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Search results; Over 1,000 homes in Key West

Houseboat in Key West
Key West Luxury Houseboat at Yacht Club Resort
2 bedrooms, 3 beds, 2.5 private bathrooms
17–22 Jul
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4.8 out of 5 average rating, 296 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
23–28 Sept
New place to stay
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
4.91 out of 5 average rating, 554 reviews
Featured hotel
Hotel in Key West
Pool view one king bed accessible
1 bedroom, 1 bathroom
15–20 Jul
New place to stay
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
6–11 Aug
5.0 out of 5 average rating, 4 reviews
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
Superhost
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
2 bedrooms, 2 queen beds, 2 bathrooms
20–25 Jul
Luxe
Home in Key West
Spindrift House at Lunara Bay
4 bedrooms, 7 beds, 4 bathrooms
14–19 Aug
4.85 out of 5 average rating, 95 reviews
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
27 Aug – 1 Sept
4.83 out of 5 average rating, 111 reviews
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
2 bedrooms, 4 beds, 2 bathrooms
10–17 Aug
5.0 out of 5 average rating, 9 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
4.56 out of 5 average rating, 25 reviews
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, 12 reviews
Hotel in Key West
Tropical King
1 bedroom, 1 bed, 1 bathroom
19–24 Jul
New place to stay
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds, 4.5 bathrooms
17–22 Jul
4.83 out of 5 average rating, 23 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.97 out of 5 average rating, 201 reviews
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, 3 reviews
Luxe
Home in Key West
The Greenmoor House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 10 reviews
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
6 bedrooms, 6 beds, 6.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 27 reviews
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
2 bedrooms, 4 beds, 2.5 bathrooms
8–13 Aug
5.0 out of 5 average rating, 3 reviews