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Search results; Over 1,000 homes in Islamorada

Cottage in Islamorada
1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
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4.78 out of 5 average rating, 172 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
20–25 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
19–26 Aug
New place to stay
Top guest favourite
Houseboat in Marathon
b watervibe
1 bedroom, 1 small double bed, 1 bathroom
27 Sept – 2 Oct
4.92 out of 5 average rating, 93 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, 78 reviews
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed, 1 bathroom
21–26 Aug
4.92 out of 5 average rating, 37 reviews
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, 138 reviews
Guest favourite
Guest house in Key Largo
Romantic Bayside Guesthouse peaceful beach sunsets
1 bedroom, 1 queen bed, 1 bathroom
25–30 Aug
4.85 out of 5 average rating, 517 reviews
Top guest favourite
Flat in Islamorada
Sunset Access + Boat Basin | Walkable Islamorada
2 bedrooms, 2 beds, 2 bathrooms
24–29 Aug
4.97 out of 5 average rating, 96 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
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
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
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
Featured hotel
Room in Key Largo
Dolphin suite
2 double beds, 1 bathroom
23–28 Aug
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
20–25 Aug
4.93 out of 5 average rating, 249 reviews