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Search results; Over 1,000 homes in Key West

Top guest favourite
Home in Key West
Lennon's Lodge, Luxury Accommodations for up to 6!
2 bedrooms, 3 beds, 1 private bathroom
6–11 Jul
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4.96 out of 5 average rating, 248 reviews
Top guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
4.91 out of 5 average rating, 552 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
4.97 out of 5 average rating, 200 reviews, 2 bedrooms, 3 beds, 2 bathrooms
16–21 Oct
Guest favourite
Boat in Key West
Glorious Floating Hotel Plus Amenities!
4.88 out of 5 average rating, 8 reviews, 4 bedrooms, 4 beds, 4 bathrooms
4–9 Jul
Hotel in Key West
Minutes to Duval + Free Breakfast. Newly Renovated
4.72 out of 5 average rating, 123 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Jul
Featured hotel
Hotel in Key West
Superior King Pool/Balcony
4.7 out of 5 average rating, 10 reviews, 1 bedroom, 1 bathroom
5–10 Jul
Guest favourite
Boat in Key West
43' Classic Yacht Views, Pools, Duval Shuttle
4.83 out of 5 average rating, 24 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
17–22 Jul
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
4.88 out of 5 average rating, 176 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
12–17 Jul
Guest favourite
Boat in Key West
Off Grid HouseBoat "Shanty Pineapple Key West"
4.95 out of 5 average rating, 88 reviews, 1 bed, 1 bathroom
12–17 Jul
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 beds, 2 bathrooms
13–18 Jul
Top guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
5.0 out of 5 average rating, 15 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Jul – 1 Aug
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Aug
Guest favourite
Boat in Key West
Waterfront Boat Stay + Resort Amenities
4.93 out of 5 average rating, 30 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Guest favourite
Boat in Key West
Luxurious 40' Sailing Yacht!
4.96 out of 5 average rating, 24 reviews, 3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
New place to stay, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Guest favourite
Boat in Key West
Sentient Waters: 63’ Boat, Free Snorkel Gear, etc.
4.87 out of 5 average rating, 30 reviews, 2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
Luxe
Home in Key West
Altair House at Lunara Bay
4.86 out of 5 average rating, 42 reviews, 6 bedrooms, 9 beds, 6.5 bathrooms
9–14 Jul
Flat in Key West
Beautiful Corner Condo Overlooking Pool
2 bedrooms, 4 beds, 2 bathrooms
8–13 Aug