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Search results; Over 1,000 homes in Key West

Guest favourite
Home in Key West
Stunning Townhouse * Full kitchen! * Sleeps 6
2 bedrooms, 3 beds, 2.5 private bathrooms
17–22 Oct
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4.94 out of 5 average rating, 319 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
22–29 Aug
5.0 out of 5 average rating, 85 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
18–23 Aug
4.91 out of 5 average rating, 556 reviews
Home in Marathon
Keys Coastal Getaway | King + 2Q | 10 Min Sombrero
2 bedrooms, 3 beds, 2 bathrooms
1–8 Aug
New place to stay
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 4 reviews
Home in Marathon
4BR Gulffront Dog Friendly | Pool | Dock | Deck
4 bedrooms, 4 beds, 2.5 bathrooms
16–23 Aug
4.71 out of 5 average rating, 7 reviews
Luxe
Home in Key West
The Seagate Estate at Lunara Bay
4 bedrooms, 5 beds, 4.5 bathrooms
16–21 Aug
4.81 out of 5 average rating, 62 reviews
Luxe
Home in Key West
The Greenmoor House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
4.91 out of 5 average rating, 101 reviews
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
26 Sept – 1 Oct
4.83 out of 5 average rating, 111 reviews
Guest favourite
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
2 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 38 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
4.56 out of 5 average rating, 25 reviews
Top guest favourite
Apartment in Key West
Coastline Comfort
2 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 7 reviews
Superhost
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
2 bedrooms, 2 queen beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds, 4.5 bathrooms
2–7 Aug
4.82 out of 5 average rating, 28 reviews
Superhost
Home in Key West
Mango Cottage, a charming Key West home ready for
3 bedrooms, 4 beds, 2 bathrooms
27 Aug – 1 Sept
4.91 out of 5 average rating, 130 reviews