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Search results; Over 1,000 homes in Key West

Guest favorite
Houseboat in Key West
Off-grid floating cottage on backcountry waters
2 bedrooms, 2 beds, 1 shared bath
Aug 12 – 17
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4.95 out of 5 average rating, 83 reviews
Guest favorite
Houseboat in Key West
Off-grid floating bungalow in Key West
4.91 out of 5 average rating, 557 reviews, 1 bedroom, 1 bed, 1 bath
Aug 18 – 23
Top guest favorite
Condo in Key West
Waterfront with a pool and boat slip
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 2 baths
Aug 23 – 28
Superhost
Home in Marathon
Oceanfront with a pool and private dock
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 4 beds, 3.5 baths
Aug 29 – Sep 5
Superhost
Home in Key West
Historic conch house with heated saltwater pool
4.91 out of 5 average rating, 130 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 27 – Sep 1
Featured hotel
Room in Key West
Pool view one king bed accessible
New place to stay, 1 bath
Aug 19 – 24
Top guest favorite
Home in Marathon
100-foot dock, heated pool, and spa
5.0 out of 5 average rating, 31 reviews, 6 bedrooms, 10 beds, 5 baths
Oct 3 – 10
Guest favorite
Home in Cudjoe Key
Waterfront home with a private dock
4.86 out of 5 average rating, 7 reviews, 2 bedrooms, 4 beds, 2 baths
Aug 24 – 29
Superhost
Home in Key West
Gated Coral Hammock with resort-style pool
New place to stay, 3 bedrooms, 6 beds, 3 baths
Aug 18 – 23
Top guest favorite
Home in Key West
1880s cottage with a private Jacuzzi
4.92 out of 5 average rating, 326 reviews, 2 bedrooms, 3 beds, 3 baths
Sep 26 – Oct 1
Hotel in Key West
Minutes to Duval + Free Breakfast. Newly Renovated
4.71 out of 5 average rating, 134 reviews, 1 bedroom, 2 beds, 1 bath
Aug 18 – 23
Top guest favorite
Boat in Key West
A 45-ft yacht at a luxury marina
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 30 – Sep 4
Luxe
Home in Key West
Gated luxury with a private marina slip
4.97 out of 5 average rating, 38 reviews, 6 bedrooms, 9 beds, 6.5 baths
Aug 30 – Sep 4
Guest favorite
Condo in Key West
Waterfront penthouse with dock and pool
4.89 out of 5 average rating, 223 reviews, 4 bedrooms, 9 beds, 4 baths
Aug 16 – 21
Top guest favorite
Home in Marathon
Pool, dock, and sailing kayaks on canal
5.0 out of 5 average rating, 87 reviews, 4 bedrooms, 8 beds, 3 baths
Oct 24 – 31
Superhost
Apartment in Key West
Modern 2-story on Duval Street
4.89 out of 5 average rating, 222 reviews, 2 bedrooms, 2 beds, 1.5 baths
Aug 15 – 20
Superhost
Boat in Key West
Luxury houseboat with a rooftop deck
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 16 – 21
Top guest favorite
Apartment in Key West
Beachfront resort with pool and hot tub
4.91 out of 5 average rating, 167 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 26 – 31
Superhost
Home in Key West
Private pool, half a block from Duval
4.92 out of 5 average rating, 88 reviews, 3 bedrooms, 5 beds, 2 baths
Sep 14 – 19