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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, 207 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
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
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
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
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
Superhost
Home in Key West
Mango Cottage, a charming Key West home ready for
3 bedrooms, 4 beds
27 Aug – 1 Sept
4.91 out of 5 average rating, 130 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 14 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
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds
3–8 Aug
4.97 out of 5 average rating, 32 reviews
Superhost
Home in Key West
Fleming Street 2/1 private home Key West getaway
2 bedrooms, 4 beds
14–19 Aug
4.91 out of 5 average rating, 135 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds
24–29 Sept
4.97 out of 5 average rating, 205 reviews
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds
18–23 Aug
New place to stay
Home in Marathon
Private Island Beach House on Tingler Island
4 bedrooms, 5 beds
8–15 Aug
Guest favourite
Home in Key West
Paradise found
3 bedrooms, 4 beds
26–31 Aug
4.93 out of 5 average rating, 153 reviews
Top guest favourite
Flat in Key West
Newly Renovated 2/2 Bath Condo, with shared pool
2 bedrooms, 3 beds
10–15 Aug
4.99 out of 5 average rating, 84 reviews
Top guest favourite
Home in Key Colony Beach
Captain’s Quarters Ahoy Mateys! Florida, Keys
2 bedrooms, 2 beds
19–25 Aug
4.93 out of 5 average rating, 147 reviews
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds
3–8 Aug
4.86 out of 5 average rating, 42 reviews
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Away Awai Floating Vill
2 bedrooms, 2 queen beds
4–9 Aug
4.93 out of 5 average rating, 84 reviews