Historic Key West Vacation Rentals

Compare 76 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 condo rentals, house rentals, apartments, and more

Condo rentals

View 29 Condo rentals

House rentals

View 24 House rentals

Apartments

View 7 Apartments

Popular amenities for Historic Key West vacation rentals

Popular

Dog-friendly Hot tub Internet

Wahoo Way On Duval

1 Bedroom | 1 Bath | Sleeps 2

Wahoo Way On Duval - Key West, FL

$161 avg / night

Yellowfin Ledge On Duval

1 Bedroom | 1 Bath | Sleeps 3

Yellowfin Ledge On Duval - Key West, FL

$188 avg / night

Hemingway's View

3 Bedroom | 2 Bath | Sleeps 8

Hemingway's View - Key West, FL

$811 avg / night

3 Bedroom | 2 Bath | Sleeps 8

Amelia House - Key West, FL

$716 avg / night

Truman @ Duval - Studio A

0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Studio A - Key West, FL

$284 avg / night

View 71 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

We always enjoy renting a space that is larger than we need. This is a large 2/2 that gives a wonderful view of the water. Beautiful sunsets right off the balcony. It was updated and very clean. There are no staples in the kitchen except salt and pepper along with Folgers in filter packs. We didn't rent a car and everything you need is accessible with lots of restaurant options. We did rent a golf cart for 24hrs mid-week and toured the island and went to the Publix and bought a couple of days of meals to cook. We went to Fausto's and CVS a couple of times as well for conveniences. Things to note: Use the pool key to access the pool AND the back gate to the waterfront. In order to get into the back gardens and walkway, you need to access the pool area through the garage or go into 115 to get outside to the back gate. The key on the ring with the fob will work on the Truman access gate (one side) on Caroline Street. Our key didn't work on the other gates we tried. If you don't know about the back gate or the Caroline gate key, you will have to walk the long way around through the Southard entrance after 6pm. That is when the gates are closed. This was a bummer on day one because we hadn't figured out the key access. All said, I loved walking through Truman Annex. It is a pure oasis from the noise and crowds of the waterfront and Duval. Our week was great and we will rent again!!

Valeska B. | May 2024

We loved it the room. Very good treatment from Vacasa. Our expectations were met.

Enrique G. | May 2024

I picked this unit for the price and location, and both were wonderful. I found the unit to be cozy, clean, and welcoming. The hosts were available by text message, which was great for me. I would absolutely stay here again.

Molly P. | May 2024

Historic Key West vacation rental FAQ

Yes, 32 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).

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Yes. 76 of our Historic Key West vacation rentals have internet access, so you can stay connected throughout your trip.

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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

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