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Search results; Over 1,000 homes in Key West

Guest favourite
Apartment in Key West
Orchid Bay Condo + Pool • Old Town • Walk to Duval
1 bedroom, 2 beds, 1 private bathroom
31 Oct – 5 Nov
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4.92 out of 5 average rating, 152 reviews
Featured hotel
Hotel in Key West
Classic Double Queen City/Balcony
1 bedroom, 2 queen beds
13–18 Sept
4.81 out of 5 average rating, 73 reviews
Featured hotel
Rooms in Key West
Two bedrooms bi-level garden view suite
2 bedrooms
13–18 Sept
4.82 out of 5 average rating, 22 reviews
Featured hotel
Room in Key West
Havana king accessible
1 king bed
13–18 Sept
Featured hotel
Hotel in Key West
King city single room
1 bedroom, 1 king bed
13–18 Sept
5.0 out of 5 average rating, 25 reviews
Featured hotel
Hotel in Key West
Havana king room
1 bedroom, 2 king beds
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Featured hotel
Room in Key West
Queen Room
1 queen bed
15–20 Sept
5.0 out of 5 average rating, 16 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
Featured hotel
Hotel in Key West
Luxury second floor balcony suite
1 bedroom, 1 king bed
13–18 Sept
4.94 out of 5 average rating, 17 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
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds
13–18 Sept
4.71 out of 5 average rating, 35 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
17–22 Sept
4.91 out of 5 average rating, 561 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds
13–18 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Key West
Casa Cristol - Truman Annex
3 bedrooms, 3 beds
13–18 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds
24–29 Oct
4.96 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
16–21 Sept
5.0 out of 5 average rating, 41 reviews
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds
13–18 Sept
4.87 out of 5 average rating, 45 reviews
Guest favourite
Boat in Key West
Amazing 4 Bdrm, 4 Bath Catamaran- Sleeps up to 8
4 bedrooms, 4 beds
27 Sept – 2 Oct
4.89 out of 5 average rating, 37 reviews
Luxe
Home in Key West
Catchlight House at Lunara Bay
6 bedrooms, 9 beds
11–16 Oct
4.98 out of 5 average rating, 42 reviews