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Search results; Over 1,000 homes in Key West

Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 private bathroom
10–15 Sept
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4.9 out of 5 average rating, 245 reviews
Top guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds, 3 bathrooms
11–16 Oct
Guest favourite
Home in Key West
Gone Coastal 2
3 bedrooms, 5 beds, 2.5 bathrooms
25–30 Sept
4.93 out of 5 average rating, 128 reviews
Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds, 2 bathrooms
28 Sept – 3 Oct
New place to stay
Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Key West
Casa Calypso 3bed3bath sleeps 8 beautiful decorate
3 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 39 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
13–18 Sept
4.84 out of 5 average rating, 31 reviews
Guest favourite
Apartment in Key West
Parking & Shared Pool - Casa Key West
3 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
4.71 out of 5 average rating, 173 reviews
Top guest favourite
Home in Key West
Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
4 bedrooms, 5 beds, 4 bathrooms
19–24 Oct
4.91 out of 5 average rating, 238 reviews
Guest favourite
Apartment in Key West
EYW Getaway
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 86 reviews
Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
5.0 out of 5 average rating, 41 reviews
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
6 bedrooms, 6 beds, 6.5 bathrooms
15–20 Oct
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Key West
Knowles Main House with Pool
5 bedrooms, 5 queen beds, 5 bathrooms
11–16 Oct
4.91 out of 5 average rating, 35 reviews
Guest favourite
Apartment in Key West
Penthouse Waterfront Dock Pool Condo Near Duval St
4 bedrooms, 11 beds, 4 bathrooms
13–18 Oct
4.9 out of 5 average rating, 265 reviews
Top guest favourite
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds, 3.5 bathrooms
3–10 Oct
5.0 out of 5 average rating, 5 reviews
Luxe
Home in Key West
Floralee House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
18–23 Oct
4.95 out of 5 average rating, 40 reviews
Guest favourite
Flat in Key West
Castaway Cove: Pet-friendly 2/2 condo near beach!
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.89 out of 5 average rating, 120 reviews