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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
20–27 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, 1 bathroom
21–26 Aug
4.93 out of 5 average rating, 391 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
29 Aug – 5 Sept
4.97 out of 5 average rating, 219 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
23–28 Aug
4.8 out of 5 average rating, 5 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
20–25 Aug
New place to stay
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
20–27 Aug
New place to stay
Guest favourite
Camper van/Motorhome in Key Largo
RV by the Sea - Glamping in the Keys
2 bedrooms, 7 beds, 1 bathroom
23–28 Aug
4.88 out of 5 average rating, 139 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
4.96 out of 5 average rating, 79 reviews
Top guest favourite
Houseboat in Marathon
b watervibe
1 bedroom, 1 small double bed, 1 bathroom
21–26 Aug
4.92 out of 5 average rating, 93 reviews
Guest favourite
Houseboat in Islamorada Tavernier
Baycation Houseboat | Florida Keys Waterfront Stay
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.9 out of 5 average rating, 275 reviews
Featured hotel
Room in Key Largo
Cottage 6
2 queen beds, 1 bathroom
23–28 Aug
4.75 out of 5 average rating, 4 reviews
Guest favourite
Cottage in Key Largo
Kampground Paradise w/Kayaks, Heated Pool & Marina
2 bedrooms, 3 beds, 1 bathroom
31 Aug – 5 Sept
4.99 out of 5 average rating, 75 reviews
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 37 reviews
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
22–27 Aug
4.8 out of 5 average rating, 51 reviews
Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds, 2 bathrooms
9–14 Oct
5.0 out of 5 average rating, 92 reviews
Top guest favourite
Apartment in Tavernier
Tequila Sunrise
2 bedrooms, 2 beds, 2 bathrooms
30 Aug – 4 Sept
4.99 out of 5 average rating, 110 reviews
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
22–29 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Marathon
Oceanfront Tiny Villa in the Heart of the FL Keys
2 bedrooms, 2 beds, 1.5 bathrooms
21–26 Aug
4.93 out of 5 average rating, 249 reviews
Top guest favourite
Boat in Tavernier
Island Sanctuary Islamorada
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 401 reviews