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Search results; Over 1,000 homes in Key West

Top guest favourite
Home in Key West
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
1 bedroom, 2 beds, 1 private bathroom
10–15 Aug
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4.97 out of 5 average rating, 316 reviews
Superhost
Home in Marathon
*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!
4 bedrooms, 5 beds
2–9 Aug
New place to stay
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
27 Jul – 1 Aug
4.91 out of 5 average rating, 554 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds
5–10 Oct
4.91 out of 5 average rating, 97 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 38 reviews
Home in Marathon
4BR Gulffront Dog Friendly | Pool | Dock | Deck
4 bedrooms, 4 beds
16–23 Aug
4.71 out of 5 average rating, 7 reviews
Luxe
Home in Key West
Spindrift House at Lunara Bay
4 bedrooms, 7 beds
13–18 Sept
4.85 out of 5 average rating, 96 reviews
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds
27 Aug – 1 Sept
4.83 out of 5 average rating, 111 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Superhost
Villa in Key West
Coral Villa by AvantStay| Close 2 DT Key West!
3 bedrooms, 5 beds
8–13 Aug
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
2 bedrooms, 4 beds
9–16 Aug
5.0 out of 5 average rating, 9 reviews
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 4 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds
23–28 Aug
New place to stay
Featured hotel
Room in Key West
Adults-Only Pension – Standard King
1 king bed
2–7 Aug
4.83 out of 5 average rating, 23 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds
2–7 Aug
4.56 out of 5 average rating, 25 reviews
Luxe
Home in Key West
Catchlight House at Lunara Bay
6 bedrooms, 9 beds
27 Jul – 1 Aug
4.97 out of 5 average rating, 37 reviews
Room in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 king bed
13–18 Sept
New place to stay
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
6 bedrooms, 6 beds
2–7 Aug
5.0 out of 5 average rating, 27 reviews
Luxe
Home in Key West
The Greenmoor House at Lunara Bay
6 bedrooms, 9 beds
1–6 Aug
5.0 out of 5 average rating, 11 reviews