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Search results; Over 1,000 homes in Key West

Guest favourite
Flat in Key West
The Bartlum - Steps to Duval Street
1 bedroom, 2 beds, 1 private bathroom
10–15 Jul
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4.86 out of 5 average rating, 264 reviews
Top guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
4.91 out of 5 average rating, 551 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
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
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
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 Summerland Key
Waterfront Beach House with Dock & Heated Pool!
5.0 out of 5 average rating, 12 reviews, 4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
Luxe
Home in Marathon
The Pearl at SeaGlass Cove Waterfront Luxury Home!
5 bedrooms, 5 beds, 4.5 bathrooms
9–16 Jul
Top guest favourite
Home in Marathon
Water Views | Private Pool Oasis + Gazebo + Kayaks
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 7 beds, 4.5 bathrooms
26 Sept – 3 Oct
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
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
5.0 out of 5 average rating, 19 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
4–9 Jul
Luxe
Home in Key West
Altair House at Lunara Bay
4.86 out of 5 average rating, 42 reviews, 6 bedrooms, 9 beds, 6.5 bathrooms
9–14 Jul
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
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5.0 out of 5 average rating, 27 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
12–19 Sept
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
Flat in Key West
Beautiful Corner Condo Overlooking Pool
2 bedrooms, 4 beds, 2 bathrooms
8–13 Aug
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
Floralee House at Lunara Bay
4.97 out of 5 average rating, 35 reviews, 6 bedrooms, 9 beds, 6.5 bathrooms
2–7 Jul
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
Guest favourite
Houseboat in Key West
Tiki Suites~The Grand Tiki~Private Water Stay
4.92 out of 5 average rating, 354 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Jul