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Search results; Over 1,000 homes in Key West

Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 private bathroom
17–22 Sept
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4.9 out of 5 average rating, 245 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
14–19 Sept
4.71 out of 5 average rating, 35 reviews
Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Apartment in Key West
Waterfront Condo Dock Pool Near Duval St
2 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.9 out of 5 average rating, 155 reviews
Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Key West
Casa Calypso 3bed3bath sleeps 8 beautiful decorate
3 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 40 reviews
Guest favourite
Home in Key West
Slice of Paradise
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds, 2.5 bathrooms
17–22 Sept
4.88 out of 5 average rating, 177 reviews
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Key West
Thompson Island USA !! Your Key West Retreat !!
9 bedrooms, 10 king beds, 6.5 bathrooms
14–19 Sept
4.79 out of 5 average rating, 105 reviews
Featured hotel
Hotel in Key West
Queen Room
1 bedroom, 1 queen bed, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Key West
Knowles Main House with Pool
5 bedrooms, 5 queen beds, 5 bathrooms
11–16 Oct
4.91 out of 5 average rating, 35 reviews
Luxe
Home in Key West
The Dreamside House at Lunara Bay
8 bedrooms, 8 king beds, 8.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 15 reviews
Superhost
Apartment in Key West
The Tahiti Suite | Updated Key West Condo w/ Pool!
2 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
New place to stay
Guest favourite
Flat in Key West
Oceanview condo w/pool, jacuzzi and tennis court
2 bedrooms, 4 beds, 2 bathrooms
21–28 Sept
4.93 out of 5 average rating, 14 reviews
Superhost
Apartment in Key West
Key West Paradise Condo w/ Pool, Hot Tub, Tennis
2 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
New place to stay
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
17–22 Sept
4.91 out of 5 average rating, 562 reviews
Top guest favourite
Home in Key West
Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
4 bedrooms, 5 beds, 4 bathrooms
19–24 Oct
4.91 out of 5 average rating, 239 reviews
Guest favourite
Apartment in Key West
Waterfront Dock Pool Pet Friendly Near Duval St
4 bedrooms, 9 beds, 4 bathrooms
12–17 Oct
4.88 out of 5 average rating, 229 reviews