Historic Key West Vacation Rentals

Compare 69 vacation rentals.
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.

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

housing_type_house.jpg

House rentals

View 25 House rentals
housing_type_condo.jpg

Condo rentals

View 22 Condo rentals
housing_type_apartment.jpg

Apartments

View 7 Apartments

Popular amenities for Historic Key West vacation rentals

Popular
Dog-friendly Hot tub Internet
Wahoo Way On Duval
1 Bedroom | 1 Bath | Sleeps 2

Wahoo Way On Duval - Key West, FL

$206 avg / night
4.52 (64)
Amelia House
3 Bedroom | 2 Bath | Sleeps 8

Amelia House - Key West, FL

$779 avg / night
4.37 (102)
Hemingway's View
3 Bedroom | 2 Bath | Sleeps 8

Hemingway's View - Key West, FL

$952 avg / night
4.5 (120)
Truman @ Duval - Studio A
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Studio A - Key West, FL

$304 avg / night
4.38 (45)
Truman @ Duval - Unit E
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Unit E - Key West, FL

$282 avg / night
4.21 (38)

View 64 more homes

Browse more vacation rental amenities in Historic Key West

Pool | Ocean view | Oceanfront | Water view | Waterfront | A/C | Elevator | Washer/dryer | Balcony | Bikes

Recent Historic Key West guest reviews

Cute clean house. The house was comfortable. Nice front porch and back yard deck and hot tub. The hot tub water was green and didn't get treated durung our 2 night stay. Driveway is long and narrow, but we managed it with a minivan.
Craig H. | Nov 2024
Perfect for our group of 6 - Three bedrooms and 3 Baths. Such a cute and comfortable little gem. Highly recommend
Mickie E. | Nov 2024
Perfect for 2 couples in key west if you are very close. 2 bathrooms made it perfect to get up, shower and get out there and have fun. A little tight for space, but if you plan on spending a lot of time in the unit, you are doing key west wrong! Would stay here again in a heartbeat.
Christopher R. | Nov 2024
Historic Key West vacation rental FAQ

Yes, 29 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. 69 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 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 worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Historic Key West, log in to Trip Manager to see 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   |   Duval Square - Key West   |   Key West   |   Florida
Show more