Key West Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Key West vacation homes

Beach

Summer special@ 129 Sun thru Wed.ngts lodging only 129 + extras

Summer special@ 129 Sun thru Wed.ngts lodging only 129 + extras
Old Town Key West
9.6 out of 10, Exceptional, (251 reviews)
"Loved our stay here!"
United States
Kristin E.
Summer special@ 129 Sun thru Wed.ngts lodging only 129 + extras
Outdoor dining

Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (66 reviews)
"We had a wonderful stay. The house was very clean, the area was quiet and peaceful, and the pool was incredibly relaxing. We enjoyed it so much that we have already booked another stay."
United States
Tiara B.
The price is CA $337
CA $562 total
includes taxes & fees
Jul 10 - Jul 11
Poolside Cottage #411
Terrace/patio

Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (16 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is CA $243
CA $698 total
includes taxes & fees
Jul 13 - Jul 14
Road's End | Prime Old Town Location! Updated Home w/ Pool
Outdoor dining

Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (31 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is CA $337
CA $562 total
includes taxes & fees
Jul 10 - Jul 11
Poolside Cottage #412
Pool

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
The price is CA $423
CA $868 total
includes taxes & fees
Jul 1 - Jul 2
Paradise found
Fridge, microwave, oven, dishwasher

Sea Esta Suite | Located On Iconic Duval w/ Pool

Sea Esta Suite | Located On Iconic Duval w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (47 reviews)
"Great stay! "
United States
Colleen S.
The price is CA $340
CA $1,165 total
includes taxes & fees
Jun 28 - Jun 29
Sea Esta Suite | Located On Iconic Duval w/ Pool
Terrace/patio

Atlantis House Suites

Atlantis House Suites
Midtown
10.0 out of 10, Exceptional, (3 reviews)
"Awesome place to stay ! Located just close enough and just far away enough . Highly recommended "
United States
Aaron J.
The price is CA $307
CA $898 total
includes taxes & fees
Jun 23 - Jun 24
Atlantis House Suites
Beach towels

Luxury two floor apartment in prime location of famous Duval Street

Luxury two floor apartment in prime location of famous Duval Street
Old Town Key West
9.6 out of 10, Exceptional, (102 reviews)
"Great place and location. The upstairs balcony was great for people watching. "
United States
Tracy M.
The price is CA $418
CA $1,022 total
includes taxes & fees
Jun 23 - Jun 24
Luxury two floor apartment in prime location of famous Duval Street
Property grounds

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Stock Island
10.0 out of 10, Exceptional, (23 reviews)
"Great place nice and clean easy access to the pool short drive to the beach"
United States
Nathan W.
The price is CA $446
CA $1,399 total
includes taxes & fees
Jun 23 - Jun 24
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Fridge, microwave, oven, stovetop

Casa Havana | Old Town Condo w/ Pool & Balcony

Casa Havana | Old Town Condo w/ Pool & Balcony
Old Town Key West
9.0 out of 10, Wonderful, (6 reviews)
"The property is very old, run down, furniture needs to be replaced, entire interior and trim needs to be repainted, paint chipped off of the majority of trim and molding, significant number of ants in both bedroom bathrooms, mattresses need to be replaced as they are soft and worn out, and not least of all, the property manager has hidden the thermostat underneath an alarm cover, seemingly to prevent guests from lowering the temperature."
United States
John B.
The price is CA $373
CA $1,031 total
includes taxes & fees
Jul 15 - Jul 16
Casa Havana | Old Town Condo w/ Pool & Balcony
Terrace/patio

Southernmost Retreat | On Duval! With Hot Tub, Patio

Southernmost Retreat | On Duval! With Hot Tub, Patio
Old Town Key West
9.8 out of 10, Exceptional, (29 reviews)
"Fantastic location. Perfect spot for being in and out on Duval Street. "
United States
Stephen S.
The price is CA $445
CA $1,384 total
includes taxes & fees
Jun 28 - Jun 29
Southernmost Retreat | On Duval! With Hot Tub, Patio
Terrace/patio

Passover Cottage | Private Pool & Ideal Key West Location

Passover Cottage | Private Pool & Ideal Key West Location
Old Town Key West
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful, clean property. Good location. Great stay, would absolutely stay again. Highly, recommended!!"
United States
john w.
The price is CA $459
CA $1,151 total
includes taxes & fees
Jun 28 - Jun 29
Passover Cottage | Private Pool & Ideal Key West Location
Interior

3-bedroom townhome in Key West with fitness room, WiFi

3-bedroom townhome in Key West with fitness room, WiFi
Stock Island
9.8 out of 10, Exceptional, (13 reviews)
"The unit was clean and comfortable. Had everything that we needed for our stay. Close to Key West and everything we wanted to do. "
United States
Trisha K.
The price is CA $646
CA $1,536 total
includes taxes & fees
Jun 23 - Jun 24
3-bedroom townhome in Key West with fitness room, WiFi
A heated pool

Key West Lighthouse Suite

Key West Lighthouse Suite
Old Town Key West
9.8 out of 10, Exceptional, (61 reviews)
"Great location and pool area was relaxing."
United States
Andy S.
The price is CA $892
CA $1,450 total
includes taxes & fees
Jun 24 - Jun 25
Key West Lighthouse Suite
Outdoor pool

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Key West Historic District
10.0 out of 10, Exceptional, (125 reviews)
"Great little house for a family "
United States
Edward M.
The price is CA $764
CA $1,943 total
includes taxes & fees
Jun 23 - Jun 24
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Property grounds

Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St

Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Old Town Key West
9.4 out of 10, Exceptional, (51 reviews)
"Great location and we would stay here again. "
United States
Brandon A.
The price is CA $687
CA $1,588 total
includes taxes & fees
Jul 6 - Jul 7
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
Pool

Private Parking, Heated Pool - Sweet Caroline

Private Parking, Heated Pool - Sweet Caroline
Key West Historic District
9.0 out of 10, Wonderful, (32 reviews)
"Great place for our party and great host!"
United States
Jenny R.
The price is CA $541
CA $1,118 total
includes taxes & fees
Jul 7 - Jul 8
Private Parking, Heated Pool - Sweet Caroline
Pool

Spacious 3-bedroom townhome on Stock Island with resort style pool.

Spacious 3-bedroom townhome on Stock Island with resort style pool.
Stock Island
10.0 out of 10, Exceptional, (6 reviews)
"Location, pool, comfy beds. Will definitely return and recommend to others "
United States
janet n.
The price is CA $565
CA $1,047 total
includes taxes & fees
Jul 12 - Jul 13
Spacious 3-bedroom townhome on Stock Island with resort style pool.
Beach

Steps to Duval •Hot tub • Sleeps 6

Steps to Duval •Hot tub • Sleeps 6
Old Town Key West
9.8 out of 10, Exceptional, (18 reviews)
"Perfect location parking is a plus and being put friendly as a plus"
United States
Kat B.
The price is CA $544
CA $1,004 total
includes taxes & fees
Jun 23 - Jun 24
Steps to Duval •Hot tub • Sleeps 6
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Key West Hotel Reviews

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

8/10 Good
"Very nice hotel, the breakfast was good, beds were comfortable, room was clean and smelled nice. They do charge a $25 fee per day but they make up for it by providing two non alcoholic beverages, free parking, free shuttle to downtown and the use of a cooler, umbrella and beach towels for a day at the beach. The only negative thing I would say is the pool water was too warm, not cool and refreshing. I would definitely stay again."
Virginia 2-night trip
Posted less than an hour ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Find out more about Key West

Key West Vacation Homes information

Number of reviews
682
Accommodation
923 Vacation Homes
Lowest Price
CA $562
Highest Price
CA $1,943

Explore a world of travel with Expedia