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Search results; Over 1,000 homes in Key West

Top guest favourite
Flat in Key West
Key West Beachside 1400sf, 2 Bedroom Condo
2 bedrooms, 2 beds, 2 private bathrooms
26–31 Aug
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4.91 out of 5 average rating, 167 reviews
Featured hotel
Room in Key West
High floor island view two queen beds
2 queen beds, 1 bathroom
15–20 Aug
New place to stay
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
30 Aug – 4 Sept
4.86 out of 5 average rating, 43 reviews
Guest favourite
Apartment in Key West
Waterfront Dock Pool Near Duval St Penthouse
4 bedrooms, 9 beds, 4 bathrooms
16–21 Aug
4.91 out of 5 average rating, 211 reviews
Guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
20–25 Aug
4.56 out of 5 average rating, 25 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 558 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
4.91 out of 5 average rating, 102 reviews
Top guest favourite
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
2 bedrooms, 4 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 7 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
16–21 Aug
4.8 out of 5 average rating, 20 reviews
Top guest favourite
Home in Marathon
Waterfront 6BR Luxury Retreat w/ Pool & Dock
6 bedrooms, 10 beds, 5 bathrooms
3–10 Oct
5.0 out of 5 average rating, 31 reviews
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Away Awai Floating Vill
2 bedrooms, 2 queen beds, 2 bathrooms
29 Aug – 3 Sept
4.93 out of 5 average rating, 85 reviews
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
6 bedrooms, 6 beds, 6.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 28 reviews
Luxe
Home in Key West
Floralee House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 39 reviews
Guest favourite
Apartment in Key West
Waterfront Condo Dock Pool Downtown Near Duval
2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.91 out of 5 average rating, 276 reviews
Guest favourite
Home in Key West
Waterfront Home in Key Cove Landings
4 bedrooms, 6 beds, 3 bathrooms
17–22 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, 2 bathrooms
24–29 Aug
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
24–31 Oct
5.0 out of 5 average rating, 87 reviews
Top guest favourite
Flat in Key West
Newly Renovated 2/2 Bath Condo, with shared pool
2 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
4.99 out of 5 average rating, 84 reviews