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Search results; Over 1,000 homes in Key West

Guest favourite
Apartment in Key West
Fully renovated 2/2 bath condo w/ shared pool!
2 bedrooms, 3 beds, 2 private bathrooms
12–17 Sept
,
4.95 out of 5 average rating, 208 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
6–11 Aug
4.91 out of 5 average rating, 557 reviews
Home in Marathon
Casa Entera Frente al Mar + Muelle 50'
3 bedrooms, 4 beds, 2 bathrooms
8–15 Aug
New place to stay
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
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, 86 reviews
Top guest favourite
Apartment in Key West
Free Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 5 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
Flat in Key West
Apartment in Key west
1 bedroom, 1 queen bed, 1 bathroom
8–13 Aug
New place to stay
Superhost
Apartment in Key West
The Tahiti Suite | Updated Key West Condo w/ Pool!
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Home in Marathon
Waterfront 6BR Luxury Retreat w/ Pool & Dock
6 bedrooms, 10 beds, 5 bathrooms
3–10 Oct
5.0 out of 5 average rating, 31 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
Luxe
Home in Key West
The Seagate Estate at Lunara Bay
4 bedrooms, 5 beds, 4.5 bathrooms
20–25 Sept
4.81 out of 5 average rating, 62 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
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
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 Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
7–12 Aug
4.56 out of 5 average rating, 25 reviews
Home in Marathon
Marlin House | Waterfront Pool Home Near Marina
2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 3 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
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, 7 reviews