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Search results; Over 1,000 homes in Key West

Guest favourite
Hotel room in Key West
The Sanchez House Room #1
1 bedroom, 1 bed, 1 shared bathroom
29 Sept – 4 Oct
,
4.86 out of 5 average rating, 672 reviews
Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds
12–17 Sept
5.0 out of 5 average rating, 41 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
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds
13–18 Sept
4.84 out of 5 average rating, 32 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
17–22 Sept
4.91 out of 5 average rating, 561 reviews
Guest favourite
Boat in Key West
*August/September specials* off Grid Boat Key West
1 queen bed
9–14 Sept
4.96 out of 5 average rating, 95 reviews
Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds
10–15 Sept
4.9 out of 5 average rating, 245 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds
10–15 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Houseboat in Key West
Tiki Suites~The Grand Tiki~Private Water Stay
1 bedroom, 1 bed
9–14 Sept
4.92 out of 5 average rating, 362 reviews
Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds
10–15 Sept
4.88 out of 5 average rating, 177 reviews
Top guest favourite
Home in Key West
Casa Cristol - Truman Annex
3 bedrooms, 3 beds
13–18 Sept
5.0 out of 5 average rating, 21 reviews
Featured hotel
Rooms in Key West
Two bedrooms bi-level garden view suite
2 bedrooms
9–14 Sept
4.82 out of 5 average rating, 22 reviews
Guest favourite
Boat in Key West
Sailboat Retreat | Resort Amenities
1 bedroom, 1 queen bed
9–14 Sept
4.93 out of 5 average rating, 55 reviews
Guest favourite
Boat in Key West
Luxurious 40' Sailing Yacht!
3 bedrooms, 4 beds
13–18 Sept
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
3 bedrooms, 3 beds
26 Sept – 1 Oct
4.81 out of 5 average rating, 27 reviews
Top guest favourite
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds
3–10 Oct
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Key West
Real World MTV House Key West - 18 to 22 guests
10 bedrooms, 13 beds
16–21 Sept
4.87 out of 5 average rating, 126 reviews