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Search results; Over 1,000 homes in Key West

Guest favourite
Apartment in Key West
Condo de Paradise/Salt Water Pool/Boat Dock
2 bedrooms, 3 beds, 2 private bathrooms
5–12 Aug
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4.96 out of 5 average rating, 45 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 ~ Floating Bungalows
4.91 out of 5 average rating, 554 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
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
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
New place to stay, 2 queen beds, 1 bathroom
16–21 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 Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 98 reviews, 3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
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
Luxe
Home in Key West
Spindrift House at Lunara Bay
4.85 out of 5 average rating, 96 reviews, 4 bedrooms, 7 beds, 4 bathrooms
13–18 Sept
Home in Marathon
4BR Gulffront Dog Friendly | Pool | Dock | Deck
4.71 out of 5 average rating, 7 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
16–23 Aug
Luxe
Home in Key West
The Greenmoor House at Lunara Bay
5.0 out of 5 average rating, 11 reviews, 6 bedrooms, 9 beds, 6.5 bathrooms
1–6 Aug
Superhost
Villa in Key West
Coral Villa by AvantStay| Close 2 DT Key West!
3 bedrooms, 5 beds, 3 bathrooms
8–13 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
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
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms, 5 bathrooms
25 Jul – 1 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
3–8 Aug
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Superhost
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
2 bedrooms, 2 beds, 2 bathrooms
21–26 Jul