Key West Vacation Rentals & House Rentals - 65 Rentals Available
65 Vacation rentals
2 bedroom Condo Presented Key West Style
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Nearest beach 2 mi
- Swimming pool
- Child friendly
$210
from $210 / night
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
Key West Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 2 nights min
- Swimming pool
- Child friendly
- Air conditioning
$209
from $209 / night
Key West Condo 2 br, 2ba - ocean veiw from balcony
Key West Condo
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$250
from $250 / night
Penthouse Condo in Key West Florida
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 1 night min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$295
from $295 / night
Harbor Walk Hideaways
Key West B and B
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Beach/lakeside relaxation
- Nearest beach 0.2 mi
- Swimming pool
$730
from $730 / night
Best Old Town Location in Key West
Key West Townhouse
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Swimming pool
- Ask about children
- Car not necessary
$200
from $200 / night
Beautiful, Oversize 2BR/King Beds w/ Large Outdoor Spaces, Location! Truman Annx
Key West Condo
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Nearest beach 0.5 mi
- Swimming pool
- Child friendly
$228
from $228 / night
Ocean Front View Every Room*90' Scenic Balcony WIFI IN KEY WEST NOT ISLANDS AWAY
Key West Condo
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- 30 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$209
from $209 / night
Beautiful, End-Unit 2BR King/twins, Large, Private Deck. Location! Truman Annex
Key West Condo
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Nearest beach 0.5 mi
- Swimming pool
- Child friendly
$186
from $186 / night
737 The Place, a Monthly Rental Old Town Key West
Key West Apartment
- 1 bedroom 1
- 1 bathroom
- Sleeps 2 2
- 30 nights min
- Beach/lakeside relaxation
- Nearest beach 0.5 mi
- Ask about children
$60
from $60 / night
Conch Wind
Key West House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$275
from $275 / night
Leeward Isle Key West Retreat
Key West House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$275
from $275 / night
Tranquility
Key West Cottage
- 1 bedroom 1
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Ask about pets
$215
from $215 / night
Amelia Home
Key West House
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$345
from $345 / night
Parrot Perch
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$235
from $235 / night
Island Wind
Key West House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$275
from $275 / night
Beach House Condo
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$250
from $250 / night
The Dolphin House
Key West House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$665
from $665 / night
Alluring Porches
Key West House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$290
from $290 / night
Easy Livin'
Key West House
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$583
from $583 / night
The Hemingway
Key West House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$230
from $230 / night
Here Tomorrow
Key West House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
$253
from $253 / night
Artist Garden
Key West House
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$315
from $315 / night
President's Walk
Key West House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Pet friendly
$245
from $245 / night
Duval Penthouse
Key West House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 7 7
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$595
from $595 / night
Truman's Hideaway
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$315
from $315 / night
A Barefoot Retreat
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$215
from $215 / night
Tropical Dreaming
Key West House
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$345
from $345 / night
Atlantic Paradise
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Ask about pets
$230
from $230 / night
Sundown Refuge
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$330
from $330 / night
Conch Condo
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$235
from $235 / night
Shipyard Treasure
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$215
from $215 / night
Southard Getaway
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
$230
from $230 / night
Lavender Jungle
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Ask about pets
$205
from $205 / night
Duval Breeze
Key West House
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Ask about pets
$240
from $240 / night
About Key West
A Short History of Key West
At the very end of the Florida Keys, this four-square-mile island was first settled by Spanish explorers led by Ponce de León. The remote location was sparsely populated until it was claimed by the United States in the early 19th century. By the turn of the 20th century, Key West was actually the largest and most moneyed city in Florida, thanks to its quick development, naval base, and cigar industry. The locale began to develop its reputation as a tourist hotspot around that time, and this southernmost U.S. city still holds that identity today.
What Key West Does Best
This small island is packed with attractions and activities. Surrounded by the Gulf of Mexico, Key West offers visitors ample natural beauty and great swimming beaches. History buffs love the island’s maritime history and legends of its famous residents, while partygoers can’t get enough of Duval Street, the center of Key West’s nightlife scene.
Natural Beauty
Key West isn’t known for its beaches, but Fort Zachary Taylor Historic State Park is a great place to swim, snorkel, and catch the sunset. Explore the waters around Key West by sailboat, kayak, or sunset cruise to get a closer look at the sparkling gulf. For a unique adventure, head 70 miles offshore to Dry Tortugas National Park. Explore Fort Jefferson, the coral reefs, and the island’s impressive variety of wildlife and tropical plants.Historical Markers
To get a quick look at everything Key West has to offer, hop on the Conch Tour Train. You’ll get an earful of the area’s past, along with a little local trivia. When you’re ready to dig in, make the Ernest Hemingway Home & Museum your first stop. Here you can learn more about the famous writer’s life and see where he penned some of his best selling novels.Don't miss a tour of the Harry S. Truman Little White House, a command center during World War I and II as well as the winter home of President Harry S. Truman. Today the house is both a museum and a political retreat, and it’s well worth a visit.
Vibrant Nightlife
No trip to Key West is complete without a night out on the town, and options range from family-friendly to wildly theatrical. Take the family to Mallory Square, where you’ll find local performers, plenty of fried food, and gorgeous sunset views. For some grownup fun, take in a performance at Key West’s Fringe Theater, the Red Barn Theatre, or the Waterfront Playhouse. Finish the night off with a drink at the Green Parrot, Key West’s oldest bar, or Sloppy Joe’s, one of Hemingway’s favorite hangouts.Whether you prefer culture or the outdoors, Key West has plenty to offer in a relaxed, welcoming atmosphere. One night here isn’t enough, so book a vacation home and stay awhile on this island destination.
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