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Search results; Over 1,000 homes in Key West

Top guest favourite
Apartment in Key West
Waterfront Condo | Pool, Dock, Parking, Sleeps 8
2 bedrooms, 4 beds, 2 private bathrooms
24–29 Sept
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4.88 out of 5 average rating, 304 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
13–18 Sept
4.83 out of 5 average rating, 30 reviews
Featured hotel
Room in Key West
Hearing Accessible Classic King City/Balcony
1 king bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Key West
Paradise found
3 bedrooms, 4 beds, 3 bathrooms
29 Sept – 4 Oct
4.94 out of 5 average rating, 158 reviews
Top guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds, 3 bathrooms
11–16 Oct
Top guest favourite
Home in Key West
Pilar House
3 bedrooms, 3 beds, 2 bathrooms
13–18 Dec
4.96 out of 5 average rating, 46 reviews
Guest favourite
Apartment in Key West
Fully renovated 2/2 bath condo w/ shared pool!
2 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.95 out of 5 average rating, 211 reviews
Superhost
Home in Key West
Private Parking, Heated Pool - Sweet Caroline
2 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
4.57 out of 5 average rating, 136 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 561 reviews
Top guest favourite
Boutique hotel in Key West
Mallory House Room #3
1 bedroom, 1 queen bed, 1 bathroom
14–19 Sept
4.89 out of 5 average rating, 526 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 21 reviews
Luxe
Home in Key West
Floralee House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
18–23 Oct
4.95 out of 5 average rating, 40 reviews
Guest favourite
Home in Key West
Thompson Island USA !! Your Key West Retreat !!
9 bedrooms, 10 king beds, 6.5 bathrooms
6–11 Sept
4.79 out of 5 average rating, 105 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, 14 reviews
Guest favourite
Apartment in Key West
EYW Getaway
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 86 reviews
Superhost
Flat in Key West
Turtle Nest Condo + Pool • 2nd Floor
1 bedroom, 1 king bed, 1 bathroom
18–23 Sept
4.7 out of 5 average rating, 10 reviews
Superhost
Villa in Marathon
New Aqua Lodge 2Beds 1 Bath with Full Kitchens
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.86 out of 5 average rating, 610 reviews
Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
5.0 out of 5 average rating, 41 reviews