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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
17–22 Sept
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4.83 out of 5 average rating, 23 reviews
Featured hotel
Hotel in Key West
Classic Double Queen City/Balcony
1 bedroom, 2 queen beds, 1 bathroom
14–19 Sept
4.81 out of 5 average rating, 74 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds, 2.5 bathrooms
17–22 Sept
4.88 out of 5 average rating, 177 reviews
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, 18 reviews
Top guest favourite
Home in Key West
Casa Cristol - Truman Annex
3 bedrooms, 3 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds, 3 bathrooms
17–22 Sept
5.0 out of 5 average rating, 41 reviews
Featured hotel
Hotel in Key West
Two bedroom bi-level pool view suite
2 bedrooms, 1 bathroom
14–19 Sept
4.9 out of 5 average rating, 39 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
14–19 Sept
4.71 out of 5 average rating, 35 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
17–22 Sept
4.91 out of 5 average rating, 562 reviews
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds, 4.5 bathrooms
20–25 Sept
4.86 out of 5 average rating, 35 reviews
Guest favourite
Boat in Key West
*Off Grid Boat Key West
1 queen bed, 1 bathroom
14–19 Sept
4.96 out of 5 average rating, 95 reviews
Superhost
Rooms in Key West
Duval St. Duplex w/Balcony W/ Parking (Adult Only)
2 bedrooms, 4 queen beds, 1 bathroom
28 Sept – 3 Oct
4.86 out of 5 average rating, 324 reviews
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
26–31 Oct
4.87 out of 5 average rating, 45 reviews
Featured hotel
Hotel in Key West
Havana king room
1 bedroom, 2 king beds, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 bathroom
17–22 Sept
4.9 out of 5 average rating, 245 reviews
Hotel in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 bedroom, 1 king bed, 1 bathroom
14–19 Sept
4.74 out of 5 average rating, 23 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Boat in Key West
Amazing 4 Bdrm, 4 Bath Catamaran- Sleeps up to 8
4 bedrooms, 4 beds, 4 bathrooms
27 Sept – 2 Oct
4.89 out of 5 average rating, 37 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, 63 reviews