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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
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
4–9 Oct
4.9 out of 5 average rating, 264 reviews
Guest favourite
Home in Key West
Gone Coastal 2
3 bedrooms, 5 beds
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
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
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
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
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
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
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
14–19 Sept
5.0 out of 5 average rating, 39 reviews
Featured hotel
Room in Key West
One king bed accessible
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
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
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
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
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
6–11 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
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
2–7 Sept
4.91 out of 5 average rating, 559 reviews