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Search results; Over 1,000 homes in Key West

Guest favourite
Apartment in Key West
Waterfront Dock Pool Key West Near Duval
2 bedrooms, 4 beds, 2 private bathrooms
3–8 Sept
,
4.83 out of 5 average rating, 231 reviews
Top guest favourite
Apartment in Key West
September special 119/nt-walk to Duval, Mallory
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 59 reviews
Featured hotel
Room in Key West
One queen bed
1 bathroom
6–11 Sept
4.85 out of 5 average rating, 20 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
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
Home in Key West
Old Town Key West Escape - The “Eyebrow Saltbox”
3 bedrooms, 3 beds, 2 bathrooms
7–14 Sept
4.88 out of 5 average rating, 16 reviews
Featured hotel
Room in Key West
Classic Double Queen City/Balcony
2 queen beds, 1 bathroom
7–12 Sept
4.81 out of 5 average rating, 64 reviews
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
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
Top guest favourite
Apartment in Key West
Coastline Comfort
2 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Marathon
NEW! Private Pool, 50’ Dock, Kayaks, Waterfront
3 bedrooms, 2.5 bathrooms
23–30 Sept
4.97 out of 5 average rating, 39 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
4.96 out of 5 average rating, 208 reviews
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
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
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
Guest favourite
Home in Key West
Paradise found
3 bedrooms, 4 beds, 3 bathrooms
7–12 Sept
4.94 out of 5 average rating, 156 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
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
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
24–31 Oct
5.0 out of 5 average rating, 89 reviews