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Search results; Over 1,000 homes in Key West

Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 private bathroom
6–11 Sept
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4.9 out of 5 average rating, 245 reviews
Superhost
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds
5–12 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Houseboat in Key West
Tiki Suites~The Grand Tiki~Private Water Stay
1 bedroom, 1 bed
7–12 Sept
4.92 out of 5 average rating, 359 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
2–7 Sept
4.91 out of 5 average rating, 558 reviews
Superhost
Home in Key West
Pilar's Secret - walking distance to everything!
3 bedrooms, 5 beds
14–19 Sept
4.92 out of 5 average rating, 88 reviews
Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds
7–12 Sept
New place to stay
Luxe
Home in Key West
The Seagate Estate at Lunara Bay
4 bedrooms, 5 beds
20–25 Sept
4.81 out of 5 average rating, 63 reviews
Featured hotel
Room in Key West
One queen bed
6–11 Sept
4.85 out of 5 average rating, 20 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds
13–18 Sept
4.82 out of 5 average rating, 22 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds
24–31 Oct
5.0 out of 5 average rating, 89 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds
5–10 Oct
4.91 out of 5 average rating, 102 reviews
Luxe
Home in Key West
Catchlight House at Lunara Bay
6 bedrooms, 9 beds
11–16 Oct
4.98 out of 5 average rating, 40 reviews
Superhost
Home in Marathon
*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!
4 bedrooms, 5 beds
30 Oct – 6 Nov
New place to stay
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds
4–9 Oct
4.86 out of 5 average rating, 44 reviews
Top guest favourite
Apartment in Key West
September special 119/nt-walk to Duval, Mallory
2 bedrooms, 2 beds
7–12 Sept
4.92 out of 5 average rating, 59 reviews
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
6 bedrooms, 6 beds
12–17 Oct
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds
20–25 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds
7–12 Sept
4.84 out of 5 average rating, 31 reviews
Top guest favourite
Home in Key West
Lennon's Lodge, Luxury Accommodations for up to 6!
2 bedrooms, 3 beds
19–24 Sept
4.96 out of 5 average rating, 255 reviews