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Search results; Over 1,000 homes in Key West

Top guest favourite
Flat in Key West
Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
2 bedrooms, 1 bed, 1 private bathroom
30 Aug – 4 Sept
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4.98 out of 5 average rating, 561 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
6–11 Aug
4.91 out of 5 average rating, 557 reviews
Featured hotel
Room in Key West
Standard queen room
2 queen beds
31 Aug – 5 Sept
New place to stay
Superhost
Home in Key West
Pilar's Secret - walking distance to everything!
3 bedrooms, 5 beds
21–26 Aug
4.92 out of 5 average rating, 88 reviews
Flat in Key West
Apartment in Key west
1 bedroom, 1 queen bed
8–13 Aug
New place to stay
Superhost
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
2 bedrooms, 2 queen beds
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Luxe
Home in Key West
Catchlight House at Lunara Bay
6 bedrooms, 9 beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 38 reviews
Guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 8 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
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
Guest favourite
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, 6 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds
22–29 Aug
5.0 out of 5 average rating, 86 reviews
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds
30 Aug – 4 Sept
4.86 out of 5 average rating, 42 reviews
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds
18–23 Aug
New place to stay
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds
6–11 Aug
4.56 out of 5 average rating, 25 reviews
Luxe
Home in Key West
The Seagate Estate at Lunara Bay
4 bedrooms, 5 beds
16–21 Aug
4.81 out of 5 average rating, 62 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, 101 reviews
Featured hotel
Room in Key West
Ocean view one king bed
7–12 Aug
New place to stay
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 4 reviews