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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, 24 reviews
Guest favourite
Apartment in Key West
Penthouse Waterfront Dock Pool Condo Near Duval St
4 bedrooms, 11 beds, 4 bathrooms
4–9 Oct
4.9 out of 5 average rating, 264 reviews
Guest favourite
Home in Key West
Gone Coastal 2
3 bedrooms, 5 beds, 2.5 bathrooms
10–15 Sept
4.93 out of 5 average rating, 126 reviews
Top guest favourite
Apartment in Key West
Coastline Comfort
2 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 9 reviews
Luxe
Home in Key West
The Dreamside House at Lunara Bay
8 bedrooms, 8 king beds, 8.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Key West
MERMAID COVE- Funky Getaway on Duval
4 bedrooms, 5 beds, 4 bathrooms
22–27 Sept
4.9 out of 5 average rating, 250 reviews
Luxe
Home in Key West
Spindrift House at Lunara Bay
4 bedrooms, 7 beds, 4 bathrooms
13–18 Sept
4.86 out of 5 average rating, 97 reviews
Guest favourite
Apartment in Key West
Waterfront Dock Pool Near Duval St Penthouse
4 bedrooms, 9 beds, 4 bathrooms
1–6 Sept
4.92 out of 5 average rating, 212 reviews
Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds, 3 bathrooms
9–14 Sept
5.0 out of 5 average rating, 41 reviews
Top guest favourite
Home in Key West
Casa Calypso 3bed3bath sleeps 8 beautiful decorate
3 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
5.0 out of 5 average rating, 39 reviews
Featured hotel
Room in Key West
One king bed accessible
1 bathroom
14–19 Sept
New place to stay
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, 12 reviews
Luxe
Home in Key West
The Windrose Estate at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
27 Sept – 2 Oct
4.9 out of 5 average rating, 30 reviews
Guest favourite
Flat in Key West
Luxury Designer Estate - Lunara Bay Collection
6 bedrooms, 8 beds, 6.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 13 reviews
Luxe
Home in Key West
The Starboard House at Solaire Lunara Bay
8 bedrooms, 11 beds, 8.5 bathrooms
7–12 Sept
4.9 out of 5 average rating, 10 reviews
Guest favourite
Home in Key West
Thompson Island USA !! Your Key West Retreat !!
9 bedrooms, 10 king beds, 6.5 bathrooms
6–11 Sept
4.79 out of 5 average rating, 105 reviews
Guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.81 out of 5 average rating, 26 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