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Search results; Over 1,000 homes in Key West

Superhost
Home in Marathon
Mar de Cielo - Waterfront - Heated Pool - Dock
4 bedrooms, 9 beds, 3 bathrooms
1–8 Sept
New place to stay
Superhost
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds, 3.5 bathrooms
5–12 Sept
5.0 out of 5 average rating, 4 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
13–18 Sept
4.82 out of 5 average rating, 22 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
2–7 Sept
4.91 out of 5 average rating, 558 reviews
Superhost
Home in Marathon
*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!
4 bedrooms, 5 beds, 3 bathrooms
26 Sept – 3 Oct
New place to stay
Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds, 2 bathrooms
7–12 Sept
New place to stay
Superhost
Home in Key West
Pilar's Secret - walking distance to everything!
3 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
4.92 out of 5 average rating, 88 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds, 4 bathrooms
5–10 Oct
4.91 out of 5 average rating, 102 reviews
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bathroom
11–16 Sept
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 11 reviews
Luxe
Home in Key West
The Seagate Estate at Lunara Bay
4 bedrooms, 5 beds, 4.5 bathrooms
20–25 Sept
4.81 out of 5 average rating, 63 reviews
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds, 4.5 bathrooms
7–12 Sept
4.84 out of 5 average rating, 31 reviews
Luxe
Home in Key West
Catchlight House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
11–16 Oct
4.98 out of 5 average rating, 40 reviews
Superhost
Home in Key West
Mango Cottage, a charming Key West home ready for
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.91 out of 5 average rating, 130 reviews
Superhost
Home in Marathon
*NEW* Reel Escape~Dock!~Lift!~Pet Friendly~Grill!
3 bedrooms, 3 beds, 2 bathrooms
10–17 Sept
New place to stay
Superhost
Boat in Key West
Waterfront & Heated Pool - Break Awai Floating Vil
2 bedrooms, 2 queen beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Houseboat in Marathon
b watervibe
1 bedroom, 1 small double bed, 1 bathroom
27 Sept – 2 Oct
4.92 out of 5 average rating, 93 reviews
Top guest favourite
Apartment in Key West
Waterfront Condo Dock Pool Near Duval St
2 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.89 out of 5 average rating, 150 reviews