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Search results; Over 1,000 homes in Key West

Top guest favourite
Flat in Key West
Starr's Suite - 2 person K Suite w/Private Spa!
1 bedroom, 1 bed, 1 private bathroom
7–12 Sept
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4.92 out of 5 average rating, 336 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
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
23–28 Aug
4.8 out of 5 average rating, 20 reviews
Featured hotel
Room in Key West
High floor island view two queen beds
2 queen beds, 1 bathroom
17–22 Aug
New place to stay
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
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
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
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
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
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
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
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
25–30 Sept
5.0 out of 5 average rating, 14 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
Top guest favourite
Home in Marathon
Serenity Oasis~Pool!~Putt-Putt!~Kayaks~Bikes~Spa
3 bedrooms, 3 beds, 2 bathrooms
22–29 Aug
5.0 out of 5 average rating, 50 reviews
Luxe
Home in Key West
The Seagate Estate at Lunara Bay
4 bedrooms, 5 beds, 4.5 bathrooms
20–25 Sept
4.81 out of 5 average rating, 63 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
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
Apartment in Key West
Waterfront Condo Dock Pool Near Duval St
2 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
4.89 out of 5 average rating, 150 reviews
Top guest favourite
Flat in Key West
Newly Renovated 2/2 Bath Condo, with shared pool
2 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
4.99 out of 5 average rating, 84 reviews