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Search results; Over 1,000 homes in Key West

Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 private bathroom
27 Jul – 1 Aug
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4.91 out of 5 average rating, 554 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
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
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 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
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
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
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds
23–28 Aug
New place to stay
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
Featured hotel
Room in Key West
Pool view one bedroom suite
7–12 Aug
New place to stay
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
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
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Room in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 king bed
13–18 Sept
New place to stay
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 5 reviews
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
2 bedrooms, 4 beds
7–12 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Key West
Family House, 2 K BR's, Private Spa/Deck, 2 pools.
2 bedrooms, 3 beds
7–12 Aug
4.92 out of 5 average rating, 324 reviews