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Search results; Over 1,000 homes

Guest favourite
Room in Key West
Beach's Paradise
1 bedroom, 1 bed, 1 private bathroom
10–15 Mar
,
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Home in Key West
William Skelton Home - Sleeps 16 just off Duval St
6 bedrooms, 10 beds, 4 bathrooms
25–30 Oct
4.98 out of 5 average rating, 60 reviews
Guest favourite
Home in Key West
Waterlane House at Lunara Bay
4 bedrooms, 7 beds, 4.5 bathrooms
27 Sept – 2 Oct
4.85 out of 5 average rating, 112 reviews
Guest favourite
Home in Key West
Gone Coastal 2
3 bedrooms, 5 beds, 2.5 bathrooms
25–30 Sept
4.93 out of 5 average rating, 130 reviews
Guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds, 2 bathrooms
7–12 Oct
5.0 out of 5 average rating, 9 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
15–20 Sept
4.71 out of 5 average rating, 35 reviews
Guest favourite
Home in Key West
Thompson Island USA !! Your Key West Retreat !!
9 bedrooms, 10 king beds, 6.5 bathrooms
15–20 Sept
4.79 out of 5 average rating, 105 reviews
Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds, 3 bathrooms
18–23 Sept
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Apartment in Key West
Gorgeous Ocean View in Paradise, Close to Key West
3 bedrooms, 4 beds, 2 bathrooms
3–8 Oct
4.99 out of 5 average rating, 140 reviews
Guest favourite
Boat in Key West
Glorious Floating Hotel Plus Amenities!
4 bedrooms, 4 beds, 4 bathrooms
15–20 Sept
4.91 out of 5 average rating, 11 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
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
4.91 out of 5 average rating, 562 reviews
Guest favourite
Flat in Key West
Castaway Cove: Pet-friendly 2/2 condo near beach!
2 bedrooms, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.89 out of 5 average rating, 120 reviews
Luxe
Home in Key West
The Windrose Estate at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
27 Sept – 2 Oct
4.9 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Key West
Newly Renovated 2/2 Bath Condo, with shared pool
2 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.99 out of 5 average rating, 87 reviews
Guest favourite
Home in Key West
Near Key West | Bikes | Parking | Heated Pool
2 bedrooms, 3 beds, 2.5 bathrooms
18–23 Sept
4.74 out of 5 average rating, 147 reviews
Guest favourite
Apartment in Key West
Fully renovated 2/2 bath condo w/ shared pool!
2 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
4.95 out of 5 average rating, 212 reviews
Top guest favourite
Home in Key West
Casa Capri 3 bed 3 bath sleeps 8 tropical decorate
3 bedrooms, 4 beds, 3 bathrooms
15–20 Sept
4.97 out of 5 average rating, 62 reviews
Guest favourite
Boat in Key West
Luxurious 40' Sailing Yacht!
3 bedrooms, 4 beds, 2 bathrooms
23–28 Sept
4.96 out of 5 average rating, 25 reviews