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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
1 bedroom, 1 bed, 1 bathroom
3–8 Aug
4.91 out of 5 average rating, 553 reviews
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
2–7 Aug
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
27 Aug – 1 Sept
4.83 out of 5 average rating, 111 reviews
Superhost
Flat in Key West
Turtle Nest Condo + Pool
1 bedroom, 1 king bed, 1 bathroom
19–24 Jul
New place to stay
Luxe
Home in Marathon
The Pearl at SeaGlass Cove Waterfront Luxury Home!
5 bedrooms, 5 beds, 4.5 bathrooms
9–16 Jul
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
2 bedrooms, 2 queen beds, 2 bathrooms
7–12 Jul
Luxe
Home in Key West
Spindrift House at Lunara Bay
4 bedrooms, 7 beds, 4 bathrooms
14–19 Aug
4.85 out of 5 average rating, 95 reviews
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
9–14 Jul
4.86 out of 5 average rating, 42 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
4.56 out of 5 average rating, 25 reviews
Top guest favourite
Home in Marathon
Tropical Keys Retreat | Pool | Hot Tub | Cinema
3 bedrooms, 4 beds, 3 bathrooms
11–18 Jul
5.0 out of 5 average rating, 76 reviews
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds, 4.5 bathrooms
7–12 Jul
5.0 out of 5 average rating, 21 reviews
Home in Marathon
NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip
5 bedrooms, 6 beds, 4 bathrooms
22–29 Aug
New place to stay
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Key West
3 Bedroom Home - Perfect Location & Private Pool
3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 36 reviews
Home in Marathon
Special-New Oceanfront Home-5Ksf under $1K a nite!
5 bedrooms, 5 beds, 4.5 bathrooms
12–19 Jul
New place to stay
Featured hotel
Hotel in Key West
Classic King City/Balcony
1 bedroom, 1 king bed, 1 bathroom
12–17 Jul
4.89 out of 5 average rating, 19 reviews
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
6 bedrooms, 6 beds, 6.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 26 reviews