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Search results; Over 1,000 homes in Key West

Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 private bathroom
17–22 Sept
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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
17–22 Sept
4.88 out of 5 average rating, 177 reviews
Featured hotel
Room in Key West
Classic Double Queen City/Balcony
2 queen beds, 1 bathroom
12–17 Sept
4.81 out of 5 average rating, 72 reviews
Top guest favourite
Home in Key West
Casa Cristol - Truman Annex
3 bedrooms, 3 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 21 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, 34 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, 17 reviews
Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 22 reviews
Featured hotel
Rooms in Key West
Two bedrooms bi-level garden view suite
2 bedrooms, 1 bathroom
12–17 Sept
4.82 out of 5 average rating, 22 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
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
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
13–18 Sept
4.87 out of 5 average rating, 45 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
12–17 Sept
4.71 out of 5 average rating, 35 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
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
Houseboat in Key West
Tiki Suites~The Grand Tiki~Private Water Stay
1 bedroom, 1 bed, 1 bathroom
17–22 Sept
4.92 out of 5 average rating, 362 reviews
Guest favourite
Home in Key West
Old Town Key West Escape - The “Eyebrow Saltbox”
3 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.88 out of 5 average rating, 16 reviews
Guest favourite
Home in Key West
MERMAID COVE- Funky Getaway on Duval
4 bedrooms, 5 beds, 4 bathrooms
22–27 Sept
4.9 out of 5 average rating, 250 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