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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
10–15 Sept
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4.9 out of 5 average rating, 245 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
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
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, 16 reviews
Guest favourite
Home in Key West
Paradise found
3 bedrooms, 4 beds
29 Sept – 4 Oct
4.94 out of 5 average rating, 158 reviews
Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds
28 Sept – 3 Oct
New place to stay
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds
11–16 Oct
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, 40 reviews
Guest favourite
Home in Key West
MERMAID COVE- Funky Getaway on Duval
4 bedrooms, 5 beds
22–27 Sept
4.9 out of 5 average rating, 250 reviews
Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds
11–16 Sept
5.0 out of 5 average rating, 41 reviews
Guest favourite
Home in Key West
Harbor House Penthouse- B
4 bedrooms, 5 beds
8–13 Sept
4.84 out of 5 average rating, 38 reviews
Top guest favourite
Home in Key West
Pilar House
3 bedrooms, 3 beds
13–18 Dec
4.96 out of 5 average rating, 47 reviews
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
6 bedrooms, 6 beds
15–20 Oct
5.0 out of 5 average rating, 28 reviews
Guest favourite
Apartment in Key West
Penthouse Waterfront Dock Pool Condo Near Duval St
4 bedrooms, 11 beds
13–18 Oct
4.9 out of 5 average rating, 265 reviews
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
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
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds
9–14 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Apartment in Key West
Coastline Comfort
2 bedrooms, 4 beds
3–8 Oct
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
13–18 Sept
4.79 out of 5 average rating, 105 reviews