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Search results; Over 1,000 homes in Key West

Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
1 bedroom, 1 bed
27 Jul – 1 Aug
4.91 out of 5 average rating, 554 reviews
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
2 bedrooms, 4 beds
10–17 Aug
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 38 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Luxe
Home in Key West
Spindrift House at Lunara Bay
4 bedrooms, 7 beds
14–19 Aug
4.85 out of 5 average rating, 95 reviews
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds
27 Aug – 1 Sept
4.83 out of 5 average rating, 111 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds
3–8 Aug
New place to stay
Hotel in Key West
Tropical King
1 bedroom, 1 bed
19–24 Jul
New place to stay
Top guest favourite
Home in Key West
3 Bedroom Home - Perfect Location & Private Pool
3 bedrooms, 4 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 36 reviews
Superhost
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
2 bedrooms, 2 queen beds
20–25 Jul
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds
6–11 Aug
5.0 out of 5 average rating, 4 reviews
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
2 bedrooms, 4 beds
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds
2–7 Aug
4.56 out of 5 average rating, 25 reviews
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds
17–22 Jul
5.0 out of 5 average rating, 22 reviews
Home in Marathon
Updated 4BR view, pet friendly, private pool, dock
4 bedrooms, 7 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Holiday home in Key Colony Beach
Waterfront 4BR | Dual Living | Hot Tub | Dock
4 bedrooms, 4 beds
22–27 Aug
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds
22–27 Aug
4.91 out of 5 average rating, 97 reviews