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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, 3.5 bathrooms
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, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 359 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
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, 559 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
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
Catchlight House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
11–16 Oct
4.98 out of 5 average rating, 40 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
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
Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds, 2 bathrooms
7–12 Sept
New place to stay
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
4–9 Oct
4.86 out of 5 average rating, 44 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, 32 reviews
Featured hotel
Room in Key West
One queen bed
1 bathroom
6–11 Sept
4.86 out of 5 average rating, 21 reviews
Top guest favourite
Home in Marathon
Waterfront 6BR Luxury Retreat w/ Pool & Dock
6 bedrooms, 10 beds, 5 bathrooms
19–26 Sept
5.0 out of 5 average rating, 31 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
13–18 Sept
4.83 out of 5 average rating, 23 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
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
Home in Key West
William Skelton Home - Sleeps 16 just off Duval St
6 bedrooms, 10 beds, 4 bathrooms
24–29 Sept
4.98 out of 5 average rating, 58 reviews