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Search results; Over 1,000 homes in Key West

Guest favourite
Holiday home in Key West
Historic Cigar House. 3rd floor Suite W/Kitchen
1 bedroom, 2 beds, 1 private bathroom
6–11 Jul
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4.85 out of 5 average rating, 387 reviews
Top guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
1 bedroom, 1 bed
3–8 Aug
4.91 out of 5 average rating, 552 reviews
Guest favourite
Boat in Key West
Glorious Floating Hotel Plus Amenities!
4 bedrooms, 4 beds
4–9 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
16–21 Oct
4.97 out of 5 average rating, 200 reviews
Hotel in Key West
Minutes to Duval + Free Breakfast. Newly Renovated
1 bedroom, 2 queen beds
5–10 Jul
4.72 out of 5 average rating, 123 reviews
Guest favourite
Boat in Key West
43' Classic Yacht Views, Pools, Duval Shuttle
2 bedrooms, 2 queen beds
17–22 Jul
4.83 out of 5 average rating, 24 reviews
Guest favourite
Boat in Key West
Off Grid HouseBoat "Shanty Pineapple Key West"
1 bed
12–17 Jul
4.95 out of 5 average rating, 88 reviews
Featured hotel
Hotel in Key West
Superior King Pool/Balcony
1 bedroom, 1 king bed
5–10 Jul
4.7 out of 5 average rating, 10 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds
12–17 Jul
4.88 out of 5 average rating, 176 reviews
Top guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
3 bedrooms, 3 beds
27 Jul – 1 Aug
5.0 out of 5 average rating, 15 reviews
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds
13–18 Jul
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds
2–7 Aug
5.0 out of 5 average rating, 15 reviews
Guest favourite
Boat in Key West
Luxurious 40' Sailing Yacht!
3 bedrooms, 4 beds
3–8 Aug
4.96 out of 5 average rating, 24 reviews
Guest favourite
Boat in Key West
Waterfront Boat Stay + Resort Amenities
1 bedroom, 2 beds
19–24 Jul
4.93 out of 5 average rating, 30 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds
12–17 Jul
New place to stay
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Cudjoe Key
Ocean's Edge VO Pad Boards, Kayak, Bikes-30 min KW
2 bedrooms, 4 beds
27 Aug – 1 Sept
4.97 out of 5 average rating, 86 reviews
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds
9–14 Jul
4.86 out of 5 average rating, 42 reviews
Guest favourite
Boat in Key West
Sentient Waters: 63’ Boat, Free Snorkel Gear, etc.
2 bedrooms, 3 beds
15–20 Aug
4.87 out of 5 average rating, 30 reviews