Historic Key West Vacation Rentals

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USA > Florida > Historic Key West

Make Historic Key West your next getaway—choose from 70 great vacation rentals

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.

Explore Historic Key West condo rentals, house rentals, studios, and more


Condo rentals

View 30 Condo rentals

House rentals

View 21 House rentals


View 5 Studios

Historic Key West vacation rentals for every getaway

Dog-friendly Hot tub Internet
Yellowfin Ledge On Duval 3D Tour
1 Bed | 1 Bath | Sleeps 3

Yellowfin Ledge On Duval - Key West, FL

From $164
Audubon House 3D Tour
1 Bed | 2 Bath | Sleeps 4

Audubon House - Key West, FL

From $204
Truman @ Duval - Studio A 3D Tour
0 Bed | 1 Bath | Sleeps 2

Truman @ Duval - Studio A - Key West, FL

From $163
The Frontier Flat 3D Tour
1 Bed | 1 Bath | Sleeps 4

The Frontier Flat - Key West, FL

From $206
Truman Suite 3D Tour
0 Bed | 1 Bath | Sleeps 2

Truman Suite - Key West, FL

From $135

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Recent Historic Key West vacation rental reviews

Walk to the best restaurants and must-see attractions. The house is newly renovated and bathrooms are beautiful. We enjoyed the garden
KRE Admiral, LLC L. | May 2022
Gardenia Getaway was a great place - very close to everything yet the street was very quiet. Be aware to bring plastic forks, etc with you - there are none there. Just a couple mugs & a few glasses. No plates or anything else. Otherwise this was a great place - perfect size for 2 people!
Dawn C. | May 2022
Great location, can walk to best restaurants and bars on Duval. Pool was warm and never too crowded. House was clean and had everything we needed.
Robert Z. | May 2022

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional 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.