filters

Search results; Over 1,000 homes in Key West

Featured hotel
Room in Key West
Classic Double Queen City/Balcony
1 bedroom, 1 private bath
Aug 26 – 31
,
4.8 out of 5 average rating, 59 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
Superhost
Villa in Marathon
On the water in a private marina
4.86 out of 5 average rating, 602 reviews, 1 bedroom, 2 beds, 1 bath
Aug 17 – 22
Featured hotel
Room in Key West
Superior King Pool/Balcony
4.73 out of 5 average rating, 15 reviews, 1 king bed, 1 bath
Aug 16 – 21
Guest favorite
Houseboat in Marathon
Houseboat anchored in the mangroves
4.92 out of 5 average rating, 90 reviews, 1 bedroom, 1 bed, 1 bath
Sep 27 – Oct 2
Top guest favorite
Condo in Key West
Top-floor wrap-around balcony with water views
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 4 beds, 2 baths
Sep 22 – 27
Top guest favorite
Boat in Key West
Private catamaran with captain and snorkeling
4.88 out of 5 average rating, 176 reviews, 3 bedrooms, 3 beds, 2.5 baths
Aug 17 – 22
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
One king bed
New place to stay, 1 bath
Aug 12 – 17
Guest favorite
Houseboat in Key West
Private floating bungalow, boat-access only
4.92 out of 5 average rating, 358 reviews, 1 bedroom, 1 bed, 1 bath
Aug 25 – 30
Top guest favorite
Apartment in Key West
Renovated with sunset views and a pool
4.99 out of 5 average rating, 84 reviews, 2 bedrooms, 3 beds, 2 baths
Aug 30 – Sep 4
Guest favorite
Boat in Key West
Luxury houseboat with 3 decks and rooftop
4.93 out of 5 average rating, 85 reviews, 2 bedrooms, 2 beds, 2 baths
Aug 21 – 26
Guest favorite
Vacation home in Key West
Historic Cigar House, 3 blocks from Duval
4.85 out of 5 average rating, 392 reviews, 1 bedroom, 2 beds, 1 bath
Sep 14 – 19
Guest favorite
Boat in Key West
Sleep on deck under the stars
4.9 out of 5 average rating, 244 reviews, 1 bedroom, 2 beds, 1 bath
Sep 1 – 6
Guest favorite
Condo in Summerland Key
New resort suite with pool and marina
4.97 out of 5 average rating, 36 reviews, 1 bedroom, 4 beds, 1 bath
Aug 16 – 21
Top guest favorite
Apartment in Key West
Renovated 1880s cigar maker’s cottage with spa
4.92 out of 5 average rating, 277 reviews, 2 bedrooms, 2 beds, 3 baths
Aug 23 – 28
Top guest favorite
Home in Summerland Key
Wrap-around balcony with waterfront views
4.97 out of 5 average rating, 33 reviews, 1 bedroom, 3 beds, 1 bath
Aug 23 – 28
Guest favorite
Apartment in Key West
Loft suite with a Duval Street balcony
5.0 out of 5 average rating, 7 reviews, 1 bedroom, 2 beds, 1.5 baths
Aug 16 – 21
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