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Search results; Over 1,000 homes in Key West

Guest favourite
Apartment in Key West
Condo de Paradise/Salt Water Pool/Boat Dock
2 bedrooms, 3 beds, 2 private bathrooms
5–12 Aug
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4.96 out of 5 average rating, 45 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
5.0 out of 5 average rating, 8 reviews, 2 queen beds, 1 bathroom
16–21 Aug
Featured hotel
Room in Key West
Ocean view one king bed accessible
New place to stay, 1 bathroom
14–19 Aug
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
4.91 out of 5 average rating, 99 reviews, 3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
4.91 out of 5 average rating, 554 reviews, 1 bedroom, 1 bed, 1 bathroom
18–23 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
Luxury Boating Paradise+Pool+Sailing Kayaks
5.0 out of 5 average rating, 85 reviews, 4 bedrooms, 8 beds, 3 bathrooms
15–22 Aug
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
Superhost
Apartment in Key West
Free Boat Slip | Waterfront Condo | Key West Pool
New place to stay, 2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
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
7–12 Aug
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
4.97 out of 5 average rating, 203 reviews, 2 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 4 beds, 3.5 bathrooms
29 Aug – 5 Sept
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 1 bathroom
15–20 Aug
Guest favourite
Home in Key West
Waterfront Home in Key Cove Landings
5.0 out of 5 average rating, 24 reviews, 4 bedrooms, 6 beds, 3 bathrooms
9–14 Aug
Guest favourite
Home in Key West
Gone Coastal 2
4.93 out of 5 average rating, 121 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
18–23 Aug
Superhost
Home in Key West
Poolside Paradise
New place to stay, 3 bedrooms, 6 beds, 3 bathrooms
18–23 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
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4.84 out of 5 average rating, 25 reviews, 4 bedrooms, 5 beds, 4.5 bathrooms
1–6 Aug
Guest favourite
Home in Marathon
Beach House in Marathon with Amazing Backyard!
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 4 beds, 2 bathrooms
9–16 Aug