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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Apartment in Islamorada
Luxury condo with boat slip overlooking the bay
3 bedrooms, 3 beds, 2.5 private bathrooms
18–25 Aug
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5.0 out of 5 average rating, 36 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed
19–24 Aug
4.93 out of 5 average rating, 389 reviews
Guest favourite
Houseboat in Marathon
b watervibe
1 bedroom, 1 small double bed
27 Sept – 2 Oct
4.92 out of 5 average rating, 92 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
29 Aug – 5 Sept
4.97 out of 5 average rating, 219 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
20–25 Aug
New place to stay
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds
24–29 Aug
5.0 out of 5 average rating, 4 reviews
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed
19–24 Aug
4.92 out of 5 average rating, 37 reviews
Featured hotel
Room in Key Largo
Waterfront suite 9
23–28 Aug
Top guest favourite
Flat in Islamorada
Sunset Access + Boat Basin | Walkable Islamorada
2 bedrooms, 2 beds
24–29 Aug
4.97 out of 5 average rating, 96 reviews
Guest favourite
Home in Key Largo
Your Keys Getaway!
2 bedrooms, 2 queen beds
30 Aug – 4 Sept
4.9 out of 5 average rating, 461 reviews
Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds
9–14 Oct
5.0 out of 5 average rating, 91 reviews
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed
23–28 Aug
4.8 out of 5 average rating, 51 reviews
Guest favourite
Townhouse in Islamorada
Bayside Townhome in Islamorada with Boat Slip
2 bedrooms, 4 beds
22–29 Aug
4.98 out of 5 average rating, 91 reviews
Superhost
Villa in Islamorada
Sirens Cove - Game Room, Pool - Dock Access
3 bedrooms, 5 beds
19–26 Aug
New place to stay
Cottage in Islamorada
The Flagler, Floating Villa, 2 Bedroom, Full Bath
2 bedrooms, 1 bed
18–23 Aug
Top guest favourite
Guest suite in Tavernier
Key Largo! Tavernier! Welcome to Paradise!
1 bedroom, 1 king bed
31 Aug – 5 Sept
4.98 out of 5 average rating, 349 reviews
Guest favourite
Apartment in Tavernier
Condo in Tavernier
2 bedrooms, 3 beds
20–25 Aug
4.96 out of 5 average rating, 51 reviews
Guest favourite
Houseboat in Islamorada Tavernier
Baycation Houseboat | Florida Keys Waterfront Stay
1 bedroom, 2 beds
24–29 Aug
4.9 out of 5 average rating, 275 reviews
Top guest favourite
Boat in Tavernier
Island Sanctuary Islamorada
2 bedrooms, 2 beds
18–23 Aug
4.92 out of 5 average rating, 401 reviews