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Search results; Over 1,000 homes in Key West

Guest favourite
Holiday home in Key West
Historic Cigar House. 3rd floor Suite W/Kitchen
1 bedroom, 2 beds, 1 private bathroom
10–15 Jul
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4.85 out of 5 average rating, 388 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
1 bedroom, 1 bed, 1 bathroom
3–8 Aug
4.91 out of 5 average rating, 553 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
12–17 Jul
New place to stay
Top guest favourite
Home in Key West
3 Bedroom Home - Perfect Location & Private Pool
3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 36 reviews
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
9–14 Jul
4.86 out of 5 average rating, 42 reviews
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
27 Aug – 1 Sept
4.83 out of 5 average rating, 111 reviews
Flat in Key West
Beautiful Corner Condo Overlooking Pool
2 bedrooms, 4 beds, 2 bathrooms
8–13 Aug
Luxe
Home in Key West
The Seagate Estate at Lunara Bay
4 bedrooms, 5 beds, 4.5 bathrooms
16–21 Aug
4.8 out of 5 average rating, 59 reviews
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds, 4.5 bathrooms
17–22 Jul
5.0 out of 5 average rating, 21 reviews
Luxe
Home in Marathon
The Pearl at SeaGlass Cove Waterfront Luxury Home!
5 bedrooms, 5 beds, 4.5 bathrooms
9–16 Jul
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
4.56 out of 5 average rating, 25 reviews
Featured hotel
Hotel in Key West
Classic King City/Balcony
1 bedroom, 1 king bed, 1 bathroom
12–17 Jul
4.91 out of 5 average rating, 22 reviews
Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
3 bedrooms, 4 beds, 3 bathrooms
11–18 Jul
5.0 out of 5 average rating, 76 reviews
Guest favourite
Houseboat in Key West
Tiki Suites~The Grand Tiki~Private Water Stay
1 bedroom, 1 bed, 1 bathroom
25–30 Jul
4.92 out of 5 average rating, 356 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Luxe
Home in Key West
Catchlight House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
27 Jul – 1 Aug
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 38 reviews
Home in Marathon
Special-New Oceanfront Home-5Ksf under $1K a nite!
5 bedrooms, 5 beds, 4.5 bathrooms
14–21 Jul
New place to stay