Historic Key West Vacation Rentals

Compare 39 vacation rentals.
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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.

Top Historic Key West property types

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House rentals

View 14 House rentals
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Condo rentals

View 13 Condo rentals
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Cabins

View 4 Cabins

Popular amenities for Historic Key West vacation rentals

Popular
Dog-friendly Hot tub Internet
The Conch-Out Cottage
1 Bedroom | 2 Bath | Sleeps 5

The Conch-Out Cottage - Key West, FL

$169 avg / night
(excludes fees and taxes)
5.0 (5)
Conched Out Cottage
2 Bedroom | 1 Bath | Sleeps 6

Conched Out Cottage - Key West, FL

$175 avg / night
(excludes fees and taxes)
5.0 (9)
Paradise Suite
1 Bedroom | 1.5 Bath | Sleeps 2

Paradise Suite - Key West, FL

$150 avg / night
(excludes fees and taxes)
4.5 (6)
Casa Del Sol
2 Bedroom | 1 Bath | Sleeps 6

Casa Del Sol - Key West, FL

$334 avg / night
(excludes fees and taxes)
5.0 (3)
Orchid Suite
1 Bedroom | 1 Bath | Sleeps 4

Orchid Suite - Key West, FL

$344 avg / night
(excludes fees and taxes)
4.48 (87)

View 34 more homes

Browse more vacation rental amenities in Historic Key West

Pool | Water view | A/C | Fireplace | Washer/dryer | Balcony | Bikes | Golf on-site | Limited mobility access | Enclosed yard

Recent Historic Key West guest reviews

We enjoyed our first stay at Key West and at Baya House! Beautifully decorated, clean, and comfortable. The grounds are beautifully maintained and the pool area is so accessible and well cared for. We enjoyed our afternoons of sunning and swimming after our morning explorations. Walking distance to just about everything and the off street parking a huge plus! Would definitely stay again!
Dawn L. | Apr 2026
Very spacious and comfortable home. Beautifully decorated and perfect for our needs. We used it as the place for my daughter and her wedding crew to get ready. Close to her venues and everything else. Vacasa service is always the best I have always stayed at their properties in Key West and have never had a complaint.
Marilyn M. | Apr 2026
It made you feel like you were in your own private paradise while being centrally located to Duval St.
Elizabeth P. | Mar 2026
Historic Key West vacation rental FAQ

Yes, 16 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. 39 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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Historic Key West, log in to Trip Manager to explore the 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   |   Key West   |   Florida
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