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Search results; Over 1,000 homes in Key West

Guest favorite
Soak in Atlantic views from your expansive balcony at this Key West condo
2 bedrooms, 3 beds, 2 private baths
Aug 12 – 17
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4.89 out of 5 average rating, 107 reviews
Guest favorite
This off-grid floating bungalow in Key West puts you among dolphins and open water
4.91 out of 5 average rating, 557 reviews, 1 bedroom, 1 bed, 1 bath
Aug 18 – 23
Top guest favorite
This waterfront Key West condo gives you a private boat slip and heated pool
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 2 baths
Aug 23 – 28
Superhost
Look out over open water from this Key Colony Beach house with a pool and dock
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 4 beds, 3.5 baths
Aug 29 – Sep 5
Superhost
This historic conch house gives you a heated saltwater pool in Key West
4.91 out of 5 average rating, 130 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 27 – Sep 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
Featured hotel
Room in Key West
Pool view one king bed accessible
New place to stay, 1 bath
Aug 19 – 24
Superhost
This Coral Hammock townhome puts you poolside with alfresco dining and a patio
New place to stay, 3 bedrooms, 6 beds, 3 baths
Aug 18 – 23
Top guest favorite
This waterfront Marathon house gives you a heated pool, spa, and 100-foot dock
5.0 out of 5 average rating, 31 reviews, 6 bedrooms, 10 beds, 5 baths
Oct 3 – 10
Guest favorite
This waterfront Cudjoe Key house gives you a private dock and saltwater pool
4.86 out of 5 average rating, 7 reviews, 2 bedrooms, 4 beds, 2 baths
Aug 24 – 29
Top guest favorite
Wake to the water aboard a 45-ft yacht at this Key West marina
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 30 – Sep 4
Top guest favorite
This 1880s Key West cottage puts you half a block from Duval with a private jacuzzi
4.92 out of 5 average rating, 326 reviews, 2 bedrooms, 3 beds, 3 baths
Sep 26 – Oct 1
Luxe
This gated Key West house gives you a private pool, marina slip, and fire pit
4.97 out of 5 average rating, 39 reviews, 6 bedrooms, 9 beds, 6.5 baths
Aug 30 – Sep 4
Top guest favorite
This Marathon waterfront house gives you a heated pool, dock, and sailing kayaks
5.0 out of 5 average rating, 87 reviews, 4 bedrooms, 8 beds, 3 baths
Oct 24 – 31
Guest favorite
This two-story Key West penthouse gives you marina views from dual balconies
4.89 out of 5 average rating, 223 reviews, 4 bedrooms, 9 beds, 4 baths
Aug 16 – 21
Superhost
Sip cocktails on your balcony at this 2-story Duval Street apartment
4.89 out of 5 average rating, 222 reviews, 2 bedrooms, 2 beds, 1.5 baths
Aug 15 – 20
Superhost
Watch the sunrise from your rooftop on this Key West houseboat with a heated pool
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 16 – 21
Top guest favorite
This beachfront Key West condo gives you a heated pool, jacuzzi, and private veranda
4.91 out of 5 average rating, 167 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 26 – 31
Top guest favorite
Soak in waterfront views from the wrap-around balcony at this Sugarloaf Key home
4.97 out of 5 average rating, 33 reviews, 1 bedroom, 3 beds, 1 bath
Aug 23 – 28