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Search results; Over 1,000 homes in Key West

Apartment in Key West
One Bedroom Suite | Beachside Resort
1 bedroom, 2 beds, 1.5 private bathrooms
8–13 Sept
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4.8 out of 5 average rating, 113 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, 15 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
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds, 1 bathroom
13–18 Sept
4.84 out of 5 average rating, 32 reviews
Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds, 3 bathrooms
11–16 Sept
5.0 out of 5 average rating, 41 reviews
Guest favourite
Houseboat in Key West
Tiki Suites~The Grand Tiki~Private Water Stay
1 bedroom, 1 bed, 1 bathroom
8–13 Sept
4.92 out of 5 average rating, 362 reviews
Featured hotel
Hotel in Key West
Two bedroom bi-level pool view suite
2 bedrooms, 1 bathroom
8–13 Sept
4.89 out of 5 average rating, 38 reviews
Featured hotel
Room in Key West
Accessible Classic Double Queen City/Balcony
2 queen beds, 1 bathroom
20–25 Sept
4.71 out of 5 average rating, 7 reviews
Guest favourite
Boat in Key West
*August/September specials* off Grid Boat Key West
1 queen bed, 1 bathroom
8–13 Sept
4.96 out of 5 average rating, 95 reviews
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
4–9 Oct
4.87 out of 5 average rating, 45 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, 211 reviews
Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 bathroom
10–15 Sept
4.9 out of 5 average rating, 245 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds, 2.5 bathrooms
9–14 Sept
4.88 out of 5 average rating, 177 reviews
Top guest favourite
Apartment in Key West
Coastline Comfort
2 bedrooms, 4 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Key West
Poolside Paradise/3Brs, 2.5 bath/Pvt. Pool/Spa
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 36 reviews
Guest favourite
Home in Key West
Real World MTV House Key West - 18 to 22 guests
10 bedrooms, 13 beds, 5.5 bathrooms
16–21 Sept
4.87 out of 5 average rating, 126 reviews
Guest favourite
Boat in Key West
Amazing 4 Bdrm, 4 Bath Catamaran- Sleeps up to 8
4 bedrooms, 4 beds, 4 bathrooms
8–13 Sept
4.89 out of 5 average rating, 37 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
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