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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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DEAL!! Baya House - a great old town location
Key West Townhome Rental Picture
  • Townhome Rental Deals and Discounts 30% off = $1,470 per week
  • bedrooms 2
  • community Windward Park
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,300 - $2,500 /wk
    $4,500 - $5,500 /mth
 
 
 
 
 

13 reviews write a review

DEAL!! Emma House & Cottage Plus Pvt. Pool
Key West House Rental Picture
  • House Rental Deals and Discounts $500 off = $2,950 per week
  • House Rental Deals and Specials Housekeeping ($150)
  • bedrooms 3
  • community Truman Annex
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $2,250 - $5,500 /wk
    $9,000 - $17,500 /mth
 
 
 
 
 

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DEAL!! La Brisa Beachfront Condo
Key West Condo Rental Picture
  • Condo Rental Deals and Discounts 20% off = $1,440 per week
  • Condo Rental Deals and Specials no cleaning fees ($100)
  • bedrooms 2
  • community La Brisa Condos
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $250 - $425 /nt
    $1,600 - $2,800 /wk
 
 
 
 
 

12 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

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) $290 - $300 /nt
    $1,995 - $2,100 /wk
 
 
 
 
 

2 reviews write a review

Attitude Key West At the Beach
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
 
 
 
 
 

18 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
 
 
 
 
 

32 reviews write a review

Surf Side - Fabulous Ocean Front Condo
Key West Condo Rental Picture
  • bedrooms 3
  • community 1800 Atlantic
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $375 - $636 /nt
    $2,350 - $4,170 /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 - $6,000 /mth
 
 
 
 
 

31 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

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) $188 - $278 /nt
    $1,250 - $1,800 /wk
 
 
 
 
 

34 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

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
 
 
 
 
 

7 reviews write a review

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
 
 
 
 
 

38 reviews write a review

The Cristol Condo
Key West Condo Rental Picture
  • bedrooms 4
  • community Harbour Place
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 4
  • rates (USD) $749 - $1,595 /nt
    $3,989 - $6,989 /wk
    $11,989 - $21,489 /mth
 
 
 
 
 

5 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
 
 
 
 
 

7 reviews write a review

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) $120 - $230 /nt
    $780 - $1,600 /wk
 
 
 
 
 

30 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) $1,125 - $2,100 /wk
 
 
 
 
 

9 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
 
 
 
 
 

17 reviews write a review

Ocean Paradise
Key West House Rental Picture
  • bedrooms 3
  • community Truman Annex
  • rental type House
  • sleeps 8
  • baths 4
  • rates (USD) $5,200 - $12,500 /wk
 
 
 
 
 

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Ocean Retreat
Key West Townhome Rental Picture
  • bedrooms 3
  • community Truman Annex
  • rental type Townhome
  • sleeps 5
  • baths
  • rates (USD) $3,200 - $7,500 /wk
 
 
 
 
 

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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
 
 
 
 
 

9 reviews write a review

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
 
 
 
 
 

41 reviews write a review

Attitude Key West
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
 
 
 
 
 

18 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
 
 
 
 
 

7 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
 
 
 
 
 

62 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) $208 - $288 /nt
    $1,250 - $1,800 /wk
 
 
 
 
 

29 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) $975 - $1,600 /wk
 
 
 
 
 

16 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
 
 
 
 
 

28 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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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) $295 - $525 /nt
    $1,855 - $3,325 /wk
    $6,625 - $7,925 /mth
 
 
 
 
 

35 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

Classic Key West Charm
Key West House Rental Picture
  • bedrooms 3
  • community Truman Annex
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $549 - $859 /nt
    $2,789 - $4,289 /wk
    $8,995 - $16,495 /mth
 
 
 
 
 

37 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

Ocean Vista
Key West Condo Rental Picture
  • bedrooms 2
  • community La Brisa Condos
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $225 - $325 /nt
    $1,575 - $2,100 /wk
    $3,000 - $4,500 /mth
 
 
 
 
 

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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

A Touch of Bermuda in Key West
Key West Cottage Rental Picture
  • 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
 
 
 
 
 

7 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

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

Beachfront Home, Key's only real Beach house,private/gated.
Key West House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $3,750 - $4,800 /wk
 
 
 
 
 

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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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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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Oceanfront,gated,tropical,private estate
Key West House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $15,000 - $18,000 /mth
 
 
 
 
 

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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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Key West Botel Cold a/c 32 inch flat screen sleeps 6
Key West Houseboat Rental Picture
  • bedrooms 1
  • community
  • rental type Houseboat
  • sleeps 6
  • baths 1
  • rates (USD) $74 - $100 /nt
 
 
 
 
 

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

3 reviews write a review

Private 58ft Yacht in Paradise!
Key West Houseboat Rental Picture
  • bedrooms 3
  • community
  • rental type Houseboat
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $275 - $450 /nt
 
 
 
 
 

2 reviews write a review

A Very Special Conch House
Key West House Rental Picture
  • bedrooms 2
  • community Old Town
  • rental type House
  • sleeps 4
  • baths
  • rates (USD) $3,500 - $4,500 /mth
 
 
 
 
 

1 reviews write a review

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 2bed/1bath condo in premier downtown location
Key West Condo Rental Picture
  • bedrooms 2
  • community Truman Annex
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,050 - $1,900 /wk
 
 
 
 
 

10 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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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

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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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

Spacious Charming Key West House
Key West House Rental Picture
  • bedrooms 3
  • community Midtown
  • rental type House
  • sleeps 11
  • baths 2
  • rates (USD) $3,300 - $3,700 /mth
 
 
 
 
 

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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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Most Unique Rental in Paradise! MV Coconuts!
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
 
 
 
 
 

10 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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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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a captains retreat
Key West House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $6,000 - $7,000 /mth
 
 
 
 
 

1 reviews write a review

Key West Harbour Oceanfront Suites
Key West Condo Rental Picture
  • 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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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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"Bird's Nest" Golf Course Home on Lagoon
Key West Villa Rental Picture
  • bedrooms 2
  • community Key West Golf Club
  • rental type Villa
  • sleeps 4
  • baths
  • rates (USD) $1,800 - $6,000 /mth
 
 
 
 
 

1 reviews write a review

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----April-May special
Key West Condo Rental Picture
  • bedrooms 1
  • community
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $2,400 - $6,400 /mth
 
 
 
 
 

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Oceanfront, private and gated 5 acre estate
Key West House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $6,500 - $7,500 /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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Oceanfront, gated and private 5 acre estate in Key West
Key West House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $7,500 - $8,500 /mth
 
 
 
 
 

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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

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) $250 - $485 /nt
    $1,395 - $3,395 /wk
 
 
 
 
 

51 reviews write a review

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
 
 
 
 
 

15 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 - $9,500 /mth
 
 
 
 
 

5 reviews write a review

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

1 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) $200 - $250 /nt
 
 
 
 
 

5 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)
 
 
 
 
 

2 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

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

3 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

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) $190 - $225 /nt
 
 
 
 
 

22 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

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 - $220 /nt
    $1,000 - $1,300 /wk
 
 
 
 
 

11 reviews write a review

"Royal Oasis" - Beautiful 2/2 Monthly Rental W/ Heated Pool.
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $5,000 - $8,000 /mth
 
 
 
 
 

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Windward Isle
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $258 - $448 /nt
    $3,136 /wk
 
 
 
 
 

3 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) $5,133 - $7,700 /mth
 
 
 
 
 

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(New Addition) Luxurious 5 Bedroom Mansion w/ Private Beach!
Key West House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 14
  • baths 5
  • rates (USD) $18,667 - $25,667 /mth
 
 
 
 
 

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AFFORDABLE NIGHTLY RENTAL 1 BLOCK FROM DUVAL ST! 'TRUMAN EFFICIENCY' WELL KEP
Key West Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $138 - $268 /nt
    $1,876 /wk
 
 
 
 
 

6 reviews write a review

Villa Azul - Monthly Rental
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $6,067 - $9,100 /mth
 
 
 
 
 

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Sunset Suite
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $208 - $348 /nt
    $2,436 /wk
 
 
 
 
 

3 reviews write a review

Tobago
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $4,667 - $6,767 /mth
 
 
 
 
 

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Tradewinds Sleeps up to 12
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths 2
  • rates (USD) $468 - $828 /nt
    $5,796 /wk
 
 
 
 
 

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Shipyard Perch - Weekly or Monthly (Truman Annex)
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $1,400 - $2,400 /wk
    $3,750 - $5,500 /mth
 
 
 
 
 

5 reviews write a review

Shipyard - Weekly Or Monthly (Truman Annex)
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,300 - $2,100 /wk
    $3,500 - $6,000 /mth
 
 
 
 
 

2 reviews write a review

Seabreeze - Luxurious 2/1 Condo in Old Town Key West. A Parrot Heads Paradise
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $208 - $348 /nt
    $2,436 /wk
 
 
 
 
 

2 reviews write a review

Seashore At The Shipyard - Weekly Or Monthly (Truman Annex)
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,300 - $2,100 /wk
    $3,500 - $6,000 /mth
 
 
 
 
 

1 reviews write a review

Secret Garden - Weekly Or Monthly (Truman Annex)
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,300 - $2,100 /wk
    $3,500 - $6,000 /mth
 
 
 
 
 

1 reviews write a review

Romantic Retreat
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $178 - $318 /nt
    $2,226 /wk
 
 
 
 
 

7 reviews write a review

Salt Pond Hideaway - Monthly Rental
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,333 - $4,433 /mth
 
 
 
 
 

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Playa Royale - Monthly Rental
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $3,267 - $5,367 /mth
 
 
 
 
 

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Paradise Suite - Monthly Rental
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • sleeps 4
  • baths
  • rates (USD) $2,333 - $4,433 /mth
 
 
 
 
 

2 reviews write a review

Passover Cottage
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $378 - $708 /nt
    $4,956 /wk
 
 
 
 
 

5 reviews write a review

Pinder House - Monthly Rental
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $6,533 - $6,767 /mth
 
 
 
 
 

2 reviews write a review

Palm Isle
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $328 /nt
    $2,296 /wk
 
 
 
 
 

7 reviews write a review

Paradise Palms - Monthly Rental
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $3,733 - $5,833 /mth
 
 
 
 
 

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Palm Gardens - Great for Groups!
Key West Condo Rental Picture
  • bedrooms 4
  • rental type Condo
  • sleeps 16
  • baths 4
  • rates (USD) $528 - $888 /nt
    $6,216 /wk
 
 
 
 
 

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Old Town Garden Villas - Sleeps up to 20!
Key West Townhome Rental Picture
  • bedrooms 5
  • rental type Townhome
  • sleeps 20
  • baths 7
  • rates (USD) $878 - $1,448 /nt
    $10,136 /wk
 
 
 
 
 

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Oceania Suite
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $318 /nt
    $2,226 /wk
 
 
 
 
 

5 reviews write a review

Monroe Efficiency
Key West Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $138 - $268 /nt
    $1,876 /wk
 
 
 
 
 

5 reviews write a review

AFFORDABLE NIGHTLY RENTAL 1 BLOCK FROM DUVAL ST! 'MALLORY EFFICIENCY' WELL KE
Key West Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $138 - $268 /nt
    $1,876 /wk
 
 
 
 
 

7 reviews write a review

Leeward Isle - Half a block from Duval!
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $258 - $448 /nt
    $3,136 /wk
 
 
 
 
 

5 reviews write a review

Island Rendezvous - Monthly Rental
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $4,200 - $7,700 /mth
 
 
 
 
 

1 reviews write a review

Howe Street Hideaway - Monthly Rental
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $2,333 - $4,900 /mth
 
 
 
 
 

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Heron Hideaway
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $328 /nt
    $2,296 /wk
 
 
 
 
 

4 reviews write a review

Havana Hideaway
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $268 - $468 /nt
    $3,276 /wk
 
 
 
 
 

4 reviews write a review

Fleming O House - 2Br 1Bath House by Duval Street! A Favorite! Sleeps up to 6
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $228 - $438 /nt
    $3,066 /wk
 
 
 
 
 

5 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 - $328 /nt
    $2,296 /wk
 
 
 
 
 

6 reviews write a review

Fishtail Hideaway - Monthly Rental
Key West House Rental Picture
  • bedrooms 1
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $2,333 - $4,433 /mth
 
 
 
 
 

1 reviews write a review

Duval Hideaway - Monthly Rental
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $3,267 - $4,900 /mth
 
 
 
 
 

1 reviews write a review

Cozy Condo in Prime Location, Duval Corner 1/2 block off of Duval St!
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $138 - $298 /nt
    $2,086 /wk
 
 
 
 
 

6 reviews write a review

Conch Casa
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $248 - $438 /nt
    $3,066 /wk
 
 
 
 
 

1 reviews write a review

Claude Monet Suite
Key West Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $118 - $248 /nt
    $1,736 /wk
 
 
 
 
 

8 reviews write a review

Casa Tortuga - Monthly Rental
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $4,200 - $7,233 /mth
 
 
 
 
 

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Casa Cubana
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $268 - $468 /nt
    $3,276 /wk
 
 
 
 
 

8 reviews write a review

Boardwalk Loft - Monthly Rental
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $2,567 - $4,433 /mth
 
 
 
 
 

1 reviews write a review

Casa 625 is an address and house of distinction! - Monthly Rental
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $4,200 - $7,233 /mth
 
 
 
 
 

1 reviews write a review

Bermuda Suite
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • sleeps 4
  • baths
  • rates (USD) $188 - $328 /nt
    $2,296 /wk
 
 
 
 
 

8 reviews write a review

Beach Club Breeze - Monthly Rental
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $4,667 - $6,767 /mth
 
 
 
 
 

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'THE AUDUBON HOUSE' EFFICIENCY AT ITS FINEST! CUSTOMER FAVORITE!
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $188 - $318 /nt
    $2,226 /wk
 
 
 
 
 

5 reviews write a review

Andros Suite
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • sleeps 4
  • baths
  • rates (USD) $188 - $318 /nt
    $2,226 /wk
 
 
 
 
 

4 reviews write a review

''ABACO SUITE'' - A KEY WEST CUSTOMER FAVORITE! SLEEPS 4 COMFORTABLY
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $318 /nt
    $2,226 /wk
 
 
 
 
 

1 reviews write a review

Sun Also Rises - Papa`s Hideaway Historic Inn - Studio (Second Floor)
Key West House Rental Picture
  • bedrooms 0
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $139 - $249 /nt
    $1,743 /wk
 
 
 
 
 

6 reviews write a review

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
 
 
 
 
 

26 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) $8,633 - $10,967 /mth
 
 
 
 
 

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Coral Cove - Freshly renovated
Key West Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $128 - $248 /nt
    $1,736 /wk
 
 
 
 
 

6 reviews write a review

Southernmost Retreat
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $248 - $438 /nt
    $3,066 /wk
 
 
 
 
 

7 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
 
 
 
 
 

17 reviews write a review

Island Oasis
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $358 - $568 /nt
    $3,976 /wk
 
 
 
 
 

6 reviews write a review

Casa Margarita
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $408 - $768 /nt
    $5,376 /wk
 
 
 
 
 

1 reviews write a review

Casa Key West
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 8
  • baths 2
  • rates (USD) $338 - $598 /nt
    $4,186 /wk
 
 
 
 
 

6 reviews write a review

Key West Hideaway
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $538 - $948 /nt
    $6,636 /wk
 
 
 
 
 

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Casa Serendipity
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $408 - $768 /nt
    $5,376 /wk
 
 
 
 
 

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Helen`s Hideaway Private Heated Pool
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $388 - $588 /nt
    $4,116 /wk
 
 
 
 
 

7 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

Amelia House
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $318 - $578 /nt
    $4,046 /wk
 
 
 
 
 

9 reviews write a review

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
 
 
 
 
 

8 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) $4,200 - $7,000 /mth
 
 
 
 
 

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Family House - Stunning 2-Br 1.5-Ba w/PVT Hot Tub! Walking distance to Duval
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 6
  • baths
  • rates (USD) $268 - $448 /nt
    $3,136 /wk
 
 
 
 
 

3 reviews write a review

ROMANTIC GETAWAY SPOT. 'HONEYMOON HIDEAWAY' VERY PRIVATE :)
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $178 - $318 /nt
    $2,226 /wk
 
 
 
 
 

9 reviews write a review

AFFORDABLE NIGHTLY RENTAL 1 BLOCK FROM DUVAL! 'HIBISCUS EFFICIENCY'
Key West Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $128 - $258 /nt
    $1,806 /wk
 
 
 
 
 

4 reviews write a review

Casa Grande
Key West House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 14
  • baths
  • rates (USD) $768 - $1,398 /nt
    $9,786 /wk
 
 
 
 
 

3 reviews write a review

Hemingway's View
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $338 - $608 /nt
    $4,256 /wk
 
 
 
 
 

3 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) $900 - $1,500 /nt
    $6,090 - $14,700 /wk
 
 
 
 
 

14 reviews write a review

Poolside Retreat
Key West House Rental Picture
  • bedrooms 1
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $188 - $328 /nt
    $2,296 /wk
 
 
 
 
 

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Poolside Suite
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $248 - $438 /nt
    $3,066 /wk
 
 
 
 
 

1 reviews write a review

IMMACULATE KEY WEST VACATION RENTAL - 'ALEXANDRIA'S SECRET' - PRIVATE POOL
Key West Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • sleeps 8
  • baths
  • rates (USD) $408 - $768 /nt
    $5,376 /wk
 
 
 
 
 

7 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
 
 
 
 
 

9 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
 
 
 
 
 

2 reviews write a review

Old Town Beauty built in 1883
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 7
  • baths 1
  • rates (USD) $3,500 - $10,000 /mth
 
 
 
 
 

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Poolside Paradise
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $408 - $768 /nt
    $5,376 /wk
 
 
 
 
 

4 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)
 
 
 
 
 

1 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
 
 
 
 
 

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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)
 
 
 
 
 

1 reviews write a review

KEY WEST HOT SPOT! 'ALMOST SOUTHERNMOST' CLOSE TO SOUTHERNMOST POINT - SLEEP
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 1
  • rates (USD) $258 - $448 /nt
    $3,136 /wk
 
 
 
 
 

2 reviews write a review

Casa Bonita - Beautiful 2/2.5 Condo w/ Pool on Duval Street! Sleeps up to 7!
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 7
  • baths
  • rates (USD) $258 - $458 /nt
    $3,206 /wk
 
 
 
 
 

5 reviews write a review

DuPont House - Private Heated Pool
Key West Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 6
  • baths 2
  • rates (USD) $368 - $598 /nt
    $4,186 /wk
 
 
 
 
 

6 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

Providence Suite - Monthly Rental
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • sleeps 6
  • baths 1
  • rates (USD) $2,333 - $4,433 /mth
 
 
 
 
 

1 reviews write a review

Atlantic Ocean View
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $288 - $438 /nt
    $3,066 /wk
 
 
 
 
 

1 reviews write a review

Almost Southernmost Too
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $378 - $668 /nt
    $4,676 /wk
 
 
 
 
 

4 reviews write a review

Almost Southernmost Retreat - Sleeps up to 16!
Key West House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 16
  • baths
  • rates (USD) $638 - $1,248 /nt
    $8,736 /wk
 
 
 
 
 

3 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
 
 
 
 
 

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Verde Suite
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $318 /nt
    $2,226 /wk
 
 
 
 
 

3 reviews write a review

Tres Flores - Sleeps up to 10!
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 10
  • baths 3
  • rates (USD) $378 - $768 /nt
    $5,376 /wk
 
 
 
 
 

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Starr's Suite
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $178 - $318 /nt
    $2,226 /wk
 
 
 
 
 

5 reviews write a review

Spa on Duval Gorgeous 2-Br 2.5-Ba Condo w/ Pvt Hot Tub! Located on Duval Stre
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $268 - $468 /nt
    $3,276 /wk
 
 
 
 
 

5 reviews write a review

Osprey’s Nest
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $178 - $328 /nt
    $1,386 - $2,296 /wk
 
 
 
 
 

7 reviews write a review

A KEY WEST HOT SPOT! 'McCartney's Manor' PRIVATE HOT TUB!
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $198 - $348 /nt
    $2,436 /wk
 
 
 
 
 

7 reviews write a review

Little Havana Suite
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • sleeps 4
  • baths
  • rates (USD) $188 - $328 /nt
    $2,296 /wk
 
 
 
 
 

10 reviews write a review

Lennon's Lodge
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 6
  • baths 1
  • rates (USD) $298 - $518 /nt
    $3,626 /wk
 
 
 
 
 

4 reviews write a review

Lazy Lane - Weekly or Monthly (Truman Annex)
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,300 - $2,400 /wk
    $3,750 - $6,500 /mth
 
 
 
 
 

4 reviews write a review

LUXURY & LOCATION! A GREAT GETAWAY SPOT FOR TWO :) 'JASMINE SUITE'
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $148 - $278 /nt
    $1,946 /wk
 
 
 
 
 

6 reviews write a review

Duval Square Penthouse
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $268 - $468 /nt
    $3,276 /wk
 
 
 
 
 

5 reviews write a review

Casa Caribe
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $268 - $468 /nt
    $3,276 /wk
 
 
 
 
 

3 reviews write a review

'A KEY ESCAPE' - LOCATION & LUXURY - 1 BLOCK FROM DUVAL - SLEEPS UP TO 8
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $408 - $768 /nt
    $5,376 /wk
 
 
 
 
 

10 reviews write a review

Whom the Bell Tolls - Papas Hideaway's Deluxe Studio 3
Key West House Rental Picture
  • bedrooms 0
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $149 - $259 /nt
    $1,813 /wk
 
 
 
 
 

4 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

Tropical Retreat
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $408 - $768 /nt
    $5,376 /wk
 
 
 
 
 

8 reviews write a review

Special April 2014 Monthly Rate - Key West Ocean Side Luxury On Smather's Beach
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $3,547 - $6,300 /mth
 
 
 
 
 

1 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) $285 - $530 /nt
    $1,800 - $3,000 /wk
    $6,800 - $11,000 /mth
 
 
 
 
 

5 reviews write a review

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 - $1,345 /wk
 
 
 
 
 

22 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
 
 
 
 
 

38 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)
 
 
 
 
 

17 reviews write a review

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

3 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 - $220 /nt
 
 
 
 
 

14 reviews write a review

Caribbean Suite
Key West Townhome Rental Picture
  • bedrooms 1
  • rental type Townhome
  • sleeps 4
  • baths
  • rates (USD) $198 - $338 /nt
    $2,366 /wk
 
 
 
 
 

7 reviews write a review

Islands In the Stream - Papa`s Hideaway Historic Inn - Studio (First Floor)
Key West House Rental Picture
  • bedrooms 0
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $139 - $249 /nt
    $1,743 /wk
 
 
 
 
 

6 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)
 
 
 
 
 

158 reviews write a review

Abbey Road - Great for Big Parties! 4 Units w/ 4 PVT Hot Tubs Key West Favori
Key West Cottage Rental Picture
  • bedrooms 5
  • rental type Cottage
  • sleeps 12
  • baths 4
  • rates (USD) $778 - $1,328 /nt
    $9,296 /wk
 
 
 
 
 

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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
 
 
 
 
 

19 reviews write a review

Unique Vacation Rental on Water! Available Fantasy Fest Week Starting Oct. 27th!
Key West Yacht Rental Picture
  • bedrooms 3
  • rental type Yacht
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $250 - $500 /nt
 
 
 
 
 

10 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

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
 
 
 
 
 

1 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
 
 
 
 
 

10 reviews write a review

Harrison's Hideaway
Key West Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $198 - $348 /nt
    $2,436 /wk
 
 
 
 
 

4 reviews write a review

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) $1,400 - $2,050 /wk
    $4,800 - $7,000 /mth
 
 
 
 
 

29 reviews write a review

Garden of Eden - Papas Hideaway Historic Inn's 2br/2ba cottage
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $268 - $468 /nt
 
 
 
 
 

9 reviews write a review

LUXURY & LOCATION! A GREAT GETAWAY SPOT FOR TWO :) 'ORCHID SUITE'
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $148 - $278 /nt
    $1,946 /wk
 
 
 
 
 

4 reviews write a review

Casa De Mango
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $268 - $468 /nt
    $3,276 /wk
 
 
 
 
 

4 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)
 
 
 
 
 

4 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) $495 - $895 /nt
 
 
 
 
 

1 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
    $1,250 - $2,256 /wk
 
 
 
 
 

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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

'HIDDEN TREASURE @ CASA EAST': Luxurious 3BR 3BA Villa & Huge Pool near Beach...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $5,320 - $14,000 /mth
 
 
 
 
 

12 reviews write a review

'THE SEAFARER'S REFUGE @ PARADISE HARBOR': Old Town Home By Water + Pool & Dock.
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $7,000 - $13,067 /mth
 
 
 
 
 

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) $1,400 - $4,000 /wk
    $6,000 /mth
 
 
 
 
 

37 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
 
 
 
 
 

24 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

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
 
 
 
 
 

7 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
 
 
 
 
 

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'VILLA BAHAMA @ THE FOUNDRY': Luxury 2BR/2.5BA Townhome in Truman Annex...
Key West Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $2,000 - $3,750 /wk
    $6,600 - $13,500 /mth
 
 
 
 
 

25 reviews write a review

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
 
 
 
 
 

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Southard Charm: 3 BR / 2.0 BA house in Key West, Sleeps 8
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $400 - $855 /nt
    $2,650 - $5,872 /wk
 
 
 
 
 

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'AZURE MORNING @ OCEANSIDE MARINA': Lavish Oceanfront Condo + Pool....
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

'OLD TOWN OASIS @ TRUMAN ANNEX': Luxurious 2BR/2BA Condo + Oceanside Pool...
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $2,400 - $3,950 /wk
    $8,750 - $14,500 /mth
 
 
 
 
 

40 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

Excellent Value - Coral Cabana - Beautiful Townhome overlooking Pool and Tiki
Key West Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $230 - $400 /nt
    $1,360 - $2,500 /wk
 
 
 
 
 

2 reviews write a review

Grand Four Bedroom Home, Ideal Location, with Dipping Pool
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $200 - $300 /nt
 
 
 
 
 

1 reviews write a review

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
 
 
 
 
 

1 reviews write a review

Trusted Sailing Charter Adventures Since 1995 and three blocks to Duval
Key West Yacht Rental Picture
  • bedrooms 2
  • rental type Yacht
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD)
 
 
 
 
 

25 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)
 
 
 
 
 

5 reviews write a review

“SOUTHERNMOST HOSPITALITY @ UPPER DUVAL”: Superlative 5BR/5.5BA Estate + 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 - $41,000 /mth
 
 
 
 
 

9 reviews write a review

Excellent Price for an Amazing Townhome with Pool and Tiki Bar
Key West Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • sleeps 8
  • baths 3
  • rates (USD) $230 - $400 /nt
    $1,360 - $2,500 /wk
 
 
 
 
 

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'NOONA'S MANSION-by-the-SEA @ THE ANNEX' The Ultimate 7BR Estate + Pool...
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
 
 
 
 
 

37 reviews write a review

Truman Annex: Paradise Lost Self Catering Unique ground floor condominium
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $214 - $400 /nt
    $1,500 - $2,800 /wk
    $4,500 /mth
 
 
 
 
 

36 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

Sunrise Hideaway #407
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $255 - $319 /nt
    $1,925 - $2,065 /wk
    $4,000 - $5,500 /mth
 
 
 
 
 

6 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) $418 - $514 /nt
    $3,600 /wk
 
 
 
 
 

11 reviews write a review

New Potter's Cottage -Private Pool, Quiet, Yet Steps Off Duval
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD)
 
 
 
 
 

13 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) $457 - $521 /nt
    $3,100 - $3,650 /wk
 
 
 
 
 

7 reviews write a review

'PUERTA CORALINA @ SOLARES HILL': Charming 2BR/3BA Cottage + Private Pool...
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
 
 
 
 
 

48 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

Quiet, Quaint And Conveniently Located!
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $120 - $180 /nt
 
 
 
 
 

4 reviews write a review

“HAVANA HOUSE @ SOLARES HILL”: Simply Elegant 3BR/2BA Cottage + Pool..
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $5,600 - $10,733 /mth
 
 
 
 
 

1 reviews write a review

'BELLA PETRONIA @ THE MEADOWS: 3BR/3.5BA Private Home With Pool & Jacuzzi...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $4,667 - $13,533 /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
    $1,250 - $2,256 /wk
 
 
 
 
 

5 reviews write a review

'CASA LOUISA @ UPPER DUVAL': Historic Conch Cottage & Pool 1/2 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
 
 
 
 
 

64 reviews write a review

'EDEN @ THE ANNEX': 2BR/1.5BA Old Town Villa near Beach & Sunset Pier...
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
 
 
 
 
 

12 reviews write a review

'THE COMMODORE'S MANOR @ PARADISE HARBOR ': Grand 5BR/4BA Waterfront Home + 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
    $6,900 - $10,000 /wk
    $20,000 - $33,000 /mth
 
 
 
 
 

40 reviews write a review

'GULFSIDE VISTAS @ TRUMAN ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo...
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $3,500 - $5,750 /wk
    $9,900 - $19,500 /mth
 
 
 
 
 

34 reviews write a review

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

5 reviews write a review

'MAISON TROPICALE @ SOLARES HILL': Lush 3BR/3BA Old Town Home, Pool & Spa...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $6,160 - $14,000 /mth
 
 
 
 
 

3 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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'SUNSET DREAMS 2 @ FLORIDA BAY': Luxurious 2BR/2BA Waterfront Condo...
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $2,940 - $6,160 /mth
 
 
 
 
 

4 reviews write a review

'LA PROVENCE @ THE SANCTUARY': 2 Master Suites, Spa Pool with Walled Yard...
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $3,267 - $6,627 /mth
 
 
 
 
 

6 reviews write a review

'THE BICYCLE COTTAGE @ OLD TOWN': Iconic 2BR/2BA Lovely Island Cottage...
Key West Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 6
  • baths 2
  • rates (USD) $3,733 - $7,000 /mth
 
 
 
 
 

2 reviews write a review

'COOL BREEZE @ THE ANNEX': Meticulously Furnished 2BR/2.5BA Old Town Villa...
Key West Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $2,000 - $3,750 /wk
    $6,600 - $13,500 /mth
 
 
 
 
 

16 reviews write a review

'CONCH CASA GRANDE @ THE ANNEX': Enormous 7BR/7BA in Truman Annex...
Key West House Rental Picture
  • bedrooms 7
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 7
  • rates (USD) $9,500 - $13,500 /wk
    $30,000 - $49,000 /mth
 
 
 
 
 

20 reviews write a review

'CASA PLUMERIA @ OLD TOWN SOUTH': 4BR/3.5BA Home & Guest Cottage + Pool...
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $7,000 - $13,067 /mth
 
 
 
 
 

6 reviews write a review

'AZURE AFTERNOON @ OCEANSIDE MARINA': Serene 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
 
 
 
 
 

13 reviews write a review

“CAYO CALYPSO @ HIGGS BEACH”: 3BR/3BA New Tropical Home + Private Pool...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $5,133 - $9,287 /mth
 
 
 
 
 

1 reviews write a review

'SOUTHERNMOST COMFORT @ THE ANNEX': Stunning 5BR/4BA Private Home + Pool...
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
 
 
 
 
 

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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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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

Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 7
  • baths 2
  • rates (USD) $3,990 - $6,900 /mth
 
 
 
 
 

4 reviews write a review

'CASA, SUITE CASA @ CASA MARINA': Lavish New Home W/ 4 Suites + Pool...
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 5
  • rates (USD) $8,400 - $18,667 /mth
 
 
 
 
 

4 reviews write a review

'SUNSET DREAMS @ FLORIDA BAY': Luxury 3BR/2BA Waterfront Condo by Marina...
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $3,920 - $7,233 /mth
 
 
 
 
 

3 reviews write a review

“VILLA OLIVIETTA @ SOLARES HILL” - Exceptional 4BR/5BA Home + Private Pool...
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $8,867 - $18,667 /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

'THE LILAC COTTAGE @ SOLARES HILL': 2.5BR/2BA Old Town Cottage, Quiet Street...
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $4,667 - $10,733 /mth
 
 
 
 
 

2 reviews write a review

'TROPICAL JEWEL @ THE SEAPORT': 2BR/2BA Lovely Old Town Cottage + Pool...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $5,133 - $10,733 /mth
 
 
 
 
 

5 reviews write a review

“MURIEL'S WHIMSICAL GALLERIA @ DUVAL STREET”: Dreamy 2BR/2BA Downtown Condo...
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $2,940 - $6,300 /mth
 
 
 
 
 

2 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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'POOLSIDE RETREAT @ THE POOL': Poolside 2BR/2.5BA Villa with 2 Master Suites...
Key West Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $2,940 - $5,600 /mth
 
 
 
 
 

3 reviews write a review

“THE CAPTAIN'S ANNEX @ PARADISE HARBOR”: Ample 4BR Home + Pool & Boat Slip...
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $650 - $1,000 /nt
    $4,000 - $6,000 /wk
    $14,000 - $21,000 /mth
 
 
 
 
 

8 reviews write a review

'FLAMINGO DREAMS @ SOLARES HILL': Pristine 3BR/2BA Conch Home in Old Town...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $5,320 - $14,000 /mth
 
 
 
 
 

6 reviews write a review

'CASA BLANCA 1888 @ WHITE': Historic 4BR/3BA Old Town Home + Very Large Pool....
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $7,467 - $16,333 /mth
 
 
 
 
 

15 reviews write a review

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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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)
 
 
 
 
 

19 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)
 
 
 
 
 

8 reviews write a review

Condo In Historic 1928 Conch House, Walking Distance To Duval
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $2,500 - $3,500 /mth
 
 
 
 
 

6 reviews write a review

'SUNSET VISTAS @ SUNSET MARINA': Lovely 2BR/2BA Waterfront Condo + Pool...
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $2,940 - $6,160 /mth
 
 
 
 
 

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Enchanted Garden Compound in Best Old Town Location
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD)
 
 
 
 
 

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'CASA FELIZ @ THE SEAPORT': Lushly Furnished 3BR/3.5BA Private Home + Pool...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $6,160 - $14,933 /mth
 
 
 
 
 

8 reviews write a review

'IRMA'S ESCAPE @ THE BUTTERFLY GARDEN': Tasteful 2BR/2.5BA Villa + Resort Pool
Key West Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 4
  • baths
  • rates (USD) $2,800 - $5,460 /mth
 
 
 
 
 

1 reviews write a review

'NATALIE'S BAHAMA CONCH' @ THE SANCTUARY': Lush 3BR/2.5BA Home, Pool...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $4,667 - $8,913 /mth
 
 
 
 
 

4 reviews write a review

'NANCY'S SEASIDE RETREAT @ THE FLORIDA BAY': Waterfront 4BR/4BA Home + Pool..
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $5,600 - $11,667 /mth
 
 
 
 
 

1 reviews write a review

'NANCY'S COASTAL COMFORT @ THE FLORIDA BAY': Waterfront 4BR/3.5BA Home + Pool..
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $5,600 - $11,667 /mth
 
 
 
 
 

1 reviews write a review

“BAHAMIAN BAMBOO @ THE ANNEX”: Beautifully Furnished 3BR/3BA Home + Pool...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $4,800 - $6,975 /wk
    $18,000 - $25,000 /mth
 
 
 
 
 

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A Low Key Paradise *NEW PICTURES, Spacious home, private pool, close to beach
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $3,500 - $6,500 /mth
 
 
 
 
 

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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)
 
 
 
 
 

18 reviews write a review

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

'HEAVENLY ZEN @ THE SEAPORT': Lavish 4BR/3BA Old Town Home + Pool....
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $9,333 - $18,667 /mth
 
 
 
 
 

9 reviews write a review

'TOP O' THE TOWN @ THE HISTORIC SEAPORT': 3BR/3.5BA FIVE STAR LUXURY CONDO...
Key West Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $5,133 - $14,000 /mth
 
 
 
 
 

3 reviews write a review

Peaceful Palace w/ Gorgeous Surroundings In Old Town Key West. Windward Park #9
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $1,575 - $2,500 /wk
    $5,000 - $9,000 /mth
 
 
 
 
 

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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

“GOOD DAY, SUNSHINE! @ OLD TOWN”: Sunny 2BR/2BA Cottage + Large Porch & Pool…
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $4,667 - $10,733 /mth
 
 
 
 
 

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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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'SOUTHERN STAR @ THE SEAPORT'' Renovated Historic 3BR/3BA Home with Pool...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $7,187 - $16,800 /mth
 
 
 
 
 

11 reviews write a review

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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'PARADISE PERFECTED @ SMATHERS BEACH': Handsome Beach House + Pool...
Key West House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $4,667 - $12,133 /mth
 
 
 
 
 

3 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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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
    $7,518 - $10,878 /wk
 
 
 
 
 

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'PORTSIDE MANSION @ THE SEAPORT': Magnificent 3-Building Compound + Large Pool..
Key West Estate Rental Picture
  • bedrooms 6
  • rental type Estate
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD) $17,733 - $27,067 /mth
 
 
 
 
 

8 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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'SWEET CAROLINE'S SANCTUARY @ THE SEAPORT': Cozy 1BR/1BA Condo + Pool, Spa...
Key West Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $2,940 - $5,600 /mth
 
 
 
 
 

3 reviews write a review

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

1 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)
 
 
 
 
 

26 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

Most Beautiful Sunsets In Key West
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,002 - $2,450 /wk
 
 
 
 
 

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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

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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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

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

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)
 
 
 
 
 

20 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)
 
 
 
 
 

36 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)
 
 
 
 
 

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Old Town Cottages
Key West Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 8
  • baths 0
  • 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) $4,900 - $7,000 /mth
 
 
 
 
 

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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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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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Large, Beautiful and Private Home Waterfront Luxury Living
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 4
  • rates (USD)
 
 
 
 
 

4 reviews write a review

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)
 
 
 
 
 

1 reviews write a review

'Casa Amorita' - Luxury In The Heart Of Old Town
Key West Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $4,107 /mth
 
 
 
 
 

3 reviews write a review

Artist House
Key West Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $268 - $358 /nt
 
 
 
 
 

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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
 
 
 
 
 

4 reviews write a review

Havana Hideaway, Downtown, Pool, Parking, 1 Block Off Duval
Key West House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD)
 
 
 
 
 

3 reviews write a review

Anderson's Key West Home
Key West House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $990 /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 10
  • baths 2
  • rates (USD)
 
 
 
 
 

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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)
 
 
 
 
 

34 reviews write a review