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Search results; Over 1,000 homes in Key West

Top guest favourite
Flat in Key West
Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
2 bedrooms, 1 bed, 1 private bathroom
12–17 Sept
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4.98 out of 5 average rating, 565 reviews
Featured hotel
Room in Key West
Hearing Accessible Classic King City/Balcony
1 king bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 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, 21 reviews
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds
12–17 Sept
4.74 out of 5 average rating, 34 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
Guest favourite
Apartment in Key West
Waterfront Dock Pool Near Duval St Penthouse
4 bedrooms, 9 beds
4–9 Oct
4.92 out of 5 average rating, 217 reviews
Superhost
Home in Key West
Poolside Paradise
3 bedrooms, 6 beds
11–16 Oct
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
Guest favourite
Boat in Key West
Waterfront & Heated Pool - Away Awai Floating Vill
2 bedrooms, 2 queen beds
12–17 Sept
4.93 out of 5 average rating, 87 reviews
Guest favourite
Apartment in Key West
EYW Getaway
2 bedrooms, 3 beds
19–24 Sept
4.99 out of 5 average rating, 86 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
Guest favourite
Home in Key West
Gone Coastal 2
3 bedrooms, 5 beds
25–30 Sept
4.93 out of 5 average rating, 129 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
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, 17 reviews
Top guest favourite
Apartment in Key West
Waterfront Condo | Pool, Dock, Parking, Sleeps 8
2 bedrooms, 4 beds
8–13 Oct
4.87 out of 5 average rating, 306 reviews
Guest favourite
Tiny home in Key West
Downtown Studio half block from Duval w parking
1 bed
26 Sept – 1 Oct
4.86 out of 5 average rating, 478 reviews
Top guest favourite
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds
3–10 Oct
5.0 out of 5 average rating, 5 reviews
Guest favourite
Boat in Key West
“The Easy Way” Comfy, Practical, Convenient
1 bedroom, 1 king bed
12–17 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Houseboat in Key West
Strictly Pleasure | Unique Yacht Stay in the Keys
2 bedrooms, 2 beds
12–17 Sept
5.0 out of 5 average rating, 22 reviews