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Search results; Over 1,000 homes in Key West

Top guest favourite
Boutique hotel in Key West
Mallory House Room #3
1 bedroom, 1 bed, 1 shared bathroom
20–25 Sept
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4.89 out of 5 average rating, 528 reviews
Featured hotel
Hotel in Key West
Pensione Inn Adults Only – Cortez Suite
1 bedroom, 1 king bed, 1 bathroom
25–30 Sept
5.0 out of 5 average rating, 7 reviews
Featured hotel
Hotel in Key West
Two bedroom bi-level pool view suite
2 bedrooms, 1 bathroom
15–20 Sept
4.9 out of 5 average rating, 39 reviews
Featured hotel
Hotel in Key West
Havana king room
1 bedroom, 2 king beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 4 reviews
Featured hotel
Hotel in Key West
King city single room
1 bedroom, 1 king bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 25 reviews
Featured hotel
Hotel in Key West
Havana king accessible
1 bedroom, 1 king bed, 1 bathroom
15–20 Sept
Featured hotel
Hotel in Key West
Queen Room
1 bedroom, 1 queen bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 17 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
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds, 3 bathrooms
18–23 Sept
5.0 out of 5 average rating, 41 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
19–24 Sept
4.91 out of 5 average rating, 562 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
15–20 Sept
4.71 out of 5 average rating, 35 reviews
Guest favourite
Boat in Key West
*Off Grid Boat Key West
1 queen bed, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 95 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
Hotel in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 bedroom, 1 king bed, 1 bathroom
15–20 Sept
4.72 out of 5 average rating, 25 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
Home in Key West
Real World MTV House Key West - 18 to 22 guests
10 bedrooms, 13 beds, 5.5 bathrooms
16–21 Sept
4.87 out of 5 average rating, 126 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
Guest favourite
Houseboat in Key West
Tiki Suites~The Grand Tiki~Private Water Stay
1 bedroom, 1 bed, 1 bathroom
19–24 Sept
4.92 out of 5 average rating, 362 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