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Search results; Over 1,000 homes in Key West

Guest favourite
Apartment in Key West
Condo de Paradise/Salt Water Pool/Boat Dock
2 bedrooms, 3 beds, 2 private bathrooms
10–17 Sept
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4.96 out of 5 average rating, 47 reviews
Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 41 reviews
Featured hotel
Room in Key West
Classic Double Queen City/Balcony
2 queen beds, 1 bathroom
13–18 Sept
4.81 out of 5 average rating, 72 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, 32 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, 561 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds, 2.5 bathrooms
11–16 Sept
4.88 out of 5 average rating, 177 reviews
Guest favourite
Boat in Key West
*August/September specials* off Grid Boat Key West
1 queen bed, 1 bathroom
10–15 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
13–18 Sept
4.85 out of 5 average rating, 33 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 22 reviews
Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Sept
5.0 out of 5 average rating, 3 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
10–15 Sept
4.92 out of 5 average rating, 362 reviews
Featured hotel
Rooms in Key West
Two bedrooms bi-level garden view suite
2 bedrooms, 1 bathroom
28 Sept – 3 Oct
4.82 out of 5 average rating, 22 reviews
Top guest favourite
Home in Key West
Poolside Paradise/3Brs, 2.5 bath/Pvt. Pool/Spa
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 36 reviews
Guest favourite
Boat in Key West
Sailboat Retreat | Resort Amenities
1 bedroom, 1 queen bed, 2 bathrooms
10–15 Sept
4.93 out of 5 average rating, 55 reviews
Featured hotel
Room in Key West
Havana king room
2 king beds, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Boat in Key West
Luxurious 40' Sailing Yacht!
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 25 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
Guest favourite
Boat in Key West
“The Easy Way” Comfy, Practical, Convenient
1 bedroom, 1 king bed, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 24 reviews