Key West Vacation Rentals & House Rentals - 88 Rentals Available
88 Vacation rentals
Certificate of Excellence
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
Key West Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 51 minutes
Travelers’ Choice award
$240.00
from $240.00 / night
2 bedroom Condo Presented Key West Style
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Nearest beach 2 mi
- Swimming pool
- Child friendly
Responds fast! Avg. 43 minutes
$10.00
from $10.00 / night
6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location
Key West Villa
- 6 bedrooms 6
- 7 bathrooms
- sleeps 16 16
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$2,004.00
from $2,004.00 / 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
$900.00
from $900.00 / night
Duval Penthouse - private pool/parking with roof deck - A++ Location
Key West Penthouse
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Nearest beach 1 mi
- Child friendly
- Car not necessary
$796.00
from $796.00 / night
Bahama House - A++ Location with private pool/parking - walk to everything!
Key West House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$773.00
from $773.00 / 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
$115.00
from $115.00 / night
Southard Square Hideaway
Key West Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$223.00
from $223.00 / night
Southard Getaway
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$195.00
from $195.00 / night
Sunny View
Key West House
- 1 bedroom 1
- 2 bathrooms
- sleeps 2 2
- min stay varies
- Child friendly
- Air conditioning
$191.00
from $191.00 / night
Bayview Harbor
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$160.00
from $160.00 / night
Artist Garden
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$285.00
from $285.00 / night
President's Walk
Key West House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$195.00
from $195.00 / night
William's Loft
Key West Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 3 3
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$193.00
from $193.00 / night
Lighthouse Villa
Key West House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$445.00
from $445.00 / night
Key West Found
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$250.00
from $250.00 / night
Newton's Nest
Key West Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$167.00
from $167.00 / night
First Breath
Key West House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$100.00
from $100.00 / night
Emma's Escape
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$185.00
from $185.00 / night
Coconut Cottage
Key West House
- 1 bedroom 1
- 2 bathrooms
- sleeps 2 2
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$209.00
from $209.00 / night
Duval Breeze
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$241.00
from $241.00 / night
A Barefoot Retreat
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$180.00
from $180.00 / night
Boat House
Key West House
- 1 bedroom 1
- 2 bathrooms
- sleeps 2 2
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$216.00
from $216.00 / night
A Place In Paradise
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$225.00
from $225.00 / night
Linger Longer
Key West House
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$180.00
from $180.00 / night
Conch Republic Retreat
Key West Cottage
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$238.00
from $238.00 / night
Lazy Gecko
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Child friendly
- Air conditioning
$232.00
from $232.00 / night
Tranquility
Key West Cottage
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$175.00
from $175.00 / night
Sundown Refuge
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$264.00
from $264.00 / night
Flagler Station
Key West House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$278.00
from $278.00 / night
Amelia Home
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$325.00
from $325.00 / night
tropical Casita
Key West House
- 1 bedroom 1
- 2 bathrooms
- sleeps 2 2
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$241.00
from $241.00 / night
Shrimp Party
Key West Townhouse
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$248.00
from $248.00 / night
Key Lime Pie
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$219.00
from $219.00 / night
Perfect Pineapple
Key West House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$241.00
from $241.00 / 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.
What is Travelers’ Choice award?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.