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Search results; Over 1,000 homes in Key West

Superhost
Cottage in Key West
Ann Street Cottage
1 bedroom, 1 bed, 1.5 shared bathrooms
27 Jul – 1 Aug
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4.83 out of 5 average rating, 12 reviews
Superhost
Home in Marathon
*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
2–9 Aug
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
4.91 out of 5 average rating, 554 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
New place to stay, 1 bedroom, 2 beds, 1 bathroom
28 Sept – 3 Oct
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 2 bathrooms
6–11 Aug
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
4.83 out of 5 average rating, 111 reviews, 5 bedrooms, 6 beds, 3 bathrooms
27 Aug – 1 Sept
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5.0 out of 5 average rating, 38 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
Featured hotel
Hotel in Key West
Ocean view one king bed
New place to stay, 1 bedroom, 1 bathroom
7–12 Aug
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Awai's Floating Villa
4.93 out of 5 average rating, 84 reviews, 2 bedrooms, 2 beds, 2 bathrooms
4–9 Aug
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
4.97 out of 5 average rating, 30 reviews, 1 bedroom, 3 beds, 1 bathroom
24–29 Jul
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
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
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4.56 out of 5 average rating, 25 reviews, 4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 4 beds, 2 bathrooms
9–16 Aug
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
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Guest favourite
Houseboat in Key West
Tiki Suites~The Grand Tiki~Private Water Stay
4.92 out of 5 average rating, 356 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 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
1–6 Aug
Featured hotel
Hotel in Key West
Adults-Only Pension – Standard King
4.81 out of 5 average rating, 21 reviews, 1 bedroom, 1 bathroom
18–23 Jul