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Search results; Over 1,000 homes in Key West

Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 private bathroom
17–22 Sept
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4.91 out of 5 average rating, 562 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds
14–19 Sept
4.71 out of 5 average rating, 35 reviews
Hotel in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 bedroom, 1 king bed
14–19 Sept
4.74 out of 5 average rating, 23 reviews
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds
11–16 Oct
Top guest favourite
Apartment in Key West
Waterfront Condo Dock Pool Near Duval St
2 bedrooms, 4 beds
21–26 Sept
4.9 out of 5 average rating, 155 reviews
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, 18 reviews
Guest favourite
Room in Key West
Mallory House Room #2
1 queen bed
20–25 Sept
4.91 out of 5 average rating, 443 reviews
Guest favourite
Boat in Key West
3BR In Resort Village, Pools, Free Kayak & Shuttle
3 bedrooms, 3 beds
2–7 Oct
4.81 out of 5 average rating, 27 reviews
Guest favourite
Home in Key West
Waterlane House at Lunara Bay
4 bedrooms, 7 beds
27 Sept – 2 Oct
4.85 out of 5 average rating, 112 reviews
Featured hotel
Hotel in Key West
Classic Double Queen City/Balcony
1 bedroom, 2 queen beds
14–19 Sept
4.81 out of 5 average rating, 74 reviews
Top guest favourite
Boat in Key West
All Inclusive! Snorkel • Sail • Sun & Fun
3 bedrooms, 3 queen beds
17–22 Sept
4.88 out of 5 average rating, 177 reviews
Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds
25–30 Sept
5.0 out of 5 average rating, 3 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
Top guest favourite
Hotel room in Key West
The Sanchez House Room #2
1 bedroom, 1 queen bed
3–8 Oct
4.85 out of 5 average rating, 711 reviews
Guest favourite
Home in Key West
Thompson Island USA !! Your Key West Retreat !!
9 bedrooms, 10 king beds
14–19 Sept
4.79 out of 5 average rating, 105 reviews
Top guest favourite
Home in Key West
Pilar House
3 bedrooms, 3 beds
13–18 Dec
4.96 out of 5 average rating, 47 reviews
Guest favourite
Home in Key West
Gone Coastal 2
3 bedrooms, 5 beds
25–30 Sept
4.93 out of 5 average rating, 130 reviews
Guest favourite
Flat in Key West
Duval Balcony Spanky's Retreat
1 bedroom, 2 beds
26 Sept – 1 Oct
4.91 out of 5 average rating, 899 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds
21–26 Sept
5.0 out of 5 average rating, 22 reviews