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Search results; Over 1,000 homes in Key West

Top guest favourite
Home in Key West
Gorgeous Romantic Private Villa, Steps from Duval!
1 bedroom, 2 beds, 1.5 private bathrooms
7–12 Sept
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4.96 out of 5 average rating, 110 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
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
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
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
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
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
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
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
Superhost
Home in Marathon
*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!
4 bedrooms, 5 beds, 3 bathrooms
30 Oct – 6 Nov
New place to stay
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
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
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
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
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
6 bedrooms, 6 beds, 6.5 bathrooms
12–17 Oct
5.0 out of 5 average rating, 28 reviews
Guest favourite
Home in Marathon
Marlin House | Waterfront Pool Home Near Marina
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 6 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
Top guest favourite
Home in Key West
Poolside Paradise/3bed, 2.5 bath/Pvt. Pool and Spa
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 31 reviews