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Search results; Over 1,000 homes in Key West

Guest favourite
Holiday home in Key West
Historic Cigar House. 3rd floor Suite W/Kitchen
1 bedroom, 2 beds, 1 private bathroom
14–19 Sept
,
4.85 out of 5 average rating, 392 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
18–23 Aug
4.91 out of 5 average rating, 557 reviews
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds
26 Sept – 1 Oct
4.83 out of 5 average rating, 111 reviews
Guest favourite
Apartment in Key West
Waterfront Dock Pool Near Duval St Penthouse
4 bedrooms, 9 beds
16–21 Aug
4.91 out of 5 average rating, 211 reviews
Top guest favourite
Apartment in Key West
Boat Slip - Waterfront Condo - Key West Pool
2 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds
30 Aug – 4 Sept
4.86 out of 5 average rating, 43 reviews
Superhost
Home in Marathon
*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!
4 bedrooms, 5 beds
11–18 Sept
New place to stay
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds
5–10 Oct
4.91 out of 5 average rating, 102 reviews
Top guest favourite
Home in Marathon
Waterfront 6BR Luxury Retreat w/ Pool & Dock
6 bedrooms, 10 beds
3–10 Oct
5.0 out of 5 average rating, 31 reviews
Superhost
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
2 bedrooms, 2 queen beds
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 4 reviews
Townhouse in Key West
The Lighthouse Group Suite
4 bedrooms, 6 beds
11–16 Oct
4.96 out of 5 average rating, 27 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds
20–25 Aug
4.56 out of 5 average rating, 25 reviews
Home in Marathon
Marlin House | Waterfront Pool Home Near Marina
2 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 4 reviews
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
6 bedrooms, 6 beds
17–22 Aug
5.0 out of 5 average rating, 28 reviews
Featured hotel
Room in Key West
One king bed
13–18 Aug
New place to stay
Guest favourite
Home in Key West
Waterfront Home in Key Cove Landings
4 bedrooms, 6 beds
15–20 Aug
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
2 bedrooms, 4 beds
24–29 Aug
4.86 out of 5 average rating, 7 reviews