Historic Key West Vacation Rentals

Compare 60 vacation rentals.
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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 21 House rentals
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Condo rentals

View 18 Condo rentals
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Apartments

View 7 Apartments

Popular amenities for Historic Key West vacation rentals

Popular
Dog-friendly Hot tub Internet
Conch Casa
2 Bedroom | 1 Bath | Sleeps 6

Conch Casa - Key West, FL

$602 avg / night
4.51 (122)
Old Town Garden Villas - Abaco Suite
1 Bedroom | 1.5 Bath | Sleeps 4

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

$527 avg / night
4.71 (119)
Truman Suite #3
0 Bedroom | 1 Bath | Sleeps 2

Truman Suite #3 - Key West, FL

$240 avg / night
4.32 (158)
Old Town Garden Villas - Andros Suite
1 Bedroom | 1.5 Bath | Sleeps 4

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

$358 avg / night
4.74 (133)
Gardenia Getaway
2 Bedroom | 2 Bath | Sleeps 6

Gardenia Getaway - Key West, FL

$348 avg / night
4.75 (81)

View 55 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

Easy to walk to most things you likely want to do, but still back in the neighborhoods at bit, so it's pretty quiet at night. The photos are accurate and the property is taken care of nicely. Definitely would stay here again.
Daniel K. | Apr 2025
This place is so adorable and it’s perfectly located. Love that it was tucked away in its own special corner. Steps from a nice size pool. Will definitely stay here again!!
Catherine G. | Apr 2025
Perfect location and close to the wedding venue and everything else that everyone wanted to do. Plenty of room for everyone and we all had a wonderful time
Janice E. | Apr 2025
Historic Key West vacation rental FAQ

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. 60 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   |   Mallory Square - Key West   |   Old Town Key West   |   Bahama Village - Key West   |   Shipyard Condos - Key West   |   Duval Square - Key West   |   Key West   |   Florida
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