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Search results; Over 1,000 homes in Key West

Superhost
Boat in Key West
Houseboat in Key West
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
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4.85 out of 5 average rating, 74 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, 18 reviews
Featured hotel
Hotel in Key West
Classic Double Queen City/Balcony
1 bedroom, 2 queen beds, 1 bathroom
13–18 Sept
4.81 out of 5 average rating, 73 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed, 1 bathroom
17–22 Sept
4.91 out of 5 average rating, 562 reviews
Hotel in Key West
*Near Smathers Beach | Pool + Dining & Bar
1 bedroom, 2 queen beds, 1 bathroom
13–18 Sept
4.71 out of 5 average rating, 35 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, 212 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds, 2 bathrooms
14–19 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, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 22 reviews
Luxe
Home in Key West
Altair House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
13–18 Sept
4.87 out of 5 average rating, 45 reviews
Top guest favourite
Casa particular in Key West
Amazing Canal front home in KW!
4 bedrooms, 5 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 41 reviews
Luxe
Home in Key West
Catchlight House at Lunara Bay
6 bedrooms, 9 beds, 6.5 bathrooms
11–16 Oct
4.98 out of 5 average rating, 42 reviews
Luxe
Home in Key West
Spindrift House at Lunara Bay
4 bedrooms, 7 beds, 4 bathrooms
13–18 Sept
4.85 out of 5 average rating, 99 reviews
Featured hotel
Hotel in Key West
Two bedrooms bi-level garden view suite
2 bedrooms, 1 bathroom
13–18 Sept
4.82 out of 5 average rating, 22 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
Guest favourite
Boat in Key West
Luxurious 40' Sailing Yacht!
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 25 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
Superhost
Home in Marathon
*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!
4 bedrooms, 5 beds, 3 bathrooms
30 Oct – 6 Nov
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Key West
William Skelton Home - Sleeps 16 just off Duval St
6 bedrooms, 10 beds, 4 bathrooms
25–30 Oct
4.98 out of 5 average rating, 60 reviews
Guest favourite
Boat in Key West
*August/September specials* off Grid Boat Key West
1 queen bed, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 95 reviews