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Search results; Over 1,000 homes in Key West

Guest favourite
Houseboat in Key West
Key West Outpost: eco-vacation
2 bedrooms, 2 beds, 1 shared bathroom
15–20 Aug
,
4.95 out of 5 average rating, 83 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
18–23 Aug
4.91 out of 5 average rating, 557 reviews
Superhost
Home in Marathon
*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!
4 bedrooms, 5 beds, 3 bathrooms
11–18 Sept
New place to stay
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
16–21 Aug
4.79 out of 5 average rating, 19 reviews
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
26 Sept – 1 Oct
4.83 out of 5 average rating, 111 reviews
Guest favourite
Apartment in Key West
Waterfront Dock Pool Near Duval St Penthouse
4 bedrooms, 9 beds, 4 bathrooms
16–21 Aug
4.91 out of 5 average rating, 211 reviews
Home in Cudjoe Key
NEW Listing•Solace by the Sea•Ocean Views
2 bedrooms, 3 beds, 2 bathrooms
20–25 Aug
New place to stay
Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
30 Aug – 4 Sept
4.86 out of 5 average rating, 43 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
20–25 Aug
4.56 out of 5 average rating, 25 reviews
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Away Awai Floating Vill
2 bedrooms, 2 queen beds, 2 bathrooms
21–26 Aug
4.93 out of 5 average rating, 85 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
4.91 out of 5 average rating, 102 reviews
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
6 bedrooms, 6 beds, 6.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 28 reviews
Luxe
Home in Key West
Floralee House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 38 reviews
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds, 3.5 bathrooms
12–19 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Key West
Waterfront Home in Key Cove Landings
4 bedrooms, 6 beds, 3 bathrooms
16–21 Aug
5.0 out of 5 average rating, 24 reviews
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds, 3 bathrooms
18–23 Aug
New place to stay
Top guest favourite
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
2 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 7 reviews
Apartment in Key West
2BR 4th-Floor | Balcony | Pool
2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
New place to stay