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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
7–12 Sept
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4.9 out of 5 average rating, 245 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, 30 reviews
Featured hotel
Room in Key West
Hearing Accessible Classic King City/Balcony
1 king bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 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, 14 reviews
Guest favourite
Boat in Key West
*August/September specials* off Grid Boat Key West
1 queen bed, 1 bathroom
5–10 Sept
4.96 out of 5 average rating, 95 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 561 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.96 out of 5 average rating, 210 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds, 2.5 bathrooms
8–13 Sept
4.88 out of 5 average rating, 177 reviews
Guest favourite
Houseboat in Key West
Tiki Suites~The Grand Tiki~Private Water Stay
1 bedroom, 1 bed, 1 bathroom
6–11 Sept
4.92 out of 5 average rating, 362 reviews
Guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
3 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
4.81 out of 5 average rating, 27 reviews
Superhost
Home in Marathon
NEW!The Hideaway~Pool~Pickleball~Putt-Putt~Kayaks!
3 bedrooms, 4 beds, 2 bathrooms
12–19 Sept
4.92 out of 5 average rating, 84 reviews
Guest favourite
Boat in Key West
“The Easy Way” Comfy, Practical, Convenient
1 bedroom, 1 king bed, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 24 reviews
Guest favourite
Boat in Key West
Waterfront Boat Stay + Resort Amenities
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 36 reviews
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
7–12 Sept
4.87 out of 5 average rating, 45 reviews
Featured hotel
Hotel in Key West
Two bedroom bi-level pool view suite
2 bedrooms, 1 bathroom
6–11 Sept
4.89 out of 5 average rating, 38 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 21 reviews
Featured hotel
Room in Key West
Havana king room
2 king beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Key West
Real World MTV House Key West - 18 to 22 guests
10 bedrooms, 13 beds, 5.5 bathrooms
5–10 Sept
4.87 out of 5 average rating, 126 reviews
Guest favourite
Boat in Key West
Sailboat Retreat | Resort Amenities
1 bedroom, 1 queen bed, 2 bathrooms
8–13 Sept
4.93 out of 5 average rating, 55 reviews