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Search results; Over 1,000 homes in Key West

Guest favourite
Townhouse in Key West
Exceptional Water View With Boat Dock!
1 bedroom, 1 bed, 2 private bathrooms
9–16 Aug
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5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
5.0 out of 5 average rating, 85 reviews, 4 bedrooms, 8 beds, 3 bathrooms
15–22 Aug
Superhost
Home in Key West
Pilar's Secret - walking distance to everything!
4.92 out of 5 average rating, 88 reviews, 3 bedrooms, 5 beds, 2 bathrooms
21–26 Aug
Guest favourite
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
5.0 out of 5 average rating, 9 reviews, 2 queen beds, 1 bathroom
3–8 Sept
Superhost
Home in Key West
Fleming Street 2/1 private home Key West getaway
4.91 out of 5 average rating, 135 reviews, 2 bedrooms, 4 beds, 1 bathroom
4–9 Aug
Superhost
Apartment in Key West
The Cuban House @ Cuban Club Suites
4.76 out of 5 average rating, 178 reviews, 1 bedroom, 3 beds, 1.5 bathrooms
2–7 Aug
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
4.91 out of 5 average rating, 555 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 Aug
Luxe
Home in Key West
The Seagate Estate at Lunara Bay
4.81 out of 5 average rating, 62 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
16–21 Aug
Superhost
Apartment in Key West
Glimmer Glass oceanfront condo by Rent Key West
4.95 out of 5 average rating, 20 reviews, 2 bedrooms, 3 beds, 2 bathrooms
7–13 Aug
Guest favourite
Home in Key Colony Beach
4/2.5 Waterfront home on Key Colony, Pool, Dockage
4.85 out of 5 average rating, 39 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
14–21 Aug
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 101 reviews, 3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
Top guest favourite
Flat in Key West
Newly Renovated 2/2 Bath Condo, with shared pool
4.99 out of 5 average rating, 83 reviews, 2 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
Guest favourite
Home in Key West
Paradise found
4.94 out of 5 average rating, 151 reviews, 3 bedrooms, 4 beds, 3 bathrooms
26–31 Aug
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4.82 out of 5 average rating, 28 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
1–6 Aug
Guest favourite
Flat in Key West
Key West Beach House
5.0 out of 5 average rating, 16 reviews, 2 bedrooms, 2 beds, 2 bathrooms
1–8 Aug
Guest favourite
Flat in Key West
Cayo-Hueso Suite | Chic 1BR + Balcony in
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
1–6 Aug
Guest favourite
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
4.83 out of 5 average rating, 111 reviews, 5 bedrooms, 6 beds, 3 bathrooms
26 Sept – 1 Oct