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Search results; Over 1,000 homes in Key West

Top guest favourite
Home in Key West
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
1 bedroom, 1 bed, 1.5 private bathrooms
8–13 Oct
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4.95 out of 5 average rating, 403 reviews
Superhost
Home in Marathon
Waterfront Pool Home w/ Private Dock, Tiki Hut & B
4 bedrooms, 7 beds, 2 bathrooms
28 Nov – 5 Dec
Featured hotel
Room in Key West
High floor island view two queen beds
2 queen beds, 1 bathroom
16–21 Aug
New place to stay
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
16–21 Aug
4.8 out of 5 average rating, 20 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 558 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
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
Top guest favourite
Home in Marathon
Waterfront 6BR Luxury Retreat w/ Pool & Dock
6 bedrooms, 10 beds, 5 bathrooms
3–10 Oct
5.0 out of 5 average rating, 31 reviews
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds, 4.5 bathrooms
22–27 Aug
4.83 out of 5 average rating, 30 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
Guest favourite
Home in Marathon
Lagoona-Matata
3 bedrooms, 4 beds, 2.5 bathrooms
28 Aug – 4 Sept
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Marathon
*NEW* Reel Escape~Dock!~Lift!~Pet Friendly~Grill!
3 bedrooms, 3 beds, 2 bathrooms
22–29 Aug
New place to stay
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
24–31 Oct
5.0 out of 5 average rating, 87 reviews
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
Floralee House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 39 reviews
Guest favourite
Apartment in Key West
Waterfront Condo Dock Pool Downtown Near Duval
2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.91 out of 5 average rating, 276 reviews
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
4.88 out of 5 average rating, 8 reviews
Room in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 king bed, 1 bathroom
16–21 Aug
4.8 out of 5 average rating, 10 reviews
Guest favourite
Home in Marathon
Paradise Villa: a luxury retreat
7 bedrooms, 8 beds, 7.5 bathrooms
8–15 Sept
4.86 out of 5 average rating, 36 reviews