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Search results; Over 1,000 homes in Key West

Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 private bathroom
18–23 Aug
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4.91 out of 5 average rating, 555 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
5.0 out of 5 average rating, 85 reviews, 4 bedrooms, 8 beds, 3 bathrooms
15–22 Aug
Guest favourite
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
5.0 out of 5 average rating, 9 reviews, 2 queen beds, 1 bathroom
30 Sept – 5 Oct
Guest favourite
Home in Key West
Luxury Retreat-Old Town; Pool, Parking, Near Duval
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4.81 out of 5 average rating, 26 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
1–6 Aug
Luxe
Home in Key West
The Seagate Estate at Lunara Bay
4.8 out of 5 average rating, 61 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
16–21 Aug
Flat in Key West
Apartment in Key west
New place to stay, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Away Awai Floating Vill
4.93 out of 5 average rating, 84 reviews, 2 bedrooms, 2 beds, 2 bathrooms
4–9 Aug
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 100 reviews, 3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
Guest favourite
Boat in Key West
Luxurious 40' Sailing Yacht!
4.96 out of 5 average rating, 24 reviews, 3 bedrooms, 4 beds, 2 bathrooms
4–9 Aug
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Home in Marathon
New Oceanfront•Sunrise Views•Pool/hot tub•Dock
5.0 out of 5 average rating, 16 reviews, 5 bedrooms, 10 beds, 6 bathrooms
15–22 Aug
Luxe
Home in Key West
The Greenmoor House at Lunara Bay
5.0 out of 5 average rating, 11 reviews, 6 bedrooms, 9 beds, 6.5 bathrooms
9–14 Aug
Guest favourite
Houseboat in Key West
Tiki Suites~The Grand Tiki~Private Water Stay
4.92 out of 5 average rating, 356 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Home in Marathon
4BR Gulffront Dog Friendly | Pool | Dock | Deck
4.71 out of 5 average rating, 7 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
16–23 Aug
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
4.83 out of 5 average rating, 111 reviews, 5 bedrooms, 6 beds, 3 bathrooms
26 Sept – 1 Oct
Top guest favourite
Home in Marathon
World-Class Oceanfront Pool/Hottub Sunset Escape
5.0 out of 5 average rating, 38 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
29 Aug – 5 Sept
Top guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
4.94 out of 5 average rating, 17 reviews, 3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
Guest favourite
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug