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Search results; Over 1,000 homes in Key West

Boutique hotel in Key West
Parrot Key, Garden 2 Bedroom Suite w/ Living Room
2 bedrooms, 2 beds, 2 private bathrooms
10–15 Jul
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4.55 out of 5 average rating, 55 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds
3–8 Aug
New place to stay
Guest favourite
Boat in Key West
Glorious Floating Hotel Plus Amenities!
4 bedrooms, 4 beds
10–15 Jul
4.88 out of 5 average rating, 8 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
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds
3–8 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
8–13 Sept
5.0 out of 5 average rating, 16 reviews
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, 553 reviews
Superhost
Houseboat in Key West
Amazing houseboat with 2nd floor observation deck
1 bedroom, 2 beds
10–15 Jul
4.89 out of 5 average rating, 178 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds
22–27 Aug
4.97 out of 5 average rating, 201 reviews
Guest favourite
Boat in Key West
43' Classic Yacht Views, Pools, Duval Shuttle
2 bedrooms, 2 queen beds
12–17 Jul
4.83 out of 5 average rating, 24 reviews
Guest favourite
Boat in Key West
Luxurious 40' Sailing Yacht!
3 bedrooms, 4 beds
4–9 Aug
4.96 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
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
Featured hotel
Hotel in Key West
Superior Double Queen Pool/Balcony
1 bedroom, 2 queen beds
31 Jul – 5 Aug
4.86 out of 5 average rating, 14 reviews
Guest favourite
Apartment in Key West
Beach Club Ocean Front 2BR Condo
2 bedrooms, 3 beds
11–17 Jul
4.94 out of 5 average rating, 180 reviews
Hotel in Key West
Tropical King
1 bedroom, 1 bed
12–17 Jul
New place to stay
Guest favourite
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds
2–7 Aug
4.95 out of 5 average rating, 63 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Apartment in Key West
Tropical Heron Hideaway w/ Hot Tub + Pool
1 bedroom, 2 beds
7–12 Aug
4.93 out of 5 average rating, 114 reviews