Historic Key West Vacation Rentals

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Make Historic Key West your next getaway—choose from 71 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 22 House rentals


View 5 Studios

Historic Key West vacation rentals for every getaway

Dog-friendly Hot tub Internet
Passover Cottage 3D Tour
2 Bedroom | 2 Bath | Sleeps 4

Passover Cottage - Key West, FL

From $430
Old Town Garden Villas - Andros Suite 3D Tour
1 Bedroom | 1.5 Bath | Sleeps 4

Old Town Garden Villas - Andros Suite - Key West, FL

From $173
Hemingway's View 3D Tour
3 Bedroom | 2 Bath | Sleeps 8

Hemingway's View - Key West, FL

From $472
Oceana Suite 3D Tour
1 Bedroom | 1 Bath | Sleeps 4 (2 Adults Max)

Oceana Suite - Key West, FL

From $360
Audubon House 3D Tour
1 Bedroom | 2 Bath | Sleeps 4

Audubon House - Key West, FL

From $163

View 66 more homes

Recent Historic Key West vacation rental reviews

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
The place was perfect for my husband and—plenty of room for two; adequate storage for belongings, if needed; clean, which is really important to us; and a comfortable bed. We loved having the good sized mini fridge! If I could make one suggestion for those of us who have to have our kids manage our technology and electronics—please leave instructions on how to coordinate using the television and DirecTv.
Lisa G. | May 2022
So cute, great size for 2 people and absolute perfect location
Lillie C. | 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.