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Search results; Over 1,000 homes in Key West

Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds
13–18 Sept
4.86 out of 5 average rating, 29 reviews
Top guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Boat in Key West
“The Easy Way” Comfy, Practical, Convenient
1 bedroom, 1 king bed
8–13 Sept
5.0 out of 5 average rating, 24 reviews
Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds
9–14 Oct
New place to stay
Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Apartment in Key West
Parking & Shared Pool - Casa Key West
3 bedrooms, 5 beds
14–19 Sept
4.71 out of 5 average rating, 173 reviews
Guest favourite
Home in Key West
Casa Calypso 3bed3bath sleeps 8 beautiful decorate
3 bedrooms, 5 beds
14–19 Sept
5.0 out of 5 average rating, 39 reviews
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds
11–16 Oct
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
13–18 Sept
4.91 out of 5 average rating, 561 reviews
Featured hotel
Room in Key West
Accessible Classic Double Queen City/Balcony
2 queen beds
20–25 Sept
4.71 out of 5 average rating, 7 reviews
Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds
9–14 Sept
5.0 out of 5 average rating, 41 reviews
Guest favourite
Boat in Key West
Luxurious 40' Sailing Yacht!
3 bedrooms, 4 beds
6–11 Sept
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds
8–13 Sept
5.0 out of 5 average rating, 21 reviews
Guest favourite
Flat in Key West
Casa Caribe 2bed2bath sleeps 6 beautiful decorated
2 bedrooms, 3 beds
8–13 Sept
4.96 out of 5 average rating, 28 reviews
Guest favourite
Home in Key West
Paradise found
3 bedrooms, 4 beds
7–12 Sept
4.94 out of 5 average rating, 157 reviews
Top guest favourite
Home in Key West
Pilar House
3 bedrooms, 3 beds
13–18 Dec
4.96 out of 5 average rating, 46 reviews
Guest favourite
Home in Key West
Thompson Island USA !! Your Key West Retreat !!
9 bedrooms, 10 king beds
6–11 Sept
4.79 out of 5 average rating, 105 reviews
Top guest favourite
Flat in Key West
Newly Renovated 2/2 Bath Condo, with shared pool
2 bedrooms, 3 beds
21–26 Sept
4.99 out of 5 average rating, 87 reviews