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Search results; Over 1,000 homes in Key West

Guest favourite
Holiday home in Key West
Historic Cigar House. 3rd floor Suite W/Kitchen
1 bedroom, 2 beds, 1 private bathroom
6–11 Jul
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4.85 out of 5 average rating, 387 reviews
Top guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
4.91 out of 5 average rating, 551 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Jul
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
New place to stay, 2 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
New place to stay, 2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Luxe
Home in Key West
Catchlight House at Lunara Bay
4.97 out of 5 average rating, 37 reviews, 6 bedrooms, 9 beds, 6.5 bathrooms
14–19 Jul
Top guest favourite
Home in Key West
3 Bedroom Home - Perfect Location & Private Pool
4.97 out of 5 average rating, 36 reviews, 3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
Luxe
Home in Key West
Evershore Estate at Lunara Bay | Wellness Home
4.93 out of 5 average rating, 111 reviews, 4 bedrooms, 7 beds, 4 bathrooms
5–10 Jul
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
2 bedrooms, 2 beds, 2 bathrooms
1–6 Jul
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
4.97 out of 5 average rating, 199 reviews, 2 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
Guest favourite
Houseboat in Key West
Tiki Suites~The Grand Tiki~Private Water Stay
4.92 out of 5 average rating, 354 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Jul
Top guest favourite
Home in Marathon
Angler’s Terrace Conde Nast Traveler’s Best Airbnb
4.97 out of 5 average rating, 144 reviews, 4 bedrooms, 6 beds, 3 bathrooms
12–19 Sept
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
New place to stay, 5 bedrooms, 6 beds, 4 bathrooms
11–18 Aug
Flat in Key West
Beautiful Corner Condo Overlooking Pool
2 bedrooms, 4 beds, 2 bathrooms
8–13 Aug
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
4.83 out of 5 average rating, 110 reviews, 5 bedrooms, 6 beds, 3 bathrooms
27 Aug – 1 Sept
Top guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
5.0 out of 5 average rating, 19 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
5–10 Jul
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
5.0 out of 5 average rating, 26 reviews, 6 bedrooms, 6 beds, 6.5 bathrooms
2–7 Aug
Guest favourite
Boat in Key West
43' Classic Yacht Views, Pools, Duval Shuttle
4.83 out of 5 average rating, 24 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
17–22 Jul
Superhost
Houseboat in Key West
Amazing houseboat with 2nd floor observation deck
4.92 out of 5 average rating, 177 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Jul
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
5.0 out of 5 average rating, 8 reviews, 6 bedrooms, 10 beds, 6 bathrooms
16–21 Aug