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Search results; Over 1,000 homes in Key West

Guest favourite
Loft in Key West
Harvey's Haven Studio at the Hollinsed House
Studio, 2 beds, 1 shared bathroom
6–11 Jul
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4.82 out of 5 average rating, 65 reviews
Top guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
4.91 out of 5 average rating, 552 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Top guest favourite
Home in Marathon
Angler’s Terrace Conde Nast Traveler’s Best Airbnb
4.97 out of 5 average rating, 144 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–19 Sept
Luxe
Home in Key West
Spindrift House at Lunara Bay
4.85 out of 5 average rating, 95 reviews, 4 bedrooms, 7 beds, 4 bathrooms
14–19 Aug
Luxe
Home in Marathon
The Pearl at SeaGlass Cove Waterfront Luxury Home!
5 bedrooms, 5 beds, 4.5 bathrooms
9–16 Jul
Luxe
Home in Key West
The Greenmoor House at Lunara Bay
5.0 out of 5 average rating, 10 reviews, 6 bedrooms, 9 beds, 6.5 bathrooms
11–16 Jul
Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
5.0 out of 5 average rating, 76 reviews, 3 bedrooms, 4 beds, 3 bathrooms
11–18 Jul
Top guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
5.0 out of 5 average rating, 20 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
6–11 Jul
Flat in Key West
Beautiful Corner Condo Overlooking Pool
2 bedrooms, 4 beds, 2 bathrooms
8–13 Aug
Top guest favourite
Home in Key West
3 Bedroom Home - Perfect Location & Private Pool
4.97 out of 5 average rating, 36 reviews, 3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
4.83 out of 5 average rating, 110 reviews, 5 bedrooms, 6 beds, 3 bathrooms
27 Aug – 1 Sept
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
New place to stay, 2 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5.0 out of 5 average rating, 37 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
5.0 out of 5 average rating, 26 reviews, 6 bedrooms, 6 beds, 6.5 bathrooms
2–7 Aug
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 97 reviews, 3 bedrooms, 3 beds, 4 bathrooms
22–27 Aug
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 4 beds, 2 bathrooms
25 Aug – 1 Sept
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
New place to stay, 5 bedrooms, 6 beds, 4 bathrooms
11–18 Aug
Luxe
Home in Key West
Catchlight House at Lunara Bay
4.97 out of 5 average rating, 37 reviews, 6 bedrooms, 9 beds, 6.5 bathrooms
27 Jul – 1 Aug
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4.54 out of 5 average rating, 24 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug