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Search results; Over 1,000 homes in Key West

Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Private Water Stay
Waterfront, Ocean views
27 Jul – 1 Aug
4.91 out of 5 average rating, 554 reviews
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
7 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 38 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds
30 Sept – 5 Oct
New place to stay
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
Waterfront
6–11 Aug
5.0 out of 5 average rating, 4 reviews
Hotel in Key West
Tropical King
1 bed
19–24 Jul
New place to stay
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
4 beds
10–17 Aug
5.0 out of 5 average rating, 9 reviews
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
4 beds
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
5 beds
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Luxe
Home in Key West
The Seagate Estate at Lunara Bay
Waterfront
16–21 Aug
4.8 out of 5 average rating, 59 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
On the beach, Kayak
2–7 Aug
4.56 out of 5 average rating, 25 reviews
Superhost
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
Waterfront
20–25 Jul
Top guest favourite
Home in Marathon
Sombrero Sunset-Marathon 7BR 6BA Waterfront Pool
8 beds
29 Aug – 5 Sept
4.97 out of 5 average rating, 35 reviews
Luxe
Home in Key West
The Greenmoor House at Lunara Bay
Waterfront, Boat berth
1–6 Aug
5.0 out of 5 average rating, 10 reviews
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
Boat, Waterskis
2–7 Aug
5.0 out of 5 average rating, 26 reviews
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
Waterfront
17–22 Jul
4.83 out of 5 average rating, 23 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
Waterfront
22–27 Aug
4.91 out of 5 average rating, 97 reviews
Top guest favourite
Home in Key West
Family House, 2 K BR's, Private Spa/Deck, 2 pools.
3 beds
7–12 Aug
4.92 out of 5 average rating, 323 reviews
Guest favourite
Townhouse in Marathon
Beautiful View! 4BR 3 BA 32FT Dock, Cabana Club!
5 beds
30 Aug – 4 Sept
4.93 out of 5 average rating, 29 reviews