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Search results; Over 1,000 homes in Key West

Houseboat in Key West
Happys Houseboat
1 bedroom, 1 bed, 1 private bathroom
6–11 Aug
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4.79 out of 5 average rating, 272 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
6–11 Aug
4.91 out of 5 average rating, 557 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
22–29 Aug
5.0 out of 5 average rating, 86 reviews
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
4.91 out of 5 average rating, 101 reviews
Superhost
Home in Key West
Fleming Street 2/1 private home Key West getaway
2 bedrooms, 4 beds, 1 bathroom
14–19 Aug
4.91 out of 5 average rating, 135 reviews
Luxe
Home in Key West
Catchlight House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 38 reviews
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 6 reviews
Flat in Key West
Apartment in Key west
1 bedroom, 1 queen bed, 1 bathroom
8–13 Aug
New place to stay
Home in Marathon
Keys Coastal Getaway | King + 2Q | 10 Min Sombrero
2 bedrooms, 3 beds, 2 bathrooms
3–10 Aug
New place to stay
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 38 reviews
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
3–8 Aug
4.86 out of 5 average rating, 42 reviews
Superhost
Home in Key West
Mango Cottage, a charming Key West home ready for
3 bedrooms, 4 beds, 2 bathrooms
27 Aug – 1 Sept
4.91 out of 5 average rating, 130 reviews
Guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Key West
Pilar's Secret - walking distance to everything!
3 bedrooms, 5 beds, 2 bathrooms
21–26 Aug
4.92 out of 5 average rating, 88 reviews
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Away Awai Floating Vill
2 bedrooms, 2 queen beds, 2 bathrooms
4–9 Aug
4.93 out of 5 average rating, 84 reviews
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds, 3 bathrooms
18–23 Aug
New place to stay
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Apartment in Key West
Coastline Comfort
2 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 7 reviews