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Search results; Over 1,000 homes in Key West

Guest favourite
Flat in Key West
KW Luxury 2/2 Beachfront resort Tropical Oasis
2 bedrooms, 3 beds, 2 private bathrooms
3–8 Jul
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4.92 out of 5 average rating, 200 reviews
Top 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, 551 reviews
Luxe
Home in Key West
Spindrift House at Lunara Bay
4 bedrooms, 7 beds, 4 bathrooms
14–19 Aug
4.85 out of 5 average rating, 95 reviews
Top guest favourite
Home in Marathon
Angler’s Terrace Conde Nast Traveler’s Best Airbnb
4 bedrooms, 6 beds, 3 bathrooms
12–19 Sept
4.97 out of 5 average rating, 144 reviews
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
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 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
4 bedrooms, 7 beds, 4.5 bathrooms
26 Sept – 3 Oct
5.0 out of 5 average rating, 13 reviews
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
2 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
New place to stay
Top guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds, 4.5 bathrooms
4–9 Jul
5.0 out of 5 average rating, 19 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
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
4.54 out of 5 average rating, 24 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds, 3.5 bathrooms
12–19 Sept
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, 4 bathrooms
22–27 Aug
4.91 out of 5 average rating, 97 reviews
Flat in Key West
Beautiful Corner Condo Overlooking Pool
2 bedrooms, 4 beds, 2 bathrooms
8–13 Aug
Luxe
Home in Key West
Floralee House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
2–7 Jul
4.97 out of 5 average rating, 35 reviews
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
5 bedrooms, 6 beds, 4 bathrooms
11–18 Aug
New place to stay
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Awai's Floating Villa
2 bedrooms, 2 queen beds, 2 bathrooms
6–11 Jul
4.93 out of 5 average rating, 82 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, 110 reviews