Historic Key West Vacation Rentals

Compare 36 vacation rentals.
Home > USA > Florida > Historic Key West

Make Historic Key West your next getaway

On your next trip to the Florida Keys, why not sightsee in the sunshine? Historic Key West vacation rentals open the door to the city’s oldest district, home to everything from antique stores to ghost tours. Stroll downtown and grab a slice of key lime pie between trips to the beach.

Top Historic Key West property types

housing_type_house.jpg

House rentals

View 14 House rentals
housing_type_condo.jpg

Condo rentals

View 12 Condo rentals
housing_type_cabin.jpg

Cabins

View 4 Cabins

Browse more vacation rental amenities in Historic Key West

Pool | Water view | Waterfront | A/C | Fireplace | Washer/dryer | Bikes | Golf on-site | Beach access | Snowbird-friendly

Popular amenities for Historic Key West vacation rentals

Popular
Dog-friendly Hot tub Internet
KW31C - Jasmine Suite
1 Bedroom | 1 Bath | Sleeps 4

KW31C - Jasmine Suite - Key West, FL

$542 avg / night
(excludes fees and taxes)
4.51 (101)
KW33A - Leeward Isle
2 Bedroom | 1 Bath | Sleeps 6

KW33A - Leeward Isle - Key West, FL

$694 avg / night
(excludes fees and taxes)
4.45 (82)
KW37 - Oceana Suite
1 Bedroom | 1 Bath | Sleeps 2

KW37 - Oceana Suite - Key West, FL

$505 avg / night
(excludes fees and taxes)
4.78 (115)
KW378FLR - Periwinkle Place
1 Bedroom | 1 Bath | Sleeps 4

KW378FLR - Periwinkle Place - Key West, FL

$161 avg / night
(excludes fees and taxes)
5.0 (1)
KW370FLR - Paradise on Packer
2 Bedroom | 1 Bath | Sleeps 4

KW370FLR - Paradise on Packer - Key West, FL

$165 avg / night
(excludes fees and taxes)
5.0 (4)

View 31 more homes

Recent Historic Key West guest reviews

The house was great! We spent 2 months there. It was an easy walk to everything. The kitchen was very nice and very well stocked. There was a very nice webber grill by the pool that we used a lot. The pool had someone come once a week to clean and check the water. There was also a lawn person to maintain the yard and pool deck. There were plenty of towels and linens. It is located on one of the main bike routes and a historic cemetery is about a block away.
Donna F. | Apr 2026
Lovely little unit perfect for a couple. Right in the middle of the island - we walked to everything! Enjoy!!!
Sandra S. | Apr 2026
Very spacious and comfortable home. Beautifully decorated and perfect for our needs. We used it as the place for my daughter and her wedding crew to get ready. Close to her venues and everything else. Vacasa service is always the best I have always stayed at their properties in Key West and have never had a complaint.
Marilyn M. | Apr 2026
Historic Key West vacation rental FAQ

Yes, 14 of our Historic Key West homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 36 of our Historic Key West vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Historic Key West vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Historic Key West team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Historic Key West, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning


Explore our Historic Key West, FL, vacation rentals

Historic Key West is the island’s oldest district, spanning 4,000 acres and including 187 historic buildings. Step back in time while walking through homes and museums dating back to the 1800s, or zip through the streets by an old-fashioned trolley tour. Must-see stops while you visit are the Key West Lighthouse and the Southernmost Point Buoy, which marks the farthest point of the continental United States at just 90 miles from Cuba.

Head to Fort Zachary Taylor Historic State Park Beach for excellent swimming and snorkeling, with a rental hut nearby for any equipment you might need. If you’re traveling with kids, don’t miss The Key West Butterfly and Nature Conservatory and the Key Lime Pie Bakery. Set off for a new adventure in the Sunshine State in a Historic Key West house rental.

Nearby destinations

Gulf Coast   |   Florida's Atlantic Coast   |   South Florida   |   Southeast Florida   |   Florida Keys   |   Lower Keys, FL   |   Old Town Key West   |   Mallory Square - Key West   |   Bahama Village - Key West   |   Shipyard Condos - Key West   |   Key West   |   Florida
Show more