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Search results; Over 1,000 homes in Key West

Guest favourite
Cottage in Key West
Colony Poolside: A charming bungalow near Duval
1 bedroom, 2 beds, 1 shared bathroom
1–6 Jul
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4.82 out of 5 average rating, 22 reviews
Top guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
1 bedroom, 1 bed, 1 bathroom
3–8 Jul
4.91 out of 5 average rating, 551 reviews
Top guest favourite
Home in Key West
3 Bedroom Home - Perfect Location & Private Pool
3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 36 reviews
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
5 bedrooms, 6 beds, 4 bathrooms
11–18 Aug
New place to stay
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bathroom
12–17 Jul
4.96 out of 5 average rating, 28 reviews
Guest favourite
Boat in Key West
43' Classic Yacht Views, Pools, Duval Shuttle
2 bedrooms, 2 queen beds, 1.5 bathrooms
12–17 Jul
4.83 out of 5 average rating, 24 reviews
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Jul
Flat in Key West
Beautiful Corner Condo Overlooking Pool
2 bedrooms, 4 beds, 2 bathrooms
8–13 Aug
Luxe
Home in Key West
The Seagate Estate at Lunara Bay
4 bedrooms, 5 beds, 4.5 bathrooms
6–11 Jul
4.79 out of 5 average rating, 58 reviews
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
2 bedrooms, 4 beds, 2.5 bathrooms
12–17 Jul
New place to stay
Top guest favourite
Home in Marathon
Angler’s Terrace Conde Nast Traveler’s Best Airbnb
4 bedrooms, 6 beds, 3 bathrooms
12–19 Sept
4.97 out of 5 average rating, 143 reviews
Superhost
Villa in Key West
Coral Villa by AvantStay| Close 2 DT Key West!
3 bedrooms, 5 beds, 3 bathrooms
4–9 Jul
New place to stay
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds, 4.5 bathrooms
6–11 Jul
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
4.97 out of 5 average rating, 199 reviews
Guest favourite
Apartment in Key West
EYW Getaway
2 bedrooms, 3 beds, 2 bathrooms
21–26 Jul
4.99 out of 5 average rating, 81 reviews
Guest favourite
Boat in Key West
Waterfront Boat Stay + Resort Amenities
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
4.93 out of 5 average rating, 30 reviews
Featured hotel
Hotel in Key West
La Pensione Inn Adults Only- Deluxe King
1 bedroom, 1 king bed, 1 bathroom
5–10 Jul
4.67 out of 5 average rating, 6 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
22–27 Aug
4.91 out of 5 average rating, 97 reviews
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
6 bedrooms, 6 beds, 6.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 26 reviews