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Vacation Rentals in Islamorada, Florida

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about Islamorada

Islamorada, Florida Vacation Rentals and Tourism

For your next vacation, head south and discover what the Florida Keys have to offer by reserving your Islamorada lodging through Vacation Rentals.com. Islamorada, Florida Keys rentals are as conveniently located to Islamorada attractions as Islamorada hotels, but they provide you with something Islamorada hotels cannot - a sense of being at home. Live like a local in one of these many house rentals; Islamorada deserves your undivided attention after all! Truly become a part of this fisherman's paradise.

This colorful series of keys, given the Spanish name "purple island" by early Spanish explorers, has its own pace and way of life. The strict ordinances against over-development ensure that you'll experience a destination much different from the many other areas of Florida's coast. Eschewing formula retail chains, Islamorada condo rentals fit the "lack of a façade" that's the defining characteristic of the area.

So, if you're ready to trade strip malls for some of the best sports fishing in the country, check out one of the many homes for rent in Islamorada for your next vacation. These Islamorada Keys house rentals provide all the comforts of home, including laundry machines, Wi-Fi Internet access, big-screen televisions, and fully-furnished kitchens, so you can cook what you catch rather than spending all of your money in Islamorada restaurants.

Give more than just a glance to Islamorada accommodations; Florida Keys vacation rentals are best researched on Vacation Rentals.com. Choose an Islamorada vacation rental as your next home in Islamorada.

There's no better place to relax than at Islamorada.  It's time you treat yourself to a vacation away from it all, staying in a luxurious but affordable Islamorada vacation rental!  Among all the beaches and boat rides, don't let your budget get in the way of having fun and feeling stress-free.  With great deals and discounts on Islamorada vacation rentals, you can choose from any of our low-price high value condos, town homes or beach houses.  Our spacious, yet budget friendly options are perfect for a large group or for you and that special someone to enjoy a luxurious and affordable Islamorada rental home. So don't let money stop you from enjoying the sunsets, electric boat rides and relaxing on your Islamorada vacation, because our list of comfy, cheap Islamorada vacation rentals has your great deal already taken care of.

 

more destinations

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

Islamorada things to do

 

Paddle The Florida Keys

I went back once again last weekend because it's the only place with this friendly and cool of a staff! Scott the owner is a great guy! His staff is very...read more

 

Robbie's of Islamorada

The rental boats are in need of serious attention. I understand they are rentals and get abused but it should not take 5-15 mins every time you go to start...read more

 

History of Diving Museum

On our way to the keys I spotted this place WOW just take your time and look around it's really interesting. Everybody had a good time museum was well put...read more

 

Theater of the Sea

This place rocks. Had a blast with my wife and 2 kids (under 10). Really a great flow to the shows and you are SO close to all the animals. My daughter...read more

 

Anne's Beach

Parking is extremely limited as there is only about 8-9 parking spaces available and one must wait for someone else to leave in order to park. Beach itself...read more

 

Grouchy Turtle

My boyfriend and I had a great time on a Sunset Cruise with Grouchy Turtle Tours recently! There is nothing like watching the sunset in the keys from the...read more

 

Conch Republic Divers

I had to change my review since it's been about 8 years since I started diving with Conch Republic. All of the staff is great and helpful. Brenda has a...read more

 

Islamorada Boat Tours

It's moved across Whale Harbor to the Holiday Isle. Great boat and crew that delivered good viz. and a great time. Crew explained what was going on and...read more

 

Key Dives

8th time back to Key Dives in as many years. What a terrific group. Happy, pleasant, friendly, professional. My (then) 9 year old daughter earned her open...read more

 

Islamorada Dive Center

I dove with Islamorada Dive Center on 7/28/14. At first I was worried because the boat held so many people, but then discovered there were many guides and...read more

 

Bud N' Mary's Fishing Marina

Horrific! I booked a trip for a total of 6 people a year in advance. I called every few months to make sure we were still good to go. I had people flying...read more

 

Florida Keys Dive Center

If you get seasick, this might not be the trip for you. We went out on a snorkeling trip with a huge group of people - all ages, all fitness levels (it was...read more

 

Indian Key State Historic Site

Pretty fun to kayak to. There is no beach but you can check out tiny fish and hermit crabs while 'snorkeling' around the mangroves. Other than that, it's...read more

 

Island Explorers Watersports

Wow! That about sums up our day trip to the keys.. We heard about island explorers from a friend so we booked a half day rental which included a...read more

 

Saltwater Fly Guide

I've chartered two trips with Captain Dave Yoder, fly fishing for tarpon, bonefish, permit, snook and other species. His guiding expertise covers the...read more

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DEAL!! Enchanted Tropical Cottage - Canal Front, Minutes To Ocean!
Islamorada House Rental Picture
  • House Rental Deals and Discounts 10% off = $1,575 per week
  • House Rental Deals and Specials 1 DOUBLE/4 SINGLE KAYAKS & 4 BICYCLES ($1000)
  • bedrooms 2
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,750 - $2,195 /wk
    $3,400 - $3,900 /mth
 
 
 
 
 

2 reviews write a review

DEAL!! Futura Yacht Club - All you need is your bathing suits!!
Islamorada Condo Rental Picture
  • Condo Rental Deals and Discounts $250 off = $600 per week
  • bedrooms 2
  • community Futura Yacht Club
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $600 - $850 /wk
    $2,200 - $3,200 /mth
 
 
 
 
 

19 reviews write a review

DEAL!! Islamorada Waterfront Paradise Getaway
Islamorada Studio Rental Picture
  • Studio Rental Deals and Discounts $300 off = $900 per week
  • bedrooms 0
  • community Lower Matecumbe
  • rental type Studio
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $900 - $2,100 /wk
    $4,000 - $6,000 /mth
 
 
 
 
 

47 reviews write a review

DEAL!! Keys Condo Luxurious Waterfront w/2 Master Bedrooms
Islamorada Condo Rental Picture
  • Condo Rental Deals and Discounts $200 off = $1,300 per week
  • Condo Rental Deals and Specials Welcome Gifts ($30)
  • bedrooms 2
  • community Bay Harbour
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1 /nt
    $1,400 - $2,000 /wk
 
 
 
 
 

43 reviews write a review

DEAL!! ~Keys Cottage~ Marathon Florida
Islamorada Studio Rental Picture
  • Studio Rental Deals and Discounts 10% off = $535 per week
  • bedrooms 1
  • community Coco Plum Terraces
  • rental type Studio
  • sleeps 3
  • baths 1
  • rates (USD) $90 - $140 /nt
    $595 - $895 /wk
    $1,900 - $2,800 /mth
 
 
 
 
 

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DEAL!! Plantation Key Paradise
Islamorada House Rental Picture
  • House Rental Deals and Discounts 20% off = $720 per week
  • House Rental Deals and Specials Fresh FL Keys Seafood ($100)
  • bedrooms 2
  • community Plantation Key Colony
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $750 - $1,000 /wk
    $1,500 - $3,000 /mth
 
 
 
 
 

2 reviews write a review

Oceanfront Condo with Panoramic Views
Islamorada Condo Rental Picture
  • bedrooms 2
  • community Sea Gulls Condos
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $800 - $1,250 /wk
 
 
 
 
 

2 reviews write a review

Islamorada Oceanfront Vacation Rental Home
Islamorada House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $3,800 - $4,800 /wk
    $11,400 - $14,400 /mth
 
 
 
 
 

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Secluded Oceanview Townhome
Islamorada Townhome Rental Picture
  • bedrooms 2
  • community
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $1,250 - $1,800 /wk
    $4,000 - $6,000 /mth
 
 
 
 
 

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Islamorada - Oceanfront private beach, heated pool & dockage
Islamorada House Rental Picture
  • bedrooms 4
  • community Islamorada South
  • rental type House
  • sleeps 8
  • baths 4
  • rates (USD) $4,800 - $5,200 /wk
 
 
 
 
 

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Serene Oceanside Keys Getaway
Islamorada House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $300 - $500 /nt
    $1,800 - $2,250 /wk
    $3,600 - $4,200 /mth
 
 
 
 
 

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Paradise House
Islamorada House Rental Picture
  • bedrooms 1
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $250 - $300 /nt
    $1,700 - $2,050 /wk
 
 
 
 
 

8 reviews write a review

++ ON SALE - Best Accomodation + Great Location
Islamorada House Rental Picture
  • bedrooms 2
  • community White Marlin Beach
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $875 /wk
    $2,500 /mth
 
 
 
 
 

3 reviews write a review

Islamorada Oceanfront Vacation Home- Casa Eroici
Islamorada House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $4,500 - $5,800 /wk
    $13,500 - $17,400 /mth
 
 
 
 
 

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**Ocean Front Jewel, Private Pool,Private 70FT Dock**
Islamorada House Rental Picture
  • bedrooms 4
  • community Ocean Estates
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 3
  • rates (USD) $350 - $500 /nt
    $2,450 - $3,000 /wk
    $8,500 - $9,800 /mth
 
 
 
 
 

3 reviews write a review

OceanfrontPeninsula Pool Dock water3sides 7nite min 6ppl max
Islamorada House Rental Picture
  • bedrooms 3
  • community Lower Matecumbe
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $425 - $500 /nt
    $2,975 - $3,500 /wk
    $8,925 - $10,500 /mth
 
 
 
 
 

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********Pool, Ocean Front, Beach @ The Beach House****
Islamorada House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $2,500 - $3,500 /wk
 
 
 
 
 

4 reviews write a review

***Pool, Dock, Gated, Bay, Luxury @ Pineapple Plantation****
Islamorada House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $21,000 /mth
 
 
 
 
 

2 reviews write a review

Seagulls Oceanfront Condo on Atlantic Ocean
Islamorada Condo Rental Picture
  • bedrooms 1
  • community Sea Gulls Condos
  • rental type Condo
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $700 - $900 /wk
    $1,600 - $3,400 /mth
 
 
 
 
 

12 reviews write a review

Casa Linda Vacation Home with Concrete Dock
Islamorada House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,000 - $1,300 /wk
    $3,000 - $3,900 /mth
 
 
 
 
 

8 reviews write a review

Beautiful Vacation Home in Lower Matecumbe
Islamorada House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $3,800 - $4,500 /mth
 
 
 
 
 

4 reviews write a review

Tropical Paradise at Futura Yacht Club
Islamorada Condo Rental Picture
  • bedrooms 2
  • community Futura Yacht Club
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $600 - $850 /wk
 
 
 
 
 

5 reviews write a review

Holzman's Bayside; condo on Florida Bay
Islamorada Condo Rental Picture
  • bedrooms 1
  • community Holiday House
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,295 - $1,495 /wk
    $5,000 - $5,700 /mth
 
 
 
 
 

26 reviews write a review

Keys Kottage A villa in secluded hammock on Florida Bay
Islamorada Villa Rental Picture
  • bedrooms 2
  • community Holiday House
  • rental type Villa
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,295 - $1,495 /wk
    $5,000 - $5,700 /mth
 
 
 
 
 

29 reviews write a review

Paradise Made Easy! Getaway at Summer Sea in Islamorada!
Islamorada Condo Rental Picture
  • bedrooms 1
  • community Summer Sea Condos
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $700 - $850 /wk
 
 
 
 
 

4 reviews write a review

Paradise Found - Oceanside with Pool
Islamorada House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,800 - $2,500 /wk
    $5,000 - $6,000 /mth
 
 
 
 
 

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Keys Villa. Private Secluded House on the Bay.
Islamorada House Rental Picture
  • bedrooms 2
  • community Holiday House
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $895 - $1,095 /wk
 
 
 
 
 

67 reviews write a review

Mitchell's Bay View Villa - Islamorada House on the Bay
Islamorada Villa Rental Picture
  • bedrooms 2
  • community Holiday House
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,295 - $1,495 /wk
 
 
 
 
 

58 reviews write a review

Great Islamorada Location at Good Price with Free WiFi
Islamorada Townhome Rental Picture
  • bedrooms 2
  • community Executive Bay Club
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $190 - $230 /nt
    $1,200 - $1,650 /wk
    $3,200 - $4,200 /mth
 
 
 
 
 

12 reviews write a review

Oceanfront condo Plantation Key screened porch and internet
Islamorada Condo Rental Picture
  • bedrooms 2
  • community Sea Gulls Condos
  • rental type Condo
  • sleeps 5
  • baths 2
  • rates (USD) $875 - $1,500 /wk
    $3,000 - $4,400 /mth
 
 
 
 
 

18 reviews write a review

Waterfront Condo - Paradise in the Florida Keys
Islamorada Condo Rental Picture
  • bedrooms 1
  • community Summer Sea Condos
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $895 - $1,195 /wk
    $2,995 - $3,495 /mth
 
 
 
 
 

12 reviews write a review

Breath of Salty Air
Islamorada Condo Rental Picture
  • bedrooms 2
  • community Sea Gulls Condos
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $850 - $1,400 /wk
    $2,500 - $4,300 /mth
 
 
 
 
 

1 reviews write a review

Deep Water Canalfront Home W/ Boat Ramp
Islamorada House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,300 - $1,500 /wk
    $3,400 - $3,900 /mth
 
 
 
 
 

5 reviews write a review

"ARTE" Paradise lost
Islamorada House Rental Picture
  • bedrooms 3
  • community Plantation Key Colony
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $2,999 - $3,999 /mth
 
 
 
 
 

11 reviews write a review

Fisherman's Dream- Canal Home- Plantation Key- Islamorada
Islamorada House Rental Picture
  • bedrooms 3
  • community Plantation Key Colony
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $1,500 - $2,200 /wk
    $2,200 - $3,800 /mth
 
 
 
 
 

1 reviews write a review

The Great Islamorada Getaway
Islamorada House Rental Picture
  • bedrooms 4
  • community Indian Mound
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 3
  • rates (USD) $2,700 - $3,200 /wk
    $7,900 - $8,500 /mth
 
 
 
 
 

15 reviews write a review

Beautiful townhome in a tropical setting
Islamorada Townhome Rental Picture
  • bedrooms 2
  • community Executive Bay Club
  • rental type Townhome
  • sleeps 6
  • baths 2
  • rates (USD) $165 - $195 /nt
    $1,050 - $1,250 /wk
    $2,600 - $3,400 /mth
 
 
 
 
 

1 reviews write a review

"Islamorada / Townhouse with 25ft Boat Dockage"
Islamorada Townhome Rental Picture
  • bedrooms 2
  • community Islamorada South
  • rental type Townhome
  • sleeps 6
  • baths 2
  • rates (USD) $1,500 /wk
    $2,500 - $3,000 /mth
 
 
 
 
 

1 reviews write a review

Beautiful Bay Harbour Condo! Book your Fall vacation now!
Islamorada Condo Rental Picture
  • bedrooms 3
  • community Bay Harbour
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $1,800 - $2,500 /wk
    $4,000 - $5,500 /mth
 
 
 
 
 

11 reviews write a review

" The White Marlin Beach House "
Islamorada House Rental Picture
  • bedrooms 2
  • community Islamorada South
  • rental type House
  • sleeps 5
  • baths 2
  • rates (USD) $1,500 - $1,700 /wk
    $4,500 - $6,000 /mth
 
 
 
 
 

1 reviews write a review

Chillax Keys Style
Islamorada House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $2,500 /wk
    $7,000 - $8,000 /mth
 
 
 
 
 

6 reviews write a review

*******Ocean Front, Pool, Dockage @ Aguazul*******
Islamorada House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $4,500 /wk
 
 
 
 
 

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****** Ocean Front, Pool, Newer @ Latitude*********
Islamorada House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $18,000 - $20,000 /mth
 
 
 
 
 

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****Ocean front, Pool, Dock @ Oasis****
Islamorada House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $12,000 - $16,000 /mth
 
 
 
 
 

2 reviews write a review

***Pool, Beach, Tennis, Gated Private Estate @ Kara-Pan*
Islamorada House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 10
  • baths 6
  • rates (USD) $8,950 /wk
 
 
 
 
 

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*Ocean Front, Pool, Private 3 Acres @ Southern Comfort****
Islamorada House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $5,000 - $6,000 /wk
    $18,000 - $24,000 /mth
 
 
 
 
 

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****Oceanfront, Dock, Pool @ The Gardens*****
Islamorada House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 8
  • baths 4
  • rates (USD) $6,000 - $6,500 /wk
    $19,500 - $26,000 /mth
 
 
 
 
 

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*****Oceanfront, Boat Basin @ Blue Harbor******
Islamorada House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $2,500 - $3,000 /wk
    $10,000 - $12,000 /mth
 
 
 
 
 

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***Relax and Rejuvenate*** @ "The Palms"
Islamorada House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $5,000 - $6,000 /wk
    $15,000 - $24,000 /mth
 
 
 
 
 

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***Ocean Front, Beach, Pool" @ "Turtle Nest"
Islamorada House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $5,000 - $6,000 /wk
 
 
 
 
 

1 reviews write a review

Oceanfront Private Home On Sandy Beach
Islamorada House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $2,500 - $3,000 /wk
    $6,500 - $7,000 /mth
 
 
 
 
 

3 reviews write a review

3BR/3BA Beautiful Waterfront Home Monthly Rental
Islamorada House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $6,000 /mth
 
 
 
 
 

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Boaters Paradise in the Keys
Islamorada House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $2,000 - $2,500 /mth
 
 
 
 
 

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Executive Bay Club - Endless Paradise
Islamorada Townhome Rental Picture
  • bedrooms 3
  • community Executive Bay Club
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $2,400 - $3,000 /mth
 
 
 
 
 

10 reviews write a review

Sunny Haven
Islamorada House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $700 /nt
    $3,000 /wk
    $8,000 /mth
 
 
 
 
 

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Tropical paradise in Islamorada
Islamorada Townhome Rental Picture
  • bedrooms 2
  • community Islamorada South
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $2,000 - $3,000 /mth
 
 
 
 
 

3 reviews write a review

Islamorada - Beacon Reef Condo with up to 30' boat dock!
Islamorada Condo Rental Picture
  • bedrooms 2
  • community Lower Matecumbe
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $3,700 - $4,550 /mth
 
 
 
 
 

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Beautiful Oceanfront Condo
Islamorada Condo Rental Picture
  • bedrooms 2
  • community Sea Gulls Condos
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $900 - $1,595 /wk
 
 
 
 
 

4 reviews write a review

Summer Sea
Islamorada Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 5
  • baths
  • rates (USD) $575 - $850 /wk
 
 
 
 
 

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Sea Gulls Condominiums, Ocean, Pool, King bed
Islamorada Condo Rental Picture
  • bedrooms 1
  • community Sea Gulls Condos
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $700 - $950 /wk
 
 
 
 
 

16 reviews write a review

Islamorada Villa
Islamorada House Rental Picture
  • bedrooms 4
  • community Venetian Shores
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $3,300 /wk
    $9,000 /mth
 
 
 
 
 

1 reviews write a review

Keys Condo
Islamorada Condo Rental Picture
  • bedrooms 3
  • community Bay Harbour
  • rental type Condo
  • sleeps 8
  • baths
  • rates (USD) $6,000 - $8,200 /mth
 
 
 
 
 

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Islamorada, Canal Front, Beautiful 4BR 4BA Pool Home
Islamorada House Rental Picture
  • bedrooms 4
  • community Venetian Shores
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $6,000 /mth
 
 
 
 
 

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Bayfront Islamorada
Islamorada House Rental Picture
  • bedrooms 6
  • community High Point
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $7,500 - $10,000 /mth
 
 
 
 
 

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The Falcon Estate
Islamorada House Rental Picture
  • bedrooms 6
  • community
  • rental type House
  • sleeps 14
  • baths 6
  • rates (USD) $5,500 - $8,500 /wk
    $20,000 - $24,000 /mth
 
 
 
 
 

1 reviews write a review

Islamorada Waterfront Beauty-Available Now
Islamorada House Rental Picture
  • bedrooms 3
  • community Islamorada South
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $1 /nt
    $1 /wk
    $3,000 - $5,000 /mth
 
 
 
 
 

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Sandy Cove Condo
Islamorada Condo Rental Picture
  • bedrooms 1
  • community Matecumbe Sandy Cove
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $800 /wk
    $2,500 /mth
 
 
 
 
 

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Serenity And Zen Await You
Islamorada Apartment Rental Picture
  • bedrooms 1
  • community Port Antigua
  • rental type Apartment
  • sleeps 2
  • baths 1
  • rates (USD) $1,800 /mth
 
 
 
 
 

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Cocomo's
Islamorada House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 4
  • rates (USD) $6,000 /wk
    $19,000 /mth
 
 
 
 
 

6 reviews write a review

Sunsets at Islamorada, Florida Keys. 2/2 Townho
Islamorada Townhome Rental Picture
  • bedrooms 2
  • community Executive Bay Club
  • rental type Townhome
  • sleeps 6
  • baths 2
  • rates (USD) $2,400 - $2,800 /mth
 
 
 
 
 

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Seaside Sanctuary 5bd/5bth Pool Home
Islamorada House Rental Picture
  • bedrooms 5
  • community Plantation Key
  • rental type House
  • sleeps 14
  • baths 5
  • rates (USD) $4,000 - $6,500 /wk
 
 
 
 
 

2 reviews write a review

Bay Harbour
Islamorada Condo Rental Picture
  • bedrooms 3
  • community
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $3,000 - $4,000 /wk
    $5,000 - $10,000 /mth
 
 
 
 
 

2 reviews write a review

Windley Key, FL Keys
Islamorada Mobile home Rental Picture
  • bedrooms 1
  • community Windley Key Mobile Home Park
  • rental type Mobile home
  • sleeps 4
  • baths 1
  • rates (USD) $1,800 /mth
 
 
 
 
 

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Exquisite Port Antigua Waterfront Home with Sandy Beach
Islamorada House Rental Picture
  • bedrooms 3
  • community Port Antigua
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $2,500 - $3,000 /mth
 
 
 
 
 

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Summer Sea Condominium
Islamorada Studio Rental Picture
  • bedrooms 0
  • community Summer Sea Condos
  • rental type Studio
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $450 - $700 /wk
 
 
 
 
 

40 reviews write a review

Mi Casa Su Casa
Islamorada Townhome Rental Picture
  • bedrooms 2
  • community Executive Bay Club
  • rental type Townhome
  • sleeps 6
  • baths 2
  • rates (USD) $1,500 /wk
    $2,750 /mth
 
 
 
 
 

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Islander Bayside- pool, boat slips,
Islamorada Townhome Rental Picture
  • bedrooms 2
  • community Islamorada/Tavernier
  • rental type Townhome
  • sleeps 4
  • baths
  • rates (USD) $239 - $609 /nt
    $1,275 - $2,745 /wk
    $3,200 - $8,500 /mth
 
 
 
 
 

1 reviews write a review

vacation home Islamorada,fl
Islamorada House Rental Picture
  • bedrooms 3
  • community Venetian Shores
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $4,350 - $4,500 /mth
 
 
 
 
 

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Florida Keys Waterfront Home
Islamorada House Rental Picture
  • bedrooms 2
  • community Tavernier
  • rental type House
  • sleeps 9
  • baths 2
  • rates (USD) $2,000 - $4,500 /mth
 
 
 
 
 

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Canal Front Home with Pool and Dock
Islamorada House Rental Picture
  • bedrooms 4
  • community Venetian Shores
  • rental type House
  • sleeps 1
  • baths 4
  • rates (USD) $3,500 - $4,500 /wk
    $13,000 - $17,000 /mth
 
 
 
 
 

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Tropical Paradise located in Venetian Shores
no photo available
  • bedrooms 6
  • community Venetian Shores
  • rental type House
  • sleeps 13
  • baths
  • rates (USD) $3,500 - $4,500 /wk
    $6,500 - $8,500 /mth
 
 
 
 
 

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Ocean side Lower Matecumbe
Islamorada House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $2,700 /mth
 
 
 
 
 

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Beautiful Ocean & Bay at Sandy Cove w/ up to 30" Boat Slip
Islamorada Condo Rental Picture
  • bedrooms 3
  • community Sandy Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,650 - $1,800 /wk
 
 
 
 
 

2 reviews write a review

Boater's Delight/Fishing Paradise
Islamorada House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $1,500 - $7,500 /mth
 
 
 
 
 

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Oceanfront 2BR/2BA Condo in Paradise
Islamorada Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $900 - $1,300 /wk
 
 
 
 
 

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Doug's Backwater Flat on Florida Bay w/marina
Islamorada Condo Rental Picture
  • bedrooms 1
  • community
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $595 - $695 /wk
    $1,750 - $1,850 /mth
 
 
 
 
 

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Futura condo Pool, Dockage, Sunsets, Dockage
Islamorada Condo Rental Picture
  • bedrooms 2
  • community Futura Yacht Club
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $825 - $1,225 /wk
    $3,000 - $4,000 /mth
 
 
 
 
 

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3/2 condo Futura Yacht Club Pool, Dockage, Wifi
Islamorada Condo Rental Picture
  • bedrooms 3
  • community Futura Yacht Club
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,125 - $1,525 /wk
    $3,600 - $5,000 /mth
 
 
 
 
 

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Islamorada home great boating deep water basin
Islamorada House Rental Picture
  • bedrooms 3
  • community Treasure Harbor
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,800 - $2,200 /wk
    $3,800 - $4,500 /mth
 
 
 
 
 

1 reviews write a review

Waterfront Townhouse Futura, Pool, Dockage
Islamorada Townhome Rental Picture
  • bedrooms 2
  • community Futura Yacht Club
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $1,125 - $1,525 /wk
    $4,000 - $5,000 /mth
 
 
 
 
 

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Villa Marlin, renovated and remodeled, private sandy beach
Islamorada House Rental Picture
  • bedrooms 3
  • community White Marlin Beach
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $2,700 - $2,900 /wk
 
 
 
 
 

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The PERFECT getaway with brand new HEATED swimming pool
Islamorada House Rental Picture
  • bedrooms 4
  • community Venetian Shores
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $2,500 - $3,500 /wk
    $5,000 - $8,000 /mth
 
 
 
 
 

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Islamorada Paradise on the Bay (Futura Yacht Club)
Islamorada Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $700 - $1,500 /wk
    $2,800 - $4,000 /mth
 
 
 
 
 

1 reviews write a review

Luxurious 6bed/5bath Canal Front Home with Elevator & Heated Pool
Islamorada House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 12
  • baths 5
  • rates (USD) $5,300 - $6,200 /wk
 
 
 
 
 

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Oceanfront End Unit, Pool, WiFi, Tennis, Great Ocean Views!
Islamorada Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $110 - $225 /nt
    $800 - $1,575 /wk
 
 
 
 
 

11 reviews write a review

Cozy Keys Getaway- Great Dockage- Wifi-Clean & Open-
Islamorada House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD)
 
 
 
 
 

12 reviews write a review

Islamorada Waterfront-Great Dockage! Wonderful Views! WiFi & More!
Islamorada House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD)
 
 
 
 
 

8 reviews write a review

Oceanfront Estate the Keys Largest and Most Prestigious Home
Islamorada Estate Rental Picture
  • bedrooms 8
  • rental type Estate
  • sleeps 20
  • baths
  • rates (USD) $500 - $1,143 /nt
    $14,000 /mth
 
 
 
 
 

2 reviews write a review

Bayfront with Free Dockage and Outstanding View!
Islamorada Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD)
 
 
 
 
 

8 reviews write a review

27 steps to Paradise Bay
Islamorada Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $129 - $200 /nt
    $3,000 - $3,900 /mth
 
 
 
 
 

16 reviews write a review

Islamorada Oceanfront Estate 2 Lush Acres with Dockage Private
Islamorada House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD)
 
 
 
 
 

3 reviews write a review

Florida Keys Townhouse in Executive Bay **LABOR DAY PROMO**
Islamorada Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $2,772 - $5,460 /mth
 
 
 
 
 

5 reviews write a review

Ocean Harbour- It Has It All For Your Keys Adventure Monthly Rental
Islamorada Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 8
  • baths
  • rates (USD) $6,800 /mth
 
 
 
 
 

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A Beauty on Two Converging Crystal Clear Canals
Islamorada House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 3
  • rates (USD) $2,300 /wk
    $6,900 /mth
 
 
 
 
 

12 reviews write a review

Clean, Classic Florida Keys Style On A Budget
Islamorada Studio Rental Picture
  • bedrooms 0
  • rental type Studio
  • sleeps 2
  • baths 1
  • rates (USD) $550 - $600 /wk
    $2,200 - $2,400 /mth
 
 
 
 
 

4 reviews write a review

Oceanfront Anglers Reef, Islamorada, Florida Keys, Video Tour
Islamorada House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,495 - $1,895 /wk
    $4,995 - $7,495 /mth
 
 
 
 
 

14 reviews write a review

TROPICAL PARADISE AT EXECUTIVE BAY CLUB
Islamorada Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $1,250 - $2,000 /wk
    $3,250 - $4,000 /mth
 
 
 
 
 

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Fabulous View, Split 2/2 Up, 2/1 Down, Ideal for 2 Families
Islamorada House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $5,133 - $6,067 /mth
 
 
 
 
 

6 reviews write a review

Dream Home in the Keys with Heated Pool Legal Weekly Rental
Islamorada House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 3
  • rates (USD) $2,750 - $4,500 /wk
 
 
 
 
 

10 reviews write a review

Spectacular Top Floor Oceanfront View Condo
Islamorada Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD)
 
 
 
 
 

31 reviews write a review

Keys home in Anglers Reef with ocean view, dock, community pool & private beach
Islamorada House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $2,250 - $2,600 /wk
 
 
 
 
 

31 reviews write a review

Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi
Islamorada House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $2,500 /wk
 
 
 
 
 

1 reviews write a review

Islamorada Bay Front Condo With 36ft Deep Water Boat Slip
Islamorada Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,150 - $1,500 /wk
    $4,500 /mth
 
 
 
 
 

1 reviews write a review

Gorgeous Oceanfront with heated pool, 350' pier, free wifi
Islamorada House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $2,600 - $3,200 /wk
 
 
 
 
 

24 reviews write a review

Paradise Made Easy In Isamorada!
Islamorada Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $750 - $850 /wk
 
 
 
 
 

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Angler's Reef Coastal Conch Style Vacation Home in Islamorada, Fl.
Islamorada House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $215 /nt
    $1,500 /wk
    $4,950 /mth
 
 
 
 
 

25 reviews write a review

Oceanview Luxury Townhome
Islamorada Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $2,500 - $3,000 /wk
 
 
 
 
 

5 reviews write a review

Secluded Ocean Front Cottages & Private Beach & 230' Dock in Islamorada, FL
Islamorada Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $2,480 /wk
 
 
 
 
 

6 reviews write a review

Luxury Keys Home In Paradise - 106 Angler's Reef In Beautiful Islamorada
Islamorada Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 6
  • baths
  • rates (USD) $1,650 - $2,400 /wk
    $4,000 - $6,000 /mth
 
 
 
 
 

7 reviews write a review

Keys home in Anglers Reef with ocean view, dock, comm. pool & beach
Islamorada House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,700 - $2,400 /wk
 
 
 
 
 

26 reviews write a review

Beautiful Single Family Home In Gated Community, Beautiful Grounds, Must See
Islamorada House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $1,500 - $1,900 /wk
    $4,500 - $5,800 /mth
 
 
 
 
 

1 reviews write a review

Paradise In The Florida Keys sleep 6 (or 12). One month minimum stay.
Islamorada House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $3,500 - $4,200 /wk
    $9,995 - $16,800 /mth
 
 
 
 
 

1 reviews write a review

Welcome to Paradise!
Islamorada Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

6 reviews write a review

The Markeysa, the Ultimate Keys Experience - Private Beach
Islamorada House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 4
  • rates (USD) $6,500 - $7,500 /wk
 
 
 
 
 

18 reviews write a review

CONCH HOUSE - INCLUDES BOAT HARBOR & FISHING PIER
Islamorada House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $263 /nt
 
 
 
 
 

1 reviews write a review

Bigger Than You Think - This is Your Next Rental!
Islamorada House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $3,733 - $4,600 /mth
 
 
 
 
 

1 reviews write a review

Water Front 3/3 Family and Boat Friendly Home, Great Views
Islamorada House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $4,667 /mth
 
 
 
 
 

3 reviews write a review

Paradise Oceanview Townhome
Islamorada Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 4
  • baths
  • rates (USD) $1,300 - $1,800 /wk
 
 
 
 
 

2 reviews write a review

Southern Diversion Estate - Islamorada Great Wedding Venue
Islamorada House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 16
  • baths
  • rates (USD) $7,800 - $9,800 /wk
 
 
 
 
 

4 reviews write a review

Luxury Florida Keys Estate
Islamorada Estate Rental Picture
  • bedrooms 3
  • rental type Estate
  • sleeps 8
  • baths 3
  • rates (USD) $12,600 /mth
 
 
 
 
 

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La Siesta Resort And Marina, An All Suites Hotel - Resort View One Bedroom Suite
Islamorada Hotel Rental Picture
  • bedrooms 1
  • rental type Hotel
  • sleeps 2
  • baths 1
  • rates (USD) $209 - $1,000 /nt
 
 
 
 
 

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La Siesta Resort And Marina, An All Suites Hotel - Ocean Pool View 1BR Suite
Islamorada Hotel Rental Picture
  • bedrooms 1
  • rental type Hotel
  • sleeps 3
  • baths 1
  • rates (USD) $229 - $1,150 /nt
 
 
 
 
 

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Little Palm Home - Enjoy Boat Harbor & Fishing Pier
Islamorada House Rental Picture
  • bedrooms 1
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $197 /nt
 
 
 
 
 

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Beautiful 3/2 on 450’ of Waterfront W/ Tropical Pool and 4 Tiki Huts
Islamorada House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD)
 
 
 
 
 

2 reviews write a review

Beautifl lush garden home located in the 'Heart of Islamorada'
Islamorada Estate Rental Picture
  • bedrooms 4
  • rental type Estate
  • sleeps 10
  • baths 4
  • rates (USD) $5,500 /wk
 
 
 
 
 

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"Islamorada Sol" Beautiful Home with Dock & Beach
Islamorada House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD)
 
 
 
 
 

2 reviews write a review

Islamorada Beachfront Apartment - Spectacular Sunsets!
Islamorada Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD)
 
 
 
 
 

37 reviews write a review

Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier.
Islamorada Lodge Rental Picture
  • bedrooms 2
  • rental type Lodge
  • sleeps 8
  • baths 2
  • rates (USD)
 
 
 
 
 

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Islander Bayside- New Luxury Bayfront Townhomes - Two Bedrooms, Boating, Fishing
Islamorada Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 5
  • baths
  • rates (USD)
 
 
 
 
 

1 reviews write a review

Luxurious Bay Harbour - Ocean View, Boat Dock, Pool, Jacuzzi & Tennis Courts!
Islamorada Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD)
 
 
 
 
 

5 reviews write a review

Beachfront in Paradise
Islamorada House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD)
 
 
 
 
 

1 reviews write a review

Boater's/Fisherman's Delight in Paradise
Islamorada House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD)
 
 
 
 
 

5 reviews write a review