Historic Key West Vacation Rentals

Compare 75 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 condo rentals, house rentals, apartments, and more

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Condo rentals

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House rentals

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Apartments

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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

$166 avg / night
Yellowfin Ledge On Duval
1 Bedroom | 1 Bath | Sleeps 3

Yellowfin Ledge On Duval - Key West, FL

$223 avg / night
Amelia House
3 Bedroom | 2 Bath | Sleeps 8

Amelia House - Key West, FL

$617 avg / night
Hemingway's View
3 Bedroom | 2 Bath | Sleeps 8

Hemingway's View - Key West, FL

$647 avg / night
Truman @ Duval - Studio A
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Studio A - Key West, FL

$270 avg / night

View 70 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

So many things to do and see. Great food and lovely accommodation. 🥰
Lisa H. | Apr 2024
The unit was lovely. It was beautifully decorated and had two balconies which were great. We could have used a few more wine glasses and towels though! The neighborhood was quiet and convenient to the Hemingway house and other attractions although next to a couple of houses in disrepair which is really one of only two negatives with the other being that Mallory Square is a walk to get to. There is a cute art studio on the first floor of the building and this unit is only a short block to Duval Street which was perfect. We enjoyed our stay very much.
Diane C. | Apr 2024
Great little place in the Keys. Perfect location. Would definitely stay here again!!
Alice P. | Apr 2024
Historic Key West vacation rental FAQ

Yes, 32 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. 75 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.

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.

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
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