Historic Key West Vacation Rentals

Compare 62 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

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House rentals

View 22 House rentals
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Condo rentals

View 19 Condo rentals
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Apartments

View 7 Apartments

Explore more vacation rental amenities in Historic Key West

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

Historic Key West vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Hemingway's View
3 Bed | 2 Bath | Sleeps 8

Hemingway's View - Key West, FL

$1,641 avg / night
4.5 (121)
Amelia House
3 Bed | 2 Bath | Sleeps 8

Amelia House - Key West, FL

$1,316 avg / night
4.33 (105)
Truman @ Duval - Studio A
0 Bed | 1 Bath | Sleeps 2

Truman @ Duval - Studio A - Key West, FL

$515 avg / night
4.38 (47)
Orchid Suite
1 Bed | 1 Bath | Sleeps 4

Orchid Suite - Key West, FL

$463 avg / night
4.54 (72)
Truman @ Duval - Unit E
0 Bed | 1 Bath | Sleeps 2

Truman @ Duval - Unit E - Key West, FL

$465 avg / night
4.21 (39)

View 57 more homes

Recent Historic Key West vacation rental reviews

Duval Street was not even 60s away and Hemingway House was literally around the corner
Dave M. | Dec 2024
Clean, walking distance to lower Duval 20 minutes . Vacasa office right around the corner. No parking!!!. Nice kitchen no table inside. Beautiful decks on both floors. Close to hop on hop off stops. Would stay again.
Perry R. | Dec 2024
The property was nice and clean. The TV's were the issue and the pool was cold.
Kelly H. | Dec 2024
Historic Key West Frequently Asked Questions

Yes, 22 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. 62 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.

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