Key West Vacation Rentals & House Rentals - 106 Rentals Available
106 Vacation rentals
SPECIAL DISCOUNT! 45' Sailboat & Other Yachts
Key West Yacht
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$250.00
from $250.00 / night
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
Certificate of Excellence
$209.00
from $209.00 / night
Key West's only Real Beach House
Key West Guest house
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$393.00
from $393.00 / night
Private beach estate. Gated, tropical peace and quiet. Dock.
Key West House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$465.00
from $465.00 / 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
$215.00
from $215.00 / night
Key's only real beach home. Dock and pool.
Key West House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$343.00
from $343.00 / night
Key's only real beach home.Gated, private, dock,pool
Key West House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$536.00
from $536.00 / night
Harbor Walk Hideaways
Key West B and B
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0.2 mi
- Swimming pool
$801.00
from $801.00 / 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
$101.00
from $101.00 / night
Private beach estate.Dock and pool.
Key West House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 30 nights min
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$284.00
from $284.00 / night
Private beach estate,gated,dock,and pool.
Key West House
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 10 10
- 28 nights min
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$743.00
from $743.00 / night
The Key's only real beach house Dock and pool
Key West House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$394.00
from $394.00 / night
Best Old Town Location in Key West
Key West Townhouse
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Car not necessary
$258.00
from $258.00 / night
Flagler Station
Key West House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$268.00
from $268.00 / 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
Sunshine Key West
Key West House
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$286.00
from $286.00 / night
First Breath
Key West House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$268.00
from $268.00 / night
Emma's Secret
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$166.00
from $166.00 / night
Hidden Treasure
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$170.00
from $170.00 / night
Sunny View
Key West House
- 1 bedroom 1
- 2 bathrooms
- Sleeps 2 2
- Min stay varies
- Child friendly
- Air conditioning
$179.00
from $179.00 / night
Alluring Porches
Key West House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$275.00
from $275.00 / night
Coral Villa
Key West House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$245.00
from $245.00 / night
Bogey's Retreat
Key West House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$148.00
from $148.00 / night
A Little Slice Of Paradise
Key West House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$157.00
from $157.00 / night
Siesta Bay
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$171.00
from $171.00 / night
Beach House Condo
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$210.00
from $210.00 / night
Green Orchid
Key West House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Child friendly
- Air conditioning
- Pet friendly
$197.00
from $197.00 / night
Atlantic Paradise
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$201.00
from $201.00 / night
Here Tomorrow
Key West House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$275.00
from $275.00 / night
Perfect Pineapple
Key West House
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$221.00
from $221.00 / night
Key West Ginger Whole House
Key West Cottage
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Child friendly
- Air conditioning
- Pet friendly
$201.00
from $201.00 / night
Key West Charming
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$176.00
from $176.00 / night
Duval On The Square
Key West House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$234.00
from $234.00 / night
Duval Sea Turtle
Key West House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$210.00
from $210.00 / night
Breezy Bungalow
Key West House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$225.00
from $225.00 / night
Captains Wheel
Key West House
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$210.00
from $210.00 / night
The Dolphin House
Key West House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$600.00
from $600.00 / night
Bowe Conch House
Key West House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Child friendly
- Air conditioning
$184.00
from $184.00 / 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 Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.