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Search results; Over 1,000 homes in Key West

Guest favourite
Cottage in Key West
Stay at Hidden Treasure for a relaxing vacation!
2 bedrooms, 3 beds, 2 private bathrooms
31 Aug – 5 Sept
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4.74 out of 5 average rating, 100 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
4.91 out of 5 average rating, 554 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
3–8 Aug
New place to stay
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
6–11 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 16 reviews
Superhost
Houseboat in Key West
Amazing houseboat with 2nd floor observation deck
1 bedroom, 2 beds, 1 bathroom
13–18 Jul
4.89 out of 5 average rating, 178 reviews
Guest favourite
Boat in Key West
Glorious Floating Hotel Plus Amenities!
4 bedrooms, 4 beds, 4 bathrooms
18–23 Jul
4.88 out of 5 average rating, 8 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.97 out of 5 average rating, 201 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds, 2.5 bathrooms
14–19 Jul
4.88 out of 5 average rating, 176 reviews
Guest favourite
Flat in Key West
Luxury Designer Estate - Lunara Bay Collection
6 bedrooms, 8 beds, 6.5 bathrooms
17–22 Jul
5.0 out of 5 average rating, 9 reviews
Guest favourite
Boat in Key West
Off Grid HouseBoat "Shanty Pineapple Key West"
1 bed, 1 bathroom
20–25 Jul
4.95 out of 5 average rating, 88 reviews
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Awai's Floating Villa
2 bedrooms, 2 queen beds, 2 bathrooms
13–18 Jul
4.93 out of 5 average rating, 84 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 15 reviews
Featured hotel
Hotel in Key West
Pensione Inn Adults Only – Cortez Suite
1 bedroom, 1 king bed, 1 bathroom
19–24 Jul
Guest favourite
Boat in Key West
43' Classic Yacht Views, Pools, Duval Shuttle
2 bedrooms, 2 queen beds, 1.5 bathrooms
13–18 Jul
4.83 out of 5 average rating, 24 reviews
Guest favourite
Home in Key West
Real World MTV House Key West - 18 to 22 guests
10 bedrooms, 13 beds, 5.5 bathrooms
13–18 Jul
4.86 out of 5 average rating, 123 reviews
Guest favourite
Boat in Key West
Luxurious 40' Sailing Yacht!
3 bedrooms, 4 beds, 2 bathrooms
4–9 Aug
4.96 out of 5 average rating, 24 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 5 reviews
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
2–7 Aug
4.86 out of 5 average rating, 42 reviews