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Search results; Over 1,000 homes in Key West

Houseboat in Key West
Key West Luxury Houseboat at Yacht Club Resort
2 bedrooms, 3 beds, 2.5 private bathrooms
6–11 Jul
,
4.81 out of 5 average rating, 295 reviews
Superhost
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
13–18 Jul
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
Luxe
Home in Marathon
The Pearl at SeaGlass Cove Waterfront Luxury Home!
5 bedrooms, 5 beds, 4.5 bathrooms
9–16 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
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
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
Flat in Key West
Beautiful Corner Condo Overlooking Pool
2 bedrooms, 4 beds, 2 bathrooms
8–13 Aug
Luxe
Home in Key West
The Greenmoor House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Marathon
Sombrero Sunset-Marathon 7BR 6BA Waterfront Pool
7 bedrooms, 8 beds, 6 bathrooms
29 Aug – 5 Sept
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Home in Marathon
Angler’s Terrace Conde Nast Traveler’s Best Airbnb
4 bedrooms, 6 beds, 3 bathrooms
28 Nov – 5 Dec
4.97 out of 5 average rating, 145 reviews
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, 37 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
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
22–27 Aug
4.91 out of 5 average rating, 97 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
Top guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 15 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
2–7 Aug
4.54 out of 5 average rating, 24 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
15–22 Aug
5.0 out of 5 average rating, 84 reviews
Top guest favourite
Home in Marathon
Oceanfront 5BR+Bonus Sunrise Pool Spa •Dock•Beach
5 bedrooms, 10 beds, 6 bathrooms
15–22 Aug
5.0 out of 5 average rating, 15 reviews