Historic Key West Vacation Rentals

Compare 53 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 19 House rentals
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Condo rentals

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Apartments

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Historic Key West vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Old Town Garden Villas - Andros Suite
1 Bed | 1.5 Bath | Sleeps 4

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

$501 avg / night
(excludes fees and taxes)
4.75 (138)
Key Lime Calypso
2 Bed | 1 Bath | Sleeps 6

Key Lime Calypso - Key West, FL

$1,248 avg / night
(excludes fees and taxes)
4.54 (110)
Casa Havana at Duval Square R22
2 Bed | 2.5 Bath | Sleeps 6

Casa Havana at Duval Square R22 - Key West, FL

$838 avg / night
(excludes fees and taxes)
4.26 (87)
Old Town Garden Villas - Abaco Suite
1 Bed | 1.5 Bath | Sleeps 4

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

$721 avg / night
(excludes fees and taxes)
4.72 (122)
Leeward Isle
2 Bed | 1 Bath | Sleeps 6

Leeward Isle - Key West, FL

$355 avg / night
(excludes fees and taxes)
4.49 (71)

View 48 more homes

Recent Historic Key West vacation rental reviews

Great Location
Thomas S. | Jun 2025
Visiting Key West for the first time, I wanted to stay somewhere right in the heart of the action—and Key to Paradise delivered and then some. Just a short walk from Duval Street, the location couldn’t have been more ideal. Everything I needed was close by, including a CVS just minutes away for any essentials—though I hardly needed anything extra, as the home was incredibly well-stocked and accommodating. One of the best parts about the location was the number of restaurants within walking distance. From casual bites to upscale dining, there was no shortage of amazing food options just steps away. Whether I was in the mood for seafood, Cuban cuisine, or just a good cup of coffee, everything was right around the corner. The home itself was thoughtfully designed for both comfort and fun. There were plenty of rooms to choose from, each with its own charm, and the colorful island-inspired decor brought a cheerful, vacation-ready energy to the entire space. In the evenings, I loved relaxing in either of the two cozy living rooms—both equipped with smart TVs that made it easy to stream all my favorite shows. During the day, the full kitchen had everything I needed to whip up meals, snacks, or a quick breakfast before heading out to explore. The property also featured a spacious layout indoors and outdoors, including a separate guest house and a refreshing pool—perfect for unwinding after a day of adventures. The neighborhood felt safe and walkable, which made getting around a breeze. Key to Paradise truly made my trip unforgettable. I couldn’t have asked for a better place to stay and will absolutely be booking again on future visits. Key West was amazing, and this home made it all the more special.
Jake S. | Jun 2025
This is our second time renting this condo. We liked is so much the first time we sought it out on our second visit. It is clean and has everything you could possibly need to cook, do laundry, lounge around, whatever you want. Having two bathrooms is a huge plus. The location is fantastic, minutes from everything. Couldn't be happier. When we come back, we will definitely seek out Shipyard Perch again.
Diane E. | Jun 2025
Historic Key West Frequently Asked Questions

Yes, 20 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. 53 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.