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

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Popular amenities for Historic Key West vacation rentals

Popular
Dog-friendly Hot tub Internet
Windward Isle
2 Bedroom | 1 Bath | Sleeps 6

Windward Isle - Key West, FL

$624 avg / night
4.32 (41)
Truman @ Duval - Unit F
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Unit F - Key West, FL

$342 avg / night
4.23 (31)
Truman @ Duval - Studio A
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Studio A - Key West, FL

$365 avg / night
4.4 (48)
Leeward Isle
2 Bedroom | 1 Bath | Sleeps 6

Leeward Isle - Key West, FL

$552 avg / night
4.52 (60)
Orchid Suite
1 Bedroom | 1 Bath | Sleeps 4

Orchid Suite - Key West, FL

$305 avg / night
4.55 (73)

View 57 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

Just finished a quick stay, and enjoyed everything. Love the access to Duval Street. They’ve done a great job with the house and we plan to stay again but longer this time.
Kevin C. | Jan 2025
What a wonderful spot for a couple to spend their downtime to recharge while out and about in Key West. It was a perfect spot to take a nap, whip up a meal, or just relax in the A/C while reading a book. This property sits back with a private, gated entry which makes it feel more secluded and private. Wonderful spot for two to enjoy their time together.
James F. | Jan 2025
The home was beautiful and accurate in description and photos. Quiet residential area with its location basically in the center of Old Town which makes it very walkable to any point in the area. Will definitely look into staying here again the next time we want to spend a few days in Key West.
Gary M. | Jan 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. 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.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
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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
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