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Search results; Over 1,000 homes in Key West

Guest favourite
Cottage in Key West
The Dancing Rooster - 1 Block to Duval!
3 bedrooms, 3 beds, 2 private bathrooms
28 Nov – 3 Dec
,
4.91 out of 5 average rating, 170 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
6–11 Aug
4.91 out of 5 average rating, 557 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds
22–29 Aug
5.0 out of 5 average rating, 86 reviews
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds
5–10 Oct
4.91 out of 5 average rating, 101 reviews
Luxe
Home in Key West
Catchlight House at Lunara Bay
6 bedrooms, 9 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 38 reviews
Superhost
Home in Key West
Pilar's Secret - walking distance to everything!
3 bedrooms, 5 beds
21–26 Aug
4.92 out of 5 average rating, 88 reviews
Superhost
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
2 bedrooms, 2 queen beds
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Key West
Fleming Street 2/1 private home Key West getaway
2 bedrooms, 4 beds
17–22 Aug
4.91 out of 5 average rating, 135 reviews
Superhost
Hotel in Key West
Boardwalk Studio off Mallory Sq in Old Town Steps
1 king bed
18–24 Apr
New place to stay
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds
30 Aug – 4 Sept
4.86 out of 5 average rating, 42 reviews
Featured hotel
Room in Key West
Standard queen room
2 queen beds
26–31 Aug
New place to stay
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, 14 reviews
Superhost
Apartment in Key West
Glimmer Glass oceanfront condo by Rent Key West
2 bedrooms, 3 beds
20–26 Aug
4.95 out of 5 average rating, 20 reviews
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds
18–23 Aug
New place to stay
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
Flat in Key West
Apartment in Key west
1 bedroom, 1 queen bed
8–13 Aug
New place to stay
Luxe
Home in Key West
The Seagate Estate at Lunara Bay
4 bedrooms, 5 beds
16–21 Aug
4.81 out of 5 average rating, 62 reviews
Superhost
Home in Key West
Mango Cottage, a charming Key West home ready for
3 bedrooms, 4 beds
27 Aug – 1 Sept
4.91 out of 5 average rating, 130 reviews