filters

Search results; Over 1,000 homes in Key West

Superhost
Cottage in Key West
Ann Street Tranquility
1 bedroom, 1 bed, 1 shared bath
Aug 16 – 21
,
4.77 out of 5 average rating, 22 reviews
Guest favorite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bath
Aug 18 – 23
4.91 out of 5 average rating, 557 reviews
Top guest favorite
Condo in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds, 2 baths
Aug 23 – 28
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds, 3.5 baths
Aug 29 – Sep 5
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Key West
Mango Cottage, a charming Key West home ready for
3 bedrooms, 4 beds, 2 baths
Aug 27 – Sep 1
4.91 out of 5 average rating, 130 reviews
Hotel in Key West
Minutes to Duval + Free Breakfast. Newly Renovated
1 bedroom, 2 queen beds, 1 bath
Aug 18 – 23
4.71 out of 5 average rating, 134 reviews
Featured hotel
Room in Key West
Pool view one king bed accessible
1 bath
Aug 19 – 24
New place to stay
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds, 3 baths
Aug 18 – 23
New place to stay
Top guest favorite
Home in Marathon
Waterfront 6BR Luxury Retreat w/ Pool & Dock
6 bedrooms, 10 beds, 5 baths
Oct 3 – 10
5.0 out of 5 average rating, 31 reviews
Guest favorite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds, 2 baths
Aug 24 – 29
4.86 out of 5 average rating, 7 reviews
Top guest favorite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 10 reviews
Top guest favorite
Home in Key West
Family House, 2 K BR's, Private Spa/Deck, 2 pools.
2 bedrooms, 3 beds, 3 baths
Sep 26 – Oct 1
4.92 out of 5 average rating, 326 reviews
Luxe
Home in Key West
Catchlight House at Lunara Bay
6 bedrooms, 9 beds, 6.5 baths
Aug 30 – Sep 4
4.97 out of 5 average rating, 39 reviews
Top guest favorite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 baths
Oct 24 – 31
5.0 out of 5 average rating, 87 reviews
Guest favorite
Condo in Key West
Waterfront Dock Pool Pet Friendly Near Duval St
4 bedrooms, 9 beds, 4 baths
Aug 16 – 21
4.89 out of 5 average rating, 223 reviews
Superhost
Apartment in Key West
Island Color Suite
2 bedrooms, 2 beds, 1.5 baths
Aug 15 – 20
4.89 out of 5 average rating, 222 reviews
Superhost
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
2 bedrooms, 2 queen beds, 2 baths
Aug 16 – 21
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Apartment in Key West
Key West Beachside 1400sf, 2 Bedroom Condo
2 bedrooms, 2 king beds, 2 baths
Aug 26 – 31
4.91 out of 5 average rating, 167 reviews
Top guest favorite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bath
Aug 23 – 28
4.97 out of 5 average rating, 33 reviews