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Search results; Over 1,000 homes in Key West

Superhost
Hotel in Key West
Luxurious Stay | Snorkeling. Outdoor Pool
1 bedroom, 1 bed, 1 private bathroom
27 Sept – 2 Oct
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4.67 out of 5 average rating, 54 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
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
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
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
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
Waterfront Boat Stay + Resort Amenities
1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.94 out of 5 average rating, 36 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
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
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.96 out of 5 average rating, 212 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
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
Featured hotel
Hotel in Key West
Two bedrooms bi-level garden view suite
2 bedrooms, 1 bathroom
28 Sept – 3 Oct
4.83 out of 5 average rating, 24 reviews
Luxe
Home in Key West
Catchlight House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
11–16 Oct
4.98 out of 5 average rating, 42 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
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 bathroom
19–24 Sept
4.9 out of 5 average rating, 245 reviews
Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
17–22 Oct
5.0 out of 5 average rating, 18 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, 6 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