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Search results; Over 1,000 homes in Key West

Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds
23–28 Aug
4.82 out of 5 average rating, 22 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
23–28 Aug
4.91 out of 5 average rating, 558 reviews
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds
26 Sept – 1 Oct
4.83 out of 5 average rating, 111 reviews
Superhost
Home in Marathon
*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!
4 bedrooms, 5 beds
11–18 Sept
New place to stay
Guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds
12–17 Sept
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Key West
Casa Loca! By Rent Key West Vacations 1/2 block
3 bedrooms, 4 beds
20–25 Aug
4.9 out of 5 average rating, 91 reviews
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
6 bedrooms, 6 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 28 reviews
Featured hotel
Room in Key West
High floor island view two queen beds
2 queen beds
19–24 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, 102 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds
20–25 Aug
4.56 out of 5 average rating, 25 reviews
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds
24–29 Aug
4.88 out of 5 average rating, 8 reviews
Hotel in Key West
Minutes to Duval + Free Breakfast. Newly Renovated
1 bedroom, 2 queen beds
25–30 Aug
4.71 out of 5 average rating, 136 reviews
Luxe
Home in Key West
The Seagate Estate at Lunara Bay
4 bedrooms, 5 beds
20–25 Sept
4.81 out of 5 average rating, 63 reviews
Superhost
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
2 bedrooms, 2 queen beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 4 reviews
Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds
28 Aug – 2 Sept
New place to stay
Top guest favourite
Home in Marathon
Waterfront 6BR Luxury Retreat w/ Pool & Dock
6 bedrooms, 10 beds
3–10 Oct
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds
3–8 Sept
4.96 out of 5 average rating, 207 reviews
Guest favourite
Home in Key West
Waterfront Home in Key Cove Landings
4 bedrooms, 6 beds
21–26 Aug
5.0 out of 5 average rating, 24 reviews