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Search results; Over 1,000 homes in Key West

Guest favourite
Apartment in Key West
Tropical Escape at Sunrise
2 bedrooms, 3 beds, 2 shared bathrooms
13–18 Jul
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4.91 out of 5 average rating, 179 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
New place to stay, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
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
9–14 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
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
4.91 out of 5 average rating, 553 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Superhost
Houseboat in Key West
Amazing houseboat with 2nd floor observation deck
4.89 out of 5 average rating, 178 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Jul
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
Top guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
5.0 out of 5 average rating, 16 reviews, 3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
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
12–17 Jul
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
4.97 out of 5 average rating, 201 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
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
4–9 Aug
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
Featured hotel
Hotel in Key West
Superior Double Queen Pool/Balcony
4.85 out of 5 average rating, 13 reviews, 1 bedroom, 1 bathroom
31 Jul – 5 Aug
Guest favourite
Apartment in Key West
Beach Club Ocean Front 2BR Condo
4.94 out of 5 average rating, 180 reviews, 2 bedrooms, 3 beds, 2.5 bathrooms
10–16 Jul
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
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 1 bathroom
31 Jul – 5 Aug
Hotel in Key West
Tropical King
New place to stay, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Home in Key West
Casa Cristol - Truman Annex
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 3 beds, 3 bathrooms
10–15 Aug
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