Search 105,200+ Vacation Rentals

Key West Vacation Rentals & House Rentals - 65 Rentals Available

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

65 Vacation rentals

(123)

1 / 28

Key West Apartment

  • 2
  • 6
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
“we can"t say enough about the condo or Pam. She takes good care of her rental. Always clean and comfortable.The balcony overlooks the pool area which is well maintained. Pam is always available to answer any questions you might have. We stay the...”
- Review left on 12/03/2016

$210

Excellent (123 reviews)

Book

from $210 / night

(53)

1 / 36

Key West Condo

  • 2
  • 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We enjoyed our stay at the Sunrise Suite. The place was bright with sunshine. It was clean, comfortable, nice sitting balcony and close to Duval Street. It had everything you would need for your stay. You could walk thru the complex and cross the...”
- Review left on 03/06/2017

$209

Excellent (53 reviews)

Book

from $209 / night

(7)

1 / 12

Key West Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$250

Very Good (7 reviews)

Book

from $250 / night

(3)

1 / 6

Key West Apartment

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$295

Very Good (3 reviews)

Book

from $295 / night

(20)

1 / 22

Key West B and B

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$730

Excellent (20 reviews)

Inquire

from $730 / night

(17)

1 / 17

Key West Townhouse

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary
“This unit was great! The location is fantastic! The condo is spacious, clean and everything we were hoping for. I like that the bedrooms are upstairs which offers more privacy...”
- Review left on 01/12/2017

$200

Excellent (17 reviews)

Inquire

from $200 / night

(5)

1 / 15

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
“We stayed for a week and had a wonderful holiday. The booking and communication with the owner was good and the accommodation is exactly as described. It is a lovely clean well equipped apartment in a central location. Easy walk to all of the...”
- Review left on 07/13/2016

$228

Excellent (5 reviews)

Book

from $228 / night

(2)

1 / 18

Key West Condo

  • 3
  • 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$209

Excellent (2 reviews)

Book

from $209 / night

(5)

1 / 14

Key West Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
“We (2 retired couples) enjoyed our stay at Rooster Retreat. What you see in the pictures is true to what you get, but I will add that the "twins to king conversion" is probably the best I have ever experienced. It just did not "feel" like twins --...”
- Review left on 03/12/2017

$186

Very Good (5 reviews)

Book

from $186 / night

(1)

1 / 15

Key West Apartment

  • 1
  • 2
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Ask about children

$60

Excellent (1 reviews)

Book

from $60 / night

(32)

1 / 24

Key West Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$205

Very Good (32 reviews)

Inquire

from $205 / night

(36)

1 / 23

Key West House

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$275

Very Good (36 reviews)

Inquire

from $275 / night

(35)

1 / 24

Key West House

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$275

Very Good (35 reviews)

Inquire

from $275 / night

(29)

1 / 23

Key West Apartment

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$230

Very Good (29 reviews)

Inquire

from $230 / night

(29)

1 / 24

Key West Cottage

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$215

Very Good (29 reviews)

Inquire

from $215 / night

(45)

1 / 24

Key West Studio

  • -1
  • 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$155

Very Good (45 reviews)

Inquire

from $155 / night

(4)

1 / 24

Key West House

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$805

Excellent (4 reviews)

Inquire

from $805 / night

(54)

1 / 24

Key West House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$345

Very Good (54 reviews)

Inquire

from $345 / night

(23)

1 / 24

Key West Apartment

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$235

Very Good (23 reviews)

Inquire

from $235 / night

(3)

1 / 22

Key West Apartment

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$190

Excellent (3 reviews)

Inquire

from $190 / night

(10)

1 / 24

Key West House

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$275

Excellent (10 reviews)

Inquire

from $275 / night

(28)

1 / 23

Key West Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$250

Very Good (28 reviews)

Inquire

from $250 / night

(3)

1 / 24

Key West House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$665

Very Good (3 reviews)

Inquire

from $665 / night

(16)

1 / 24

Key West House

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$290

Very Good (16 reviews)

Inquire

from $290 / night

(1)

1 / 25

Key West House

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$583

Excellent (1 reviews)

Inquire

from $583 / night

(26)

1 / 25

Key West House

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$230

Average (26 reviews)

Inquire

from $230 / night

(1)

1 / 24

Key West House

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly

$253

Excellent (1 reviews)

Inquire

from $253 / night

(27)

1 / 24

Key West House

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$315

Very Good (27 reviews)

Inquire

from $315 / night

(1)

1 / 24

Key West House

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

$245

Excellent (1 reviews)

Inquire

from $245 / night

(24)

1 / 24

Key West House

  • 3
  • 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$595

Very Good (24 reviews)

Inquire

from $595 / night

(11)

1 / 24

Key West Apartment

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$315

Very Good (11 reviews)

Inquire

from $315 / night

1 / 24

Key West Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $215 / night

(57)

1 / 24

Key West House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$345

Very Good (57 reviews)

Inquire

from $345 / night

1 / 24

Key West Apartment

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from $230 / night

(9)

1 / 23

Key West Apartment

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$330

Excellent (9 reviews)

Inquire

from $330 / night

(11)

1 / 24

Key West Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$235

Very Good (11 reviews)

Inquire

from $235 / night

(52)

1 / 28

Key West Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$215

Excellent (52 reviews)

Inquire

from $215 / night

1 / 24

Key West Apartment

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly

from $230 / night

(25)

1 / 24

Key West Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$205

Very Good (25 reviews)

Inquire

from $205 / night

(56)

1 / 24

Key West House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$240

Very Good (56 reviews)

Inquire

from $240 / night

About Key West

A laid-back city in the Florida Keys, Key West should be on every traveler's vacation list. With equal parts nature, history, and nightlife, this Florida destination has a little something for everyone.


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.
Read More