Vacation Rentals in Key West

$150 CAD
Per Night

Beach house in the Sky B317
Vacation Rental in Key West, United States
2 Bedrooms · 4 Guests · #353717

$338 CAD
Per Night

Ocean Extravaganza Premiere Penthouse C438
Vacation Rental in Key West, United States
2 Bedrooms · 4 Guests · #351079

$125 CAD
Per Night

Vibe in Paradise Key West B217
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #346279

$270 CAD
Per Night

Botanical Island Delight C120
Vacation Rental in Key West, United States
2 Bedrooms · 4 Guests · #346278

$270 CAD
Per Night

Coconut Palms Key West A213
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #352505

$161 CAD
Per Night

Awaken to the Morning Reflections C437
Vacation Rental in Key West, United States
2 Bedrooms · 4 Guests · #354006

$270 CAD
Per Night

Turtle Cay Island Delight C327
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #352015

$315 CAD
Per Night

Latitude Penthouse Key West B417
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #353637

$139 CAD
Per Night

Luxurious Island Gem A109
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #351972

$315 CAD
Per Night

Atlantic Oasis Penthouse on the Ocean C420
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #346282

$315 CAD
Per Night

Mojitos Island Oasis C238
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #346277

$200 CAD
Per Night

Truman Annex Irish Condo Innisfree
Vacation Rental in Key West, United States
2 Bedrooms · 4 Guests · #346287

$315 CAD
Per Night

Bimini Key West Penthouse C424
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #346284

$270 CAD
Per Night

Tropical Paradise on the Atlantic Ocean A113
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #352387

$270 CAD
Per Night

Nautical Adventures in Paradise C126
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #346288

$89 CAD
Per Night

William's Loft: 2 BR / 1 BA cottage in Key West, Sleeps 3
Vacation Rental in Key West, United States
2 Bedrooms · 3 Guests · #349325

$143 CAD
Per Night

Anglers Escape Crystal Waters C429
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #353787

$59 CAD
Per Night

Bahama Treehouse Studio
Vacation Rental in Key West, United States
1 Bedroom · 2 Guests · #353703

$315 CAD
Per Night

Hemingways Atlantic Retreat C339
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #351906

$107 CAD
Per Night

Shrimp Party: 2 BR / 2 BA townhouse in Key West, Sleeps 4
Vacation Rental in Key West, United States
2 Bedrooms · 4 Guests · #349314

$270 CAD
Per Night

Paradise Found Cayo Hueso A111
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #346286

$107 CAD
Per Night

TROPICAL CASITA PRIVATE HOME WITH LARGE POOL A SECLUDED HIDEAWAY IN OLD TOWN KEY WEST
Vacation Rental in Key West, United States
1 Bedroom · 2 Guests · #349286

$270 CAD
Per Night

Tropical Orchid Oasis on the Atlantic B117
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #351901

$270 CAD
Per Night

Leeward Isle Retreat A105
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #352792

$134 CAD
Per Night

Casa Coastal East C231
Vacation Rental in Key West, United States
2 Bedrooms · 6 Guests · #353917

View Results on Map
Key West Vacation Rentals, Cottages & More!

Located at the southernmost tip of the Florida Keys (and continental U.S.A), Key West has vacation rentals to suit every style and budget.

While the rest of the Florida Keys are popular with diving and fishing enthusiasts, Key West is bigger with the laid-back city set. The island is filled with nineteenth century architecture, art galleries, museums, and heritage homes, including the Ernest Hemingway Home & Museum and the Harry S. Truman Little White House. Duval Street, Key West’s main thoroughfare, is home to world-class restaurants, sidewalk cafés, open-air bars, and legendary pubs, such as the famed Sloppy Joe’s and the original Jimmy Buffett’s Margaritaville. The island has long attracted artists, renegades, and free spirits, which has much imbued colour to its streets. 

Key Largo offers a vast array of natural and cultural attractions, as well as a variety of facilities and rental accommodation options, and is situated 250 kilometres southwest from Miami, and 150 miles from Havana.

+ More