Historic Key West Vacation Rentals

Compare 46 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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Condo rentals

View 15 Condo rentals
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House rentals

View 15 House rentals
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Apartments

View 5 Apartments

Popular amenities for Historic Key West vacation rentals

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

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

$304 avg / night
(excludes fees and taxes)
4.73 (150)
Old Town Garden Villas - Abaco Suite
1 Bedroom | 1.5 Bath | Sleeps 4

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

$395 avg / night
(excludes fees and taxes)
4.66 (131)
Conch Casa
2 Bedroom | 1 Bath | Sleeps 6

Conch Casa - Key West, FL

$479 avg / night
(excludes fees and taxes)
4.47 (132)
Hemingway's View
3 Bedroom | 2 Bath | Sleeps 6

Hemingway's View - Key West, FL

$590 avg / night
(excludes fees and taxes)
4.41 (147)
Seagrass Suite
1 Bedroom | 1 Bath | Sleeps 2

Seagrass Suite - Key West, FL

$240 avg / night
(excludes fees and taxes)
4.74 (38)

View 41 more homes

Browse more vacation rental amenities in Historic Key West

Pool | Water view | Waterfront | A/C | Washer/dryer | Balcony | Bikes | Pack-N-Play | Beach access | Limited mobility access

Recent Historic Key West guest reviews

When originally booking this home, I read a lot of reviews good and bad on other platforms. Cleanliness and upkeep to an older cottage were the main recurring issues. I reached out to property management and they were careful enough in reassuring me of my concerns they responded by Email and phone months in advance of our reservation and were reachable just before and during our stay. None of the deficiencies I had come across in reviews over past years seem to still exist. Which tells me the owner and management pay attention and fix problems. Was a very clean and lovely stay. They best location. Very clean. Mind you, it isn't new. It's an older cottage. Vacasa office is across the street. They were very helpful with recommendations and holding our bags before check in and after check out. I think in general a 4 pm checkin could be 3pm and a 10 am check out could be an 11am. The cleaners were a little too eager. They were there at 9:55am already trying to get in when when we were still moving our suitcases to the front door.
Evan F. | Mar 2026
We absolutely loved our stay here in Key West! It was perfect for us and so incredibly cute—exactly the vibe we were hoping for. The bathroom was spacious and beautifully done, which made getting ready feel a little extra luxurious. The bed was amazing—super comfortable and honestly one of the best parts after long days of exploring. The kitchen was just what we needed. We didn’t do a ton of cooking, but having a fridge was a game changer for drinks, snacks, and leftovers. Everything felt clean, well-kept, and thoughtfully put together. The location was also great—close enough to everything we wanted to do, but still felt like a relaxing little escape. Overall, it was the perfect spot for our trip and we would definitely stay here again!
Morgan B. | Mar 2026
House is so cute and the decorations are very tasteful. Main concern for me was the fact that the back yard is not private but shared with other renters on the property. I brought lounge chairs to sit out in the backyard but when arrived an found out backyard was not private did not use the chairs. Location is close to Duval Street so easy to walk to anyplace. Top of the line appliances and the bathroon was gorgeous. Having an updated washer and dryer was an extra bonus. I would not rent again from this property due to the fact of no private backyard. If you do not need to use a backyard, than this is the place for you.
Sara A. | Mar 2026
Historic Key West vacation rental FAQ

Yes, 18 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. 46 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   |   Duval Square - Key West   |   Key West   |   Florida
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