878 - $1,148 /nt
    $6,146 - $10,486 /wk
    $26,340 - $34,440 /mth
 
 
 
 
 

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"MALLORY EFFICIENCY" 1 Block from Duval St. Great KW Deal
Key West Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $138 - $208 /nt
    $966 - $1,876 /wk
    $4,140 - $6,240 /mth
 
 
 
 
 

12 reviews write a review

"LEEWARD ISLE" - Private Hot Tub - Private Parking - 1/2 Block To Duval St.
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $258 - $348 /nt
    $1,806 - $3,136 /wk
    $7,740 - $10,440 /mth
 
 
 
 
 

11 reviews write a review

"LAZY LANE" - WEEKLY OR MONTHLY(Truman Annex) - Color and Style Front to Back
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,400 - $2,100 /wk
    $3,750 - $8,586 /mth
 
 
 
 
 

7 reviews write a review

La Dolce Vita - Luxury Monthly Rental Private heated pool
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 4
  • rates (USD) $9,250 - $12,589 /mth
 
 
 
 
 

1 reviews write a review

"KEY WEST HIDEAWAY" Sleeps Up To 10 - Private Patio - Half Block To Duval!
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $538 - $748 /nt
    $3,766 - $6,636 /wk
    $16,140 - $22,440 /mth
 
 
 
 
 

8 reviews write a review

"ISLAND RENDEZVOUS" Gorgeous Old Town Home w/ Private Pool
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $4,500 - $8,839 /mth
 
 
 
 
 

1 reviews write a review

"HOWE STREET HIDEAWAY" Newly Renovated 2 Bed Two Bath Home.
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $2,500 - $5,625 /mth
 
 
 
 
 

1 reviews write a review

Heron Hideaway - Nightly: 1 BR, 1 BA Condominium in Key West, Sleeps 4
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $268 /nt
    $1,246 - $2,296 /wk
    $5,340 - $8,040 /mth
 
 
 
 
 

12 reviews write a review

Flamingo Hideaway - Private hot tub, Lush landscape
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $268 /nt
    $1,246 - $2,296 /wk
    $5,340 - $8,040 /mth
 
 
 
 
 

14 reviews write a review

Fishtail Hideaway - Monthly Rental
Key West House Rental Picture
  • bedrooms 1
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $2,500 - $5,089 /mth
 
 
 
 
 

2 reviews write a review

"FAMILY HOUSE" Stunning 'Old Town' Home - 1 Block To Duval - Private Hot Tub
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 6
  • baths
  • rates (USD) $268 - $368 /nt
    $1,876 - $3,136 /wk
    $8,040 - $11,040 /mth
 
 
 
 
 

7 reviews write a review

"DUVAL CORNER" - Cute Condo Just off Duval St!-
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $158 - $218 /nt
    $1,106 - $1,666 /wk
    $4,740 - $6,540 /mth
 
 
 
 
 

7 reviews write a review

"DUVAL HIDEAWAY" Nightly Rental w/ Shared Hot Tub. Located On Duval
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $228 - $338 /nt
    $1,596 - $3,066 /wk
    $5,250 - $10,140 /mth
 
 
 
 
 

1 reviews write a review

"CORAL COVE" Affordable Old Town Efficiency - Patio and BBQ Grill
Key West Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $128 - $188 /nt
    $896 - $1,736 /wk
    $3,840 - $5,640 /mth
 
 
 
 
 

12 reviews write a review

"CONCH CASA" - Old Town Home w/ Pvt Hot Tub & Porch. Half a Block To Duval St
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $248 - $338 /nt
    $1,736 - $3,066 /wk
    $7,440 - $10,140 /mth
 
 
 
 
 

8 reviews write a review

"CLAUDE MONET SUITE" Best Deal In KW - Old Town Efficiency - Patio and BBQ
Key West Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $128 - $188 /nt
    $896 - $1,736 /wk
    $3,840 - $5,640 /mth
 
 
 
 
 

17 reviews write a review

"CASA TORTUGA" Monthly Rental. Tropical Condo w/ Pool. A Few Blocks To Duval.
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $4,500 - $8,304 /mth
 
 
 
 
 

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"CASA SERENDIPITY" - World Class Comfort in Lush, Tropical Paradise
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $408 - $618 /nt
    $2,856 - $5,376 /wk
    $12,240 - $18,540 /mth
 
 
 
 
 

10 reviews write a review

"CASA MARGARITA" Amazingly Located Home w/ Pvt Pool & Huge Deck. Pvt Parking
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $408 - $618 /nt
    $2,856 - $5,376 /wk
    $12,240 - $18,540 /mth
 
 
 
 
 

8 reviews write a review

"CASA KEY WEST @ DUVAL SQUARE" Extra Large Condo Located On Duval St.
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 8
  • baths 2
  • rates (USD) $338 - $448 /nt
    $2,366 - $4,046 /wk
    $10,140 - $13,440 /mth
 
 
 
 
 

17 reviews write a review

"CASA CUBANA @ DUVAL SQUARE" Luxurious Condo w/ Pvt Parking & Shared Pool
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $268 - $368 /nt
    $1,876 - $3,206 /wk
    $8,040 - $11,040 /mth
 
 
 
 
 

17 reviews write a review

"CASA BONITA @ DUVAL SQUARE" Luxury Duval St. Condo w/ Shared Pool & Balcony
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 7
  • baths
  • rates (USD) $258 - $358 /nt
    $1,806 - $3,136 /wk
    $7,740 - $10,740 /mth
 
 
 
 
 

14 reviews write a review

"CARIBBEAN SUITE"- Beautiful Home With Shared Pool. 1 Block To Duval
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • sleeps 4
  • baths
  • rates (USD) $198 - $278 /nt
    $1,386 - $2,366 /wk
    $5,940 - $8,340 /mth
 
 
 
 
 

15 reviews write a review

"CASA 625" Monthly Rental w/ Private Pool. Beautiful Interior
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $5,000 - $8,304 /mth
 
 
 
 
 

2 reviews write a review

"BEACH CLUB BREEZE" Monthly Rental - Two Story Home w/ Sun Deck & BBQ Grill
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $4,700 - $6,964 /mth
 
 
 
 
 

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"AMELIA HOUSE" - Private Hot Tub - Half Block To Duval St - Sleeps 8!
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $318 - $428 /nt
    $2,226 - $4,046 /wk
    $9,540 - $12,840 /mth
 
 
 
 
 

15 reviews write a review

"ALEXANDRIA'S SECRET" Luxurious Home w/ Private Pool - 1/2 Block to Duval St
Key West Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • sleeps 8
  • baths
  • rates (USD) $408 - $618 /nt
    $2,856 - $5,376 /wk
    $12,240 - $18,540 /mth
 
 
 
 
 

16 reviews write a review

"SUN ALSO RISES" - Papa`s Hideaway Historic Inn - Studio (2nd Flr)
Key West House Rental Picture
  • bedrooms 0
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $228 /nt
    $1,246 - $2,296 /wk
    $5,340 - $6,840 /mth
 
 
 
 
 

14 reviews write a review

Charming Yacht Located in Exclusive, Beautiful Key West Harbour Yacht Club
Key West Yacht Rental Picture
  • bedrooms 2
  • rental type Yacht
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $165 - $225 /nt
 
 
 
 
 

24 reviews write a review

Boli Townhouse - a Key West Luxury Rental close to everything ! ! !
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,600 - $2,200 /wk
    $6,000 - $8,000 /mth
 
 
 
 
 

26 reviews write a review

Beautiful Tropical House - 2 King Beds! Sleeps 8
Key West Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • sleeps 8
  • baths 3
  • rates (USD) $300 - $462 /nt
    $1,900 - $3,000 /wk
 
 
 
 
 

14 reviews write a review

1/2 Block To Duval, World Of Its Own - Nassau Suite
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 8
  • baths 2
  • rates (USD) $199 - $459 /nt
 
 
 
 
 

1 reviews write a review

Tropical Key West Oasis Private Home 2BR/2 Bath w/ Pool, Weekly Rental
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD)
 
 
 
 
 

40 reviews write a review

Luxurious 4 bedroom/3 full bath home with private pool in Old Town Truman Annex
Key West Townhome Rental Picture
  • bedrooms 4
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $414 - $786 /nt
    $2,900 - $4,900 /wk
 
 
 
 
 

27 reviews write a review

Palm Gardens - Great for Groups!
Key West Condo Rental Picture
  • bedrooms 4
  • rental type Condo
  • sleeps 16
  • baths 4
  • rates (USD) $640 - $968 /nt
    $4,480 - $8,435 /wk
    $19,200 - $29,040 /mth
 
 
 
 
 

1 reviews write a review

The Blue Marlin, Minutes From The Party, Seconds To Paradise.
Key West House_boat Rental Picture
  • bedrooms 1
  • rental type House boat
  • sleeps 4
  • baths 1
  • rates (USD) $180 - $260 /nt
    $1,100 - $1,550 /wk
 
 
 
 
 

1 reviews write a review

Enjoy More Privacy in a Truman Annex End Unit Townhome
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 5
  • baths
  • rates (USD) $200 - $425 /nt
    $1,400 - $2,800 /wk
    $4,200 - $7,800 /mth
 
 
 
 
 

8 reviews write a review

Charming gated community just off Duval, Monthly Rental Only
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 4
  • baths 2
  • rates (USD) $3,267 - $5,133 /mth
 
 
 
 
 

1 reviews write a review

Enjoy Low Off Season Rates Until End of September!
Key West Yacht Rental Picture
  • bedrooms 3
  • rental type Yacht
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $300 - $500 /nt
 
 
 
 
 

12 reviews write a review

Book @ Discounted August Rentals - $325-$350 Base Rate!
Key West House_boat Rental Picture
  • bedrooms 4
  • rental type House boat
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $350 - $500 /nt
 
 
 
 
 

18 reviews write a review

2014 Special Pricing Hemingway Style Cottage/Tropical Pool
Key West Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $2,350 - $3,350 /wk
    $7,950 - $12,500 /mth
 
 
 
 
 

19 reviews write a review

"SOUTHERNMOST SUITES" - 3 Pvt Hot Tubs - BBQ Grill - Sleeps Up to 24!
Key West Cottage Rental Picture
  • bedrooms 6
  • rental type Cottage
  • sleeps 24
  • baths 6
  • rates (USD) $858 - $1,178 /nt
    $6,006 - $11,676 /wk
    $25,740 - $35,340 /mth
 
 
 
 
 

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HIDEAWAY @ TROPICAL VILLAGe - Cozy Condo For 2 w/ Shared Pool
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $298 /nt
    $1,246 - $2,296 /wk
    $5,340 - $8,040 /mth
 
 
 
 
 

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"ROYAL OASIS" - Beautiful 2/2 Monthly Rental w/ Private Heated Pool
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $5,000 - $8,036 /mth
 
 
 
 
 

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"SOUTHERN WIND" Immaculate Home w/ BBQ Grill & Shared Pool. Seconds To Duval
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $1,575 - $2,500 /wk
    $3,800 - $9,264 /mth
 
 
 
 
 

2 reviews write a review

"Shipyard Perch" Weekly or Monthly (Truman Annex) - Gourmet Appointed Kitchen
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $1,400 - $2,400 /wk
    $3,750 - $8,629 /mth
 
 
 
 
 

10 reviews write a review

"SEA BREEZE" - Luxurious 2/1 Condo in Old Town, A Parrot Heads Paradise!
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $208 - $288 /nt
    $1,456 - $2,436 /wk
    $6,240 - $8,640 /mth
 
 
 
 
 

8 reviews write a review

"ISLAND OASIS" Luxury 2 BR 2 Bath Townhome w/ Pvt Heated Pool & Pvt Parking
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $358 - $468 /nt
    $2,506 - $3,976 /wk
    $10,740 - $14,040 /mth
 
 
 
 
 

23 reviews write a review

"CASA HAVANA @ DUVAL SQUARE" 2-Story Condo On Duval St w/ Pvt Hot Tub
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $268 - $368 /nt
    $1,876 - $3,206 /wk
    $8,040 - $11,040 /mth
 
 
 
 
 

15 reviews write a review

"DU PONT HOUSE" Luxury Rental - Private Pool - 1/2 Block To Duval St.
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 6
  • baths 2
  • rates (USD) $368 - $468 /nt
    $2,576 - $4,186 /wk
    $11,040 - $14,040 /mth
 
 
 
 
 

9 reviews write a review

"CASA CARIBE @ DUVAL SQUARE" Beautiful Duval Suare Condo w/ Pvt Hot Tub
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $268 - $368 /nt
    $1,876 - $3,206 /wk
    $8,040 - $11,040 /mth
 
 
 
 
 

9 reviews write a review

"ATLANTIC OCEAN VIEW" - Stylish Condo w/ Spectacular Views
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $248 - $398 /nt
    $1,736 - $3,066 /wk
    $7,440 - $11,940 /mth
 
 
 
 
 

7 reviews write a review

"ABBEY ROAD" Great for Big Parties! - 4 Luxury Units - 4 Private Hot Tubs
Key West Cottage Rental Picture
  • bedrooms 5
  • rental type Cottage
  • sleeps 12
  • baths 4
  • rates (USD) $778 - $1,078 /nt
    $5,446 - $9,296 /wk
    $23,340 - $32,340 /mth
 
 
 
 
 

1 reviews write a review

"SEAPORT SUITE" - Great Party House w/ Hot Tub! 1 Min Walk to Sloppy Joe's
Key West Apartment Rental Picture
  • bedrooms 4
  • rental type Apartment
  • sleeps 12
  • baths 2
  • rates (USD) $468 - $628 /nt
    $3,276 - $5,796 /wk
    $14,040 - $18,840 /mth
 
 
 
 
 

4 reviews write a review

"SPOONBILL SUITE" Affordable Old Town Suite - Hot Tub & BBQ Grill
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $138 - $218 /nt
    $966 - $2,156 /wk
    $4,140 - $6,540 /mth
 
 
 
 
 

1 reviews write a review

"JASMINE SUITE" - Private Parking - Great Location - 1 Block From Duval St.
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $148 - $218 /nt
    $1,036 - $1,946 /wk
    $4,440 - $6,540 /mth
 
 
 
 
 

12 reviews write a review

"DUVAL SQUARE PENTHOUSE" - Gorgeous Condo on Duval St w/ Private Hot Tub
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $268 - $368 /nt
    $1,876 - $3,206 /wk
    $8,040 - $11,040 /mth
 
 
 
 
 

13 reviews write a review

"THE AUDUBON HOUSE" Customer Favorite! Great Location 1 Block To Duval
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $188 - $258 /nt
    $1,316 - $2,226 /wk
    $5,640 - $7,740 /mth
 
 
 
 
 

11 reviews write a review

"ALMOST SOUTHERNMOST" - Private Hot Tub - Half Block To Duval St
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $258 - $348 /nt
    $1,806 - $3,136 /wk
    $7,740 - $10,440 /mth
 
 
 
 
 

1 reviews write a review

Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $4,190 - $7,200 /mth
 
 
 
 
 

8 reviews write a review

TRUMAN @ DUVAL 'Old Town KW' Home Just A Hop-Skip-And-Jump To Duval St.
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $208 - $288 /nt
    $1,456 - $2,436 /wk
    $6,240 - $8,640 /mth
 
 
 
 
 

3 reviews write a review

SOUTHERN CROSS @ TROPICAL VILLAGE - Beautifully Updated Home w/ Shared Pool.
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 6
  • baths 2
  • rates (USD) $268 - $368 /nt
    $1,876 - $3,136 /wk
    $8,040 - $11,040 /mth
 
 
 
 
 

1 reviews write a review

"TRUMAN EFFICIENCY" 1 Block To Duval St. Great KW Deal.
Key West Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $138 - $208 /nt
    $966 - $1,876 /wk
    $4,140 - $6,240 /mth
 
 
 
 
 

10 reviews write a review

"SPA ON DUVAL @ DUVAL SQUARE" Spacious Condo on Duval St w/ Pvt Hot & Parking
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $268 - $368 /nt
    $1,876 - $3,206 /wk
    $8,040 - $11,040 /mth
 
 
 
 
 

13 reviews write a review

TROPICAL RETREAT- Upscale Home w/ Private Pool & BBQ Grill 1/2 Block To Duval
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $408 - $618 /nt
    $2,856 - $5,376 /wk
    $12,240 - $18,540 /mth
 
 
 
 
 

17 reviews write a review

"STARR'S SUITE" Luxury Cottage - Private Hot Tub - Half Block to Duval St!
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $158 - $238 /nt
    $1,106 - $2,156 /wk
    $4,740 - $7,140 /mth
 
 
 
 
 

18 reviews write a review

"POOLSIDE SUITE" - A Few Steps To Duval St! Pvt Parking & Shared Pool!
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $248 - $338 /nt
    $1,736 - $3,066 /wk
    $7,440 - $10,140 /mth
 
 
 
 
 

1 reviews write a review

"POOLSIDE RETREAT" - 1 Block To Duval St. - Shared Pool
Key West House Rental Picture
  • bedrooms 1
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $188 - $288 /nt
    $1,316 - $2,296 /wk
    $5,640 - $8,640 /mth
 
 
 
 
 

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"POOLSIDE PARADISE" Amazing Home 1/2 Block to Duval w/ Pool and Pvt Parking
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $408 - $618 /nt
    $2,856 - $5,376 /wk
    $12,240 - $18,540 /mth
 
 
 
 
 

12 reviews write a review

"McCARTNEY'S MANOR" Luxury Cottage - Private Hot Tub - 1/2 Block To Duval St!
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $188 - $288 /nt
    $1,316 - $2,436 /wk
    $5,640 - $8,640 /mth
 
 
 
 
 

13 reviews write a review

"LENNON'S LODGE" Luxury Vacation Home - Private Hot Tub - 1 Block To Duval St
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 6
  • baths 1
  • rates (USD) $298 - $418 /nt
    $2,086 - $3,626 /wk
    $8,940 - $12,540 /mth
 
 
 
 
 

7 reviews write a review

"HEMINGWAY'S VIEW" - Great Location, 3 BR 2 Bath, Decked Viranda and Hot Tub
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $338 - $458 /nt
    $2,366 - $4,256 /wk
    $10,140 - $13,740 /mth
 
 
 
 
 

13 reviews write a review

HELEN'S HIDEAWAY - Gated, Unique, 2 BR House W/ Private Heated Pool
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $378 - $478 /nt
    $2,646 - $4,116 /wk
    $11,340 - $14,340 /mth
 
 
 
 
 

14 reviews write a review

"HARRISONS HIDEAWAY" Luxury Cottage - Private Hot Tub - Half Block To Duval
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $198 - $288 /nt
    $1,386 - $2,436 /wk
    $5,940 - $8,640 /mth
 
 
 
 
 

7 reviews write a review

"GARDEN OF EDEN" - Papa's Hideaway Historic Inn's 2 BR/2 Bath Cottage
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $288 - $398 /nt
    $2,016 - $3,276 /wk
    $8,640 - $11,940 /mth
 
 
 
 
 

17 reviews write a review

Andros Suite - Nightly: 1 BR, 1.5 BA Townhouse in Key West, Sleeps 4
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • sleeps 4
  • baths
  • rates (USD) $188 - $268 /nt
    $1,316 - $2,226 /wk
    $5,640 - $8,040 /mth
 
 
 
 
 

12 reviews write a review

"ISLANDS IN THE STREAM" - Papa`s Hideaway Historic Inn - Studio (First FlR)
Key West Apartment Rental Picture
  • bedrooms 0
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $228 /nt
    $1,246 - $2,296 /wk
    $5,340 - $6,840 /mth
 
 
 
 
 

15 reviews write a review

Spring & Summer Big Discounts, Great Reviews, Perfect Key West Condo
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths
  • rates (USD) $1,750 - $2,751 /wk
    $6,750 - $9,450 /mth
 
 
 
 
 

24 reviews write a review

Conch Retreat in Key West Truman Annex with 2 Bikes
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,300 - $1,950 /wk
    $4,420 - $6,630 /mth
 
 
 
 
 

29 reviews write a review

:: CASA PLUMERIA @ OLD TOWN SOUTH :: Luxury Home & Guest Cottage / Large Pool...
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $7,500 - $14,000 /mth
 
 
 
 
 

8 reviews write a review

:: OCTOPUS'S GARDEN @ CORAL HAMMOCK :: Spacious Home / Gated + Pool & Fitness...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 3
  • rates (USD) $2,100 - $3,200 /wk
    $7,500 - $11,750 /mth
 
 
 
 
 

17 reviews write a review

:: THE MELLOW MACAW @ SOUTHERNMOST :: Cheerful Condo & Jacuzzi / Block to Duval…
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $290 - $450 /nt
    $1,450 - $2,350 /wk
    $4,900 - $8,250 /mth
 
 
 
 
 

11 reviews write a review

Luxurious 'Old Town' Home - 3BR/3.5BA
Key West Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $295 - $895 /nt
 
 
 
 
 

7 reviews write a review

Home 1/2 Block From Duval Street
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $389 - $429 /nt
 
 
 
 
 

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Coral Cabana - CORAL HAMMOCK townhouse with PORCH VIEWS of the POOL & GARDENS!
Key West Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $200 - $400 /nt
    $1,200 - $2,500 /wk
 
 
 
 
 

3 reviews write a review

Buena Vista Cottage - 1/2 block from Duval Street!!!
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $349 - $389 /nt
 
 
 
 
 

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Sunrise Hideaway #407
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $245 - $319 /nt
 
 
 
 
 

10 reviews write a review

Colony Poolside: A charming bungalow near the historic cemetery
Key West Cabin Rental Picture
  • bedrooms 1
  • rental type Cabin
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $190 - $300 /nt
    $1,260 - $2,240 /wk
 
 
 
 
 

26 reviews write a review

Key West Botel Cold A/c 32 Inch Flat Screen Sleeps 6
Key West Yacht Rental Picture
  • bedrooms 1
  • rental type Yacht
  • sleeps 4
  • baths 1
  • rates (USD) $100 - $125 /nt
    $575 /wk
    $2,500 /mth
 
 
 
 
 

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Book now early bird specials warm winter breaks before rates change!
Key West Yacht Rental Picture
  • bedrooms 2
  • rental type Yacht
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $375 - $1,100 /nt
 
 
 
 
 

37 reviews write a review

Overlooking Famous Duval St. Key West, FL
Key West Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 4
  • baths
  • rates (USD) $435 - $600 /nt
    $3,000 - $3,775 /wk
 
 
 
 
 

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New Home In Old Town
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 4
  • rates (USD) $14,000 /mth
 
 
 
 
 

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HGTV Featured Home - Boaters Paradise! Waterfront Key West Home
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $5,000 /mth
 
 
 
 
 

35 reviews write a review

One of a kind estate 1/2 block from Duval!
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $295 - $895 /nt
 
 
 
 
 

1 reviews write a review

Real World MTV House---Not Just a House Your Own Private Resort
Key West House Rental Picture
  • bedrooms 10
  • rental type House
  • owner badgeowner badge
  • sleeps 20
  • baths
  • rates (USD) $1,500 - $2,500 /nt
    $10,000 - $12,500 /wk
    $40,000 - $50,000 /mth
 
 
 
 
 

28 reviews write a review

Waterfront Luxury in Old Town Key West
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $350 - $480 /nt
    $2,125 - $2,900 /wk
 
 
 
 
 

10 reviews write a review

"A KEY ESCAPE"- Luxury Vacation Rental w/ Private Pool- 1/2 Block To Duval St
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $408 - $618 /nt
    $2,856 - $5,376 /wk
    $12,240 - $18,540 /mth
 
 
 
 
 

22 reviews write a review

4 Palms: 2 BR / 2 BA 2 bedroom condo in Key West, Sleeps 6
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $220 - $381 /nt
    $1,250 - $2,406 /wk
 
 
 
 
 

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A Low Key Paradise, **APRIL 2015 availability**private pool & patio, near beach
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $3,500 - $7,500 /mth
 
 
 
 
 

1 reviews write a review

Private Oasis In The Heart Of Old Town Key West
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $526 - $564 /nt
    $3,300 - $3,950 /wk
 
 
 
 
 

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Southernmost Retreat: 1 Block from Duval in Old Town.
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $288 - $800 /nt
 
 
 
 
 

17 reviews write a review

The Cristol Condo - Classic Key West Oceanfront Charm
Key West Condo Rental Picture
  • bedrooms 4
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 4
  • rates (USD) $849 /nt
 
 
 
 
 

5 reviews write a review

Romantic Spot for Two in Old Town!
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 0
  • rates (USD) $2,100 - $4,667 /mth
 
 
 
 
 

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A Zen Ocean Garden
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $300 - $488 /nt
    $1,800 - $3,250 /wk
 
 
 
 
 

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Coral Villa: 3 BR / 3 BA 3 bedroom condo in Key West, Sleeps 8
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $215 - $394 /nt
    $1,300 - $2,500 /wk
 
 
 
 
 

1 reviews write a review

Key West Charming: 2 BR / 1 BA 2 bedroom condo in Key West, Sleeps 4
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $1,175 - $2,683 /wk
 
 
 
 
 

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Tranquility: 1 BR / 1.5 BA 1 bedroom home in Key West, Sleeps 4
Key West House Rental Picture
  • bedrooms 1
  • rental type House
  • sleeps 4
  • baths
  • rates (USD) $210 - $413 /nt
    $1,175 - $2,465 /wk
 
 
 
 
 

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Tom's 2000sf Direct Oceanfront Penthouse. Renovated, Heated Pool, Close To Beach
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $350 /nt
    $2,200 /wk
    $7,500 /mth
 
 
 
 
 

3 reviews write a review

Coral Hammock - Beautiful Poolside Home (28)
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $250 - $375 /nt
    $1,200 - $2,100 /wk
    $5,500 - $7,000 /mth
 
 
 
 
 

12 reviews write a review

Coral Hammock - Tropical 3 Bedroom Home (4)
Key West Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • sleeps 6
  • baths 3
  • rates (USD) $275 - $375 /nt
    $1,600 - $2,100 /wk
    $5,500 - $7,500 /mth
 
 
 
 
 

2 reviews write a review

Estate Home On The Water With Private Pool And Dockage
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 5
  • rates (USD) $7,875 /wk
 
 
 
 
 

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Elegant European Sail Catamaran Yacht Charter In Private Luxury Marina
Key West Yacht Rental Picture
  • bedrooms 4
  • rental type Yacht
  • sleeps 8
  • baths 4
  • rates (USD) $600 /nt
 
 
 
 
 

1 reviews write a review

Duval Compound, Private Pool, Parking, Roof Deck, Downtown Key West
Key West Villa Rental Picture
  • bedrooms 6
  • rental type Villa
  • owner badgeowner badge
  • sleeps 16
  • baths 6
  • rates (USD)
 
 
 
 
 

6 reviews write a review

Enchanted Garden Compound in Best Old Town Location
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD)
 
 
 
 
 

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:: LA PETITE PENTHOUSE @ THE ANNEX :: Elegantly Furnished / Pool / Near Duval...
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $1,850 - $3,100 /wk
    $6,000 - $10,000 /mth
 
 
 
 
 

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Unobstructed Oceanfront View, 20 Yards To Water
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD)
 
 
 
 
 

1 reviews write a review

The Green Turtle - A Funky Floating Cottage with Direct Ocean Access
Key West House_boat Rental Picture
  • bedrooms 1
  • rental type House boat
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $165 - $240 /nt
    $1,000 - $1,450 /wk
 
 
 
 
 

12 reviews write a review

Ocean Breeze Suites-3 Bd, 3 Bath with loft Sleeps 10
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $695 - $875 /nt
    $4,865 - $6,125 /wk
    $20,850 - $25,500 /mth
 
 
 
 
 

15 reviews write a review

Modern Luxury and Privacy Just Steps from Duval
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $435 - $540 /nt
    $3,000 - $3,600 /wk
 
 
 
 
 

52 reviews write a review

Hide Away @ Truman Annex Gated Community
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $2,217 /wk
    $8,865 /mth
 
 
 
 
 

18 reviews write a review

Historic Key West Estate Located In The Coveted Casa Marina Area.
Key West Estate Rental Picture
  • bedrooms 5
  • rental type Estate
  • sleeps 12
  • baths 3
  • rates (USD) $22,000 - $30,000 /mth
 
 
 
 
 

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Quiet, Quaint And Conveniently Located!
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $85 - $250 /nt
 
 
 
 
 

7 reviews write a review

Egret Cottage: 1 BR / 1 BA 1 bedroom home in Key West, Sleeps 4
Key West House Rental Picture
  • bedrooms 1
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $190 - $384 /nt
    $1,050 - $2,320 /wk
 
 
 
 
 

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Casa Amor - 3BR Residence 2 Blocks from Duval Street
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD)
 
 
 
 
 

13 reviews write a review

:: PERFECT HARMONY @ CASA MARINA :: Heavenly & Private Home / Pavilion & Pool...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 7
  • baths 2
  • rates (USD) $5,000 - $14,000 /mth
 
 
 
 
 

1 reviews write a review

:: SOUTHERNMOST COMFORT @ THE ANNEX:: Roomy & Quiet / Pool / By Duval & Beach...
Key West House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 8
  • baths 4
  • rates (USD) $7,000 - $12,000 /wk
    $25,500 - $42,000 /mth
 
 
 
 
 

1 reviews write a review

Coral Garden: 2 BR / 2.5 BA 2 bedroom condo in Key West, Sleeps 6
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $175 - $338 /nt
    $1,000 - $2,094 /wk
 
 
 
 
 

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Cottage Condo located in the heart of Old Town Key West
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 3
  • baths 1
  • rates (USD) $2,240 - $4,107 /mth
 
 
 
 
 

1 reviews write a review

4 Bedroom, 4 Bath with Pool
Key West House Rental Picture
  • bedrooms 0
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $400 - $1,286 /nt
    $8,000 - $36,000 /mth
 
 
 
 
 

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Annex Luxury - Location and Classic Key West Charm
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $3,289 - $3,989 /wk
 
 
 
 
 

37 reviews write a review

The Dolphin House: 4 BR / 3.5 BA 4 bedroom home in Key West, Sleeps 8
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $4,500 - $10,150 /wk
 
 
 
 
 

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ISLAND DAYS - Fishing, Boating, Golfing, Dining, Shopping!
Key West Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $275 - $429 /nt
 
 
 
 
 

14 reviews write a review

Key West Luxury Vacation Rental 'CLOUD 9' 5 Night Minimum, 1/2 Block From Duval
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $795 - $995 /nt
    $5,565 - $6,965 /wk
 
 
 
 
 

6 reviews write a review

Key West Vacation Rental 'Southard Square Hideaway' Old Town, Pool, Parking Too!
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $2,333 - $4,200 /mth
 
 
 
 
 

1 reviews write a review

5 Star Luxury 4 Bedroom 5.5 Bath - 28 night minimum - AMAZING LOCATION *POOL*
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $7,467 - $14,933 /mth
 
 
 
 
 

1 reviews write a review

10% off Septemer and / or October 'South Street Serenity'
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $5,133 - $8,867 /mth
 
 
 
 
 

2 reviews write a review

The Nautilus - UNWIND IN TRUMAN ANNEX
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths
  • rates (USD) $3,267 - $7,700 /mth
 
 
 
 
 

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:: THE EMERALD ORCHID @ OLD TOWN :: Serene CulDeSac / By Duval / Private Pool...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $7,700 - $18,500 /mth
 
 
 
 
 

1 reviews write a review

Casa De Vino - EXCELLENT PRICE for an amazing townhouse with POOL and TIKi!
Key West Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • sleeps 8
  • baths 3
  • rates (USD) $200 - $400 /nt
    $1,200 - $2,500 /wk
 
 
 
 
 

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:: CASA LOUISA @ OLD TOWN :: Historic / Private Pool & Half a Block Off Duval...
Key West Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $425 - $825 /nt
    $2,550 - $4,500 /wk
    $8,000 - $16,000 /mth
 
 
 
 
 

68 reviews write a review

Sea Breeze Cottage-Gulf View in Truman Annex
Key West Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $2,800 - $3,500 /wk
    $9,520 - $11,900 /mth
 
 
 
 
 

2 reviews write a review

:: IRMA'S ESCAPE @ BUTTERFLY GARDEN :: Tasteful Villa / Gated / Resort Pool.....
Key West Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 4
  • baths
  • rates (USD) $2,500 - $5,850 /mth
 
 
 
 
 

1 reviews write a review

Sea Biscuit - Beautiful Home - Private Pool, Steps to Duval
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $425 - $518 /nt
    $3,625 /wk
 
 
 
 
 

15 reviews write a review

Chick-A-Pea's Cottage:Near Duval-yet private with the comforts of home
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths
  • rates (USD) $464 - $536 /nt
    $3,100 - $3,750 /wk
 
 
 
 
 

9 reviews write a review

Tropical Island Retreat Offers Carefree Relaxing Getaway
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $950 - $1,701 /wk
    $3,750 - $4,500 /mth
 
 
 
 
 

15 reviews write a review

Key West Condo - One And Two Bedrooms
Key West Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $250 /nt
    $1,600 /wk
 
 
 
 
 

3 reviews write a review

:: BELLA PETRONIA @ THE MEADOWS :: Lush & Serene / 11' Ceilings / Pool & Spa....
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $5,500 - $14,500 /mth
 
 
 
 
 

8 reviews write a review

Oceanfront Condominium - Key West's Crown Jewel
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $350 - $484 /nt
    $2,100 - $3,300 /wk
 
 
 
 
 

170 reviews write a review

Harbor Inn Condominium
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,750 - $2,275 /wk
    $6,000 - $8,000 /mth
 
 
 
 
 

9 reviews write a review

Duval Breeze: 2 BR / 2.5 BA 2 bedroom condo in Key West, Sleeps 6
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $225 - $457 /nt
    $1,350 - $2,864 /wk
 
 
 
 
 

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Charming Condo in Old Town Key West's Truman Annex
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $1,300 - $2,400 /wk
    $4,400 - $6,600 /mth
 
 
 
 
 

45 reviews write a review

Rare Penthouse 2 bed/2bath additional King in loft
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $495 - $750 /nt
    $3,465 - $5,250 /wk
    $14,850 - $19,350 /mth
 
 
 
 
 

6 reviews write a review

:: VILLA BAHAMA @ THE ANNEX :: Pristine 3-Story Townhome / Near Duval & Beach...
Key West Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $2,590 - $3,850 /wk
    $6,600 - $13,500 /mth
 
 
 
 
 

28 reviews write a review

Parrotdise - A Tropical Paradise!
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $2,987 - $6,347 /mth
 
 
 
 
 

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Conch Wind: 2 BR / 2 BA 2 bedroom condo in Key West, Sleeps 4
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $265 - $471 /nt
    $1,575 - $2,900 /wk
 
 
 
 
 

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Key West Ginger House
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $215 - $435 /nt
    $1,300 - $2,719 /wk
 
 
 
 
 

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:: CASA FELIZ @ THE SEAPORT :: Lushly Furnished / Large Pool / Near Duval....
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $6,600 - $16,000 /mth
 
 
 
 
 

11 reviews write a review

Family Friendly Beach House With Lush Tropical Gardens
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $8,000 - $9,500 /mth
 
 
 
 
 

1 reviews write a review

Luxury Condominiums Key West Harbour
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 5
  • baths
  • rates (USD) $359 - $489 /nt
 
 
 
 
 

1 reviews write a review

Special Discounted Rates For Sept. - Ocean Side Luxury On Smather's Beach
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,987 - $6,300 /mth
 
 
 
 
 

1 reviews write a review

Key West Dreamin' - Downtown Location with a Private Pool
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $386 - $457 /nt
    $2,500 - $3,200 /wk
 
 
 
 
 

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Exclusive Key West Beach Front - Amazing View of the Ocean.
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 3
  • rates (USD) $364 - $443 /nt
    $2,150 - $3,100 /wk
 
 
 
 
 

1 reviews write a review

Down Island Digs - Ideal Location Downtown, Private Pool.
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $364 - $425 /nt
    $2,200 - $2,975 /wk
 
 
 
 
 

1 reviews write a review

The Meeting Point - Key West - Elegant and Grand
Key West Estate Rental Picture
  • bedrooms 11
  • rental type Estate
  • sleeps 26
  • baths 0
  • rates (USD) $1,879 - $2,325 /nt
    $11,400 - $14,750 /wk
 
 
 
 
 

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Secret Courtyard Cottage - Downtown with Privacy!
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 5
  • baths 1
  • rates (USD) $261 - $300 /nt
    $1,500 - $1,975 /wk
 
 
 
 
 

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Heavenly Hideout at Key West Mile Zero ~ Mallory Square only 3 Blocks Away!
Key West Apartment Rental Picture
  • bedrooms 4
  • rental type Apartment
  • sleeps 8
  • baths 4
  • rates (USD) $543 - $600 /nt
    $3,400 - $4,200 /wk
 
 
 
 
 

1 reviews write a review

Tropical Tranquility - 5 Star Caribbean Resort-Style Villa
Key West Villa Rental Picture
  • bedrooms 4
  • rental type Villa
  • sleeps 8
  • baths
  • rates (USD) $800 - $1,050 /nt
    $4,550 - $6,200 /wk
 
 
 
 
 

1 reviews write a review

Island Oasis Garden Home - Hidden in the Heart of Old Town
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 4
  • baths 2
  • rates (USD) $1,650 - $2,350 /wk
 
 
 
 
 

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Crowner's Jewel: 2 BR / 2.5 BA 2 bedroom condo in KEY WEST, Sleeps 6
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $1,550 - $3,081 /wk
 
 
 
 
 

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Key West Found: 2 BR / 2.5 BA 2 bedroom condo in KEY WEST, Sleeps 6
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $1,650 - $3,553 /wk
 
 
 
 
 

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Hands Down Best Value In Key West
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $220 - $280 /nt
    $1,395 - $1,925 /wk
    $5,200 - $6,750 /mth
 
 
 
 
 

5 reviews write a review

:: HAVANA HOUSE @ SOLARES HILL :: Elegant Cottage & Private Pool / Near Duval...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $6,000 - $11,500 /mth
 
 
 
 
 

7 reviews write a review

:: TOBA'S TREE HOUSE @ CASA EAST :: Breezy Cottage & Pool / 1 Block to Beach....
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $3,900 - $7,700 /mth
 
 
 
 
 

2 reviews write a review

Oceanside Marina, Stock Island, Key West
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD)
 
 
 
 
 

7 reviews write a review

Single Family Home, 3 Bedroom, 2 Bath, Pool and Electric Car, Great Value!
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $2,800 - $3,733 /mth
 
 
 
 
 

9 reviews write a review

The Quarterdeck - COLORFUL & COMFORTABLE unit in The Shipyard at TRUMAN ANNEX!
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $995 - $2,000 /wk
    $3,800 - $6,000 /mth
 
 
 
 
 

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:: GOOD DAY, SUNSHINE ! @ OLD TOWN :: Sunny & Near Duval / Large Porch & Pool…..
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $4,800 - $11,500 /mth
 
 
 
 
 

5 reviews write a review

Petronia Palms for Budget Minded by Duval St Has a Large Pool!
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD)
 
 
 
 
 

29 reviews write a review

Petronia Palms, Just Off Duval St.Safe! and Has a Large Pool!
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

18 reviews write a review

Petronia Palms, Just Off Duval St. Sleeps 6 Has a Large Pool! Hot-Tub
Key West House Rental Picture
  • bedrooms 0
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 0
  • rates (USD) $1,750 - $2,250 /wk
    $7,000 - $8,700 /mth
 
 
 
 
 

5 reviews write a review

Petronia Palms, Just Off Duval St. Safe! and Has a Large Pool!
Key West House Rental Picture
  • bedrooms 1
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

38 reviews write a review

Key West Rental (Casa De Suenos) House of Dreams! and a Pool!!
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

22 reviews write a review

Petronia Palms, Just Off Duval St.Safe! and Has a Large Pool!
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

38 reviews write a review

Top Of Duval-Penthouse Suites
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 16
  • baths 6
  • rates (USD) $1,076 - $2,370 /nt
    $5,900 - $8,500 /wk
 
 
 
 
 

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:: WINDOWS ON THE GULF @ THE ANNEX :: Oceanfront / Luxurious Penthouse / Pool...
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $3,250 - $5,500 /wk
    $9,000 - $19,000 /mth
 
 
 
 
 

21 reviews write a review

:: GULFSIDE VISTAS @ THE ANNEX :: Oceanfront / Lavish Penthouse Condo & Pool....
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $3,850 - $5,900 /wk
    $8,800 - $19,500 /mth
 
 
 
 
 

39 reviews write a review

Galleon Resort Efficiency Historic District
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $219 - $299 /nt
    $1,573 - $2,093 /wk
    $6,730 - $7,770 /mth
 
 
 
 
 

3 reviews write a review

:: SUNSET DREAMS 2 @ FLORIDA BAY :: Luxurious / Waterfront Condo / Pool & Spa...
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $3,150 - $6,600 /mth
 
 
 
 
 

4 reviews write a review

:: SUNSET VISTAS @ SUNSET MARINA :: Beautiful Waterfront Condo / Pool & Spa.....
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $2,800 - $6,600 /mth
 
 
 
 
 

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:: AVALYNN HOUSE @ THE ANNEX :: Lush Home & Lagoon Pool / Near Beach & Duval....
Key West House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $9,250 - $12,500 /wk
    $18,000 - $44,500 /mth
 
 
 
 
 

27 reviews write a review

:: CONCH CASA GRANDE @ THE ANNEX :: Lush / 6 Master BR's / Pool & Near Duval....
Key West House Rental Picture
  • bedrooms 7
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 7
  • rates (USD) $10,500 - $14,000 /wk
    $18,000 - $49,000 /mth
 
 
 
 
 

31 reviews write a review

:: SOUTHERNMOST HOSPITALITY @ UPPER DUVAL :: Lavish / 5 Bedroom Suites & Pool...
Key West Estate Rental Picture
  • bedrooms 5
  • rental type Estate
  • sleeps 12
  • baths 5
  • rates (USD) $1,200 - $2,100 /nt
    $7,000 - $12,000 /wk
    $25,500 - $42,000 /mth
 
 
 
 
 

16 reviews write a review

Key West, Just do it! And bring the family!
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $225 - $265 /nt
    $1,475 - $1,700 /wk
 
 
 
 
 

2 reviews write a review

:: AZURE MORNING @ OCEANSIDE MARINA :: Lavish Oceanfront Condo / Pool & Spa.....
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $2,100 - $3,200 /wk
    $7,500 - $11,750 /mth
 
 
 
 
 

16 reviews write a review

:: SEAFARER'S REFUGE @ PARADISE HARBOR :: Spacious Home / Private Pool & Slip...
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $7,500 - $14,000 /mth
 
 
 
 
 

1 reviews write a review

:: SUNSET DREAMS @ FLORIDA BAY :: Luxury Bayfront Condo / Marina / Pool & Spa...
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $4,200 - $7,750 /mth
 
 
 
 
 

3 reviews write a review

Enchanting Historic Home in the Heart of Old Town Key West
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $5,133 - $12,133 /mth
 
 
 
 
 

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Oceanfront
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

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Beautiful Duval St. Condo, Location, Location!!!!
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $250 - $300 /nt
    $1,200 - $1,600 /wk
    $4,500 - $6,000 /mth
 
 
 
 
 

27 reviews write a review

:: EDEN @ THE ANNEX :: Old Town Villa / Community Pool / Near Duval & Beach.....
Key West Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,850 - $3,100 /wk
    $6,000 - $10,800 /mth
 
 
 
 
 

21 reviews write a review

Gated Private Luxurious Getaway-Truman Annex (Private Pool)
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 4
  • rates (USD)
 
 
 
 
 

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:: MAISON TROPICALE @ SOLARES HILL :: Stunning / Near Duval / Pool & Spa...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $6,600 - $15,000 /mth
 
 
 
 
 

3 reviews write a review

:: POOLSIDE RETREAT @ THE CLUB :: Cozy Villa / Resort Pool / Gated Community....
Key West Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $3,150 - $6,000 /mth
 
 
 
 
 

3 reviews write a review

:: MAHOGANY HOUSE @ THE MEADOWS :: Breathtaking / By Duval / Pavilion & Pool....
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $7,000 - $17,000 /mth
 
 
 
 
 

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:: CASA DE ROSALIE @ BAYVIEW PARK :: Historic Home & Pool / By Tennis Courts....
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $4,500 - $9,950 /mth
 
 
 
 
 

2 reviews write a review

:: THE BICYCLE COTTAGE @ OLD TOWN :: Iconic Cottage / By Duval / Private Pool...
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 6
  • baths 2
  • rates (USD) $4,000 - $8,800 /mth
 
 
 
 
 

2 reviews write a review

Key West 3 Bedroom Condo- Direct Beach Front
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 8
  • baths 3
  • rates (USD)
 
 
 
 
 

1 reviews write a review

:: HEAVENLY ZEN @ THE SEAPORT :: Lavish Old Town Home & Pool / Close to Duval...
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $10,000 - $20,000 /mth
 
 
 
 
 

12 reviews write a review

Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio
Key West Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $400 - $651 /nt
    $2,800 - $4,560 /wk
 
 
 
 
 

32 reviews write a review

Céad Míle Fáilte - a Thousand Welcomes to Our Innisfree
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,400 - $1,925 /wk
 
 
 
 
 

10 reviews write a review

:: COOL BREEZE @ THE ANNEX :: Impeccably Furnished Villa / Near Duval + Pool....
Key West Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $2,590 - $3,850 /wk
    $6,600 - $13,500 /mth
 
 
 
 
 

24 reviews write a review

Carey's Conch Cottage Old Town, Key West, Private Heated Pool
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $4,200 - $6,067 /mth
 
 
 
 
 

17 reviews write a review

Truman Annex Flamingo Beach Garden Level
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

27 reviews write a review

HISTORIC RESTORED 'EYEBROW' HOME. REDUCED PRICES!!!
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $6,067 - $7,933 /mth
 
 
 
 
 

9 reviews write a review

:: NOONA*S MANSION-by-the-SEA @ THE ANNEX :: Large Estate & Pool / Near Duval...
Key West House Rental Picture
  • bedrooms 7
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths
  • rates (USD) $11,500 - $15,200 /wk
    $40,000 - $55,000 /mth
 
 
 
 
 

42 reviews write a review

Beach house exclusive private resort island 500 yards from heart of Key West
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 0
  • rates (USD) $27,067 - $30,933 /mth
 
 
 
 
 

6 reviews write a review

Oceanfront Condo with beautiful sunset views 2 blocks from Duval St.
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $2,660 - $3,850 /wk
    $7,980 - $11,900 /mth
 
 
 
 
 

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Old Town Beauty built in 1883
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 7
  • baths 1
  • rates (USD) $3,267 - $4,480 /mth
 
 
 
 
 

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Perfect Cottage with Private Pool and Garden-2bed/2bath
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD)
 
 
 
 
 

2 reviews write a review

:: SUNSET'S SOLACE @ SUNSET MARINA :: Bayfront / 2 Master Suites / Pool & Spa...
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $2,800 - $6,600 /mth
 
 
 
 
 

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:: PARADISE PERFECTED @ SMATHERS BEACH :: Modern Home & Pool / Block to Beach...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $5,000 - $13,000 /mth
 
 
 
 
 

3 reviews write a review

:: VILLA OLIVIETTA @ SOLARES HILL :: Lush & Large / Near Duval / Private Pool...
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $9,500 - $20,000 /mth
 
 
 
 
 

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:: CAYO CALYPSO @ HIGGS BEACH :: Brand New / Near Duval & Beach / Private Pool..
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $5,000 - $9,950 /mth
 
 
 
 
 

2 reviews write a review

:: SWEET CAROLINES SANCTUARY @ THE SEAPORT :: Condo / Near Duval / Pool & Spa...
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $3,150 - $6,000 /mth
 
 
 
 
 

4 reviews write a review

:: MURIELS WHIMSICAL GALLERIA @ OLD TOWN :: Vaulted Ceilings / Balcony on Duval…
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $3,150 - $6,750 /mth
 
 
 
 
 

2 reviews write a review

:: NANCY'S COASTAL COMFORT @ FLORIDA BAY :: Waterfront & Pool / Large & Airy....
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $5,500 - $12,500 /mth
 
 
 
 
 

1 reviews write a review

:: WATERSIDE RETREAT @ KEY HAVEN :: Faces Bay & Canal / 40' Dock & Boat Lift....
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $6,000 - $9,500 /mth
 
 
 
 
 

1 reviews write a review

:: HIDDEN TREASURE @ CASA EAST :: Luxurious / Enormous Pool / Close to Beach....
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $5,700 - $15,000 /mth
 
 
 
 
 

13 reviews write a review

:: CASA BLANCA 1888 @ WHITE :: Historic / Old Town / Very Large Yard & Pool.....
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $8,000 - $17,500 /mth
 
 
 
 
 

17 reviews write a review

:: TROPICAL JEWEL @ THE SEAPORT :: Cozy Cottage & Large Pool / Near Duval...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $5,500 - $11,500 /mth
 
 
 
 
 

6 reviews write a review

:: TOP O’ THE TOWN @ THE SEAPORT :: Lavish / 13 Foot Ceilings & Private Pool...
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $5,500 - $15,000 /mth
 
 
 
 
 

5 reviews write a review

True Key West Experience! Coastal Living's Artists Paradise!
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $4,000 /mth
 
 
 
 
 

4 reviews write a review

:: SOUTHERN STAR @ THE SEAPORT :: Impeccably Restored / Large Pool / By Duval...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $7,700 - $18,000 /mth
 
 
 
 
 

13 reviews write a review

Key West Retreat at Marriott Beachside
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD)
 
 
 
 
 

41 reviews write a review

:: SUNSET POINT @ SUNSET MARINA :: Bayfront Luxury Condo / Pool & Spa / Marina..
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $4,200 - $7,750 /mth
 
 
 
 
 

2 reviews write a review

CALICO COVE -- Charming, Key West apartment nestled in Old Town.
Key West Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

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Waterfront Views from Dolphin Watch
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD)
 
 
 
 
 

2 reviews write a review

Grand Four Bedroom Home, Ideal Location, with Dipping Pool
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $200 - $400 /nt
 
 
 
 
 

2 reviews write a review

4 Bedroom, 3 Bath Private Home With Pool For Monthly Rental
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $5,600 - $7,653 /mth
 
 
 
 
 

3 reviews write a review

Bungalow Breeze - Old Town Cottage with POOL & PRIVATE DECK!
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $1,867 - $3,687 /mth
 
 
 
 
 

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Pet-Friendly
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $5,600 /mth
 
 
 
 
 

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Casa Marina - True Island Elegance!
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $6,067 - $10,733 /mth
 
 
 
 
 

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Ocean View Key West Condo
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

1 reviews write a review

Amazing Grace - Monthly Rental
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,411 - $2,306 /wk
    $6,048 - $9,884 /mth
 
 
 
 
 

4 reviews write a review

Santa Maria Suites Resort - Luxury Two Bedroom Pool View Suite
Key West Hotel Rental Picture
  • bedrooms 2
  • rental type Hotel
  • sleeps 4
  • baths 2
  • rates (USD) $499 - $1,600 /nt
 
 
 
 
 

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Santa Maria Suites Resort - Luxury Two Bedroom
Key West Hotel Rental Picture
  • bedrooms 2
  • rental type Hotel
  • sleeps 4
  • baths 1
  • rates (USD) $439 - $900 /nt
 
 
 
 
 

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Santa Maria Suites Resort - Luxury Two Bedroom Pool View Bi-Level Suite
Key West Hotel Rental Picture
  • bedrooms 2
  • rental type Hotel
  • sleeps 4
  • baths 2
  • rates (USD) $469 - $1,300 /nt
 
 
 
 
 

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Santa Maria Suites Resort - One Bedroom Suite
Key West Hotel Rental Picture
  • bedrooms 1
  • rental type Hotel
  • sleeps 2
  • baths 1
  • rates (USD) $419 - $800 /nt
 
 
 
 
 

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Perfectly Positioned On Sunset Key - 500 Yards Off-shore Key West
Key West Villa Rental Picture
  • bedrooms 5
  • rental type Villa
  • sleeps 12
  • baths 6
  • rates (USD) $18,000 - $25,000 /mth
 
 
 
 
 

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Bring Your Boat! Key West Waterfront Vacation Home.
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $3,500 - $3,900 /wk
    $9,500 - $10,900 /mth
 
 
 
 
 

2 reviews write a review

The Golden Heron
Key West House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths 4
  • rates (USD)
 
 
 
 
 

1 reviews write a review

'Tropical Splendor' 3 bd luxury condo&ocean view at Oceanside Marina.
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 7
  • baths 2
  • rates (USD) $300 - $500 /nt
    $1,500 - $3,000 /wk
    $6,000 - $10,800 /mth
 
 
 
 
 

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200 Feet From Duval. Perfect Location.
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $275 /nt
    $1,733 /wk
 
 
 
 
 

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Secluded, Private, Tropical Retreat In Old Town, Key West.
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 6
  • baths 2
  • rates (USD) $365 - $480 /nt
    $2,300 - $3,024 /wk
    $8,176 - $10,752 /mth
 
 
 
 
 

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Old Town Cottages
Key West Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 8
  • baths 3
  • rates (USD)
 
 
 
 
 

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Beautiful House in the BEST Location in Key West!
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $4,200 - $10,220 /mth
 
 
 
 
 

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To the Nines - Penthouse Villa with Balcony Over Duval Street
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $7,250 - $10,150 /mth
 
 
 
 
 

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Anderson's Key West Home
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $1,100 /nt
 
 
 
 
 

4 reviews write a review

Upscale Vacation Rentals in Old Town Key West
Key West Villa Rental Picture
  • bedrooms 1
  • rental type Villa
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

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Close to Duval Street, but quiet and secluded
Key West Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

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Historic Compound in Old Key West
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD)
 
 
 
 
 

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