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Search results; Over 1,000 homes in Key West

Guest favourite
Apartment in Key West
Condo de Paradise/Salt Water Pool/Boat Dock
2 bedrooms, 3 beds, 2 private bathrooms
18–25 Jul
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4.96 out of 5 average rating, 45 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
4.91 out of 5 average rating, 554 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
New place to stay, 1 bedroom, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5.0 out of 5 average rating, 38 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
Luxe
Home in Key West
Spindrift House at Lunara Bay
4.85 out of 5 average rating, 95 reviews, 4 bedrooms, 7 beds, 4 bathrooms
14–19 Aug
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 4 beds, 2 bathrooms
10–17 Aug
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
5.0 out of 5 average rating, 12 reviews, 4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 2 bathrooms
6–11 Aug
Hotel in Key West
Tropical King
New place to stay, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Superhost
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
2 bedrooms, 2 beds, 2 bathrooms
20–25 Jul
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
4.83 out of 5 average rating, 111 reviews, 5 bedrooms, 6 beds, 3 bathrooms
27 Aug – 1 Sept
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4.56 out of 5 average rating, 25 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
Guest favourite
Houseboat in Key West
Tiki Suites~The Grand Tiki~Private Water Stay
4.92 out of 5 average rating, 356 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Jul
Top guest favourite
Holiday home in Key Colony Beach
Waterfront 4BR | Dual Living | Hot Tub | Dock
5.0 out of 5 average rating, 27 reviews, 4 bedrooms, 4 beds, 3 bathrooms
22–27 Aug
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4.83 out of 5 average rating, 23 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
17–22 Jul
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
8–13 Aug
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
5.0 out of 5 average rating, 26 reviews, 6 bedrooms, 6 beds, 6.5 bathrooms
2–7 Aug
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 97 reviews, 3 bedrooms, 3 beds, 4 bathrooms
22–27 Aug