A two-story house with green shutters and a wooden balcony.

Key West Historic District vacation rentals

We found 1,681 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Key West Historic District by choosing from 676 houses, 209 apartments, and other vacation rentals. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include parking and a hot tub. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

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Find properties near top attractions in Key West Historic District

A street with a pharmacy, a theater, and a yellow building.

Duval Street

Mallory Square

A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.

Ernest Hemingway Home and Museum

A butterfly on a plant with green leaves and yellow flowers.

Key West Butterfly and Nature Conservatory

A historical marker for The Little White House, built in 1890, used by American Navy officers, and listed on the National Register of Historic Places in 1974.

Harry S. Truman Little White House

A lighthouse with a white exterior and a black top, surrounded by lush green trees.

Key West Lighthouse and Keeper's Quarters Museum

A yellow exhibit labeled 'NOAA's AQUARIUS UNDERSEA LAB' with a circular window and a door.

Florida Keys Eco - Discovery Center

A cozy living room with a wooden floor, a sofa, a table with chairs, a lamp, and a ship model on top of a cabinet.

Oldest House Museum and Garden

A historic building with maritime museum banners, a rusty boat, and a tree-lined street.

Mel Fisher Maritime Museum

A historic building with a tall tower, palm trees, and a vintage trolley.

Key West Shipwreck Museum

Find the best place to stay - Key West Historic District

3-bedroom house boat in tranquil Key West with AC

Sleeps 10 · 3 bedrooms · 2+ bathrooms

Premier Host

Steps from Duval, Pool on Site & Bikes Included!

Sleeps 2 · 1 bathroom

Premier Host

Penthouse Waterfront Dock Pool Condo Near Duval St

Sleeps 16 · 4 bedrooms · 4 bathrooms

Hatteras Sleeps 8 & SelfDrive 20' Pontoon Fishing Lobstering Snorkeling Sandbar

Sleeps 10 · 3 bedrooms · 2+ bathrooms

Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

Sleeps 4 · 2 bedrooms · 2 bathrooms

JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!

Sleeps 4 · 2 bedrooms · 1 bathroom

Top rated rentals - Key West Historic District

Image of Old Town Elegance Island Breezes and Poolside Bliss

Excellent Service by Julia

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: I have stayed at Varela Dreaming and dealt with Julia a couple of times now. The service is excellent and quick if there are any queries. The house is lovely, very homely and clean. Great location, nice neighbours, private garden. I love sitting on the porch in the morning and early evening. It was also nice to see the umbrella I left in the garden is still there to be used too. I have reserved again for next year too. Thanks again Julia for a lovely stay.

Karen L.

Stayed May 2025

Image of MONTHLY Rental, JAN, FEB, MAR 2027 just opened, Old Town, pets ok

Modern "Old Town" Charm

We loved our stay in Sea Monkey! The 2 bedroom, 2 bath upper unit was supremely comfortable with central air and large beautifully decorated bedrooms with excellent mattresses. We especially enjoyed watching palm trees in the breeze against the background of a clear blue sky while playing games and enjoying dinner outside on the covered back deck. The great location afforded us an easy walk or bike ride to all that Key West has to offer. We couldn't imagine a better host than Marla. Thank you!

Page W.

Stayed Jan 2025

Image of NEWTON'S NEST ~ Adult Only, 1st Floor 1 Bedroom, 1 Bath Condo w/ Shared Pool!

Excellent place to stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: clean ,quiet , nicley decorated and the host and managers were had excellent communication.I highly recommend staying here to enjoy your Key West experience.

Russ B.

Stayed Dec 2023

Image of Sanctuary Adorable Gated Loft Studio Old Town Close to Duval - Location Location

December 2023 Stay

Wonderful stay!. This place has everything you need - I ate out most of the time, but all the cooking, etc was there. Also toaster, blender, coffee maker, ice maker, even a wine fridge. This place was cute and had a great little patio area where you can enjoy a cocktail or just sit and enjoy the weather. The apartment complex has 6 units and it is fully fenced in with a coded entry door. There are very pretty gardens all around the apartments. Since I am a bit elderly and didn't think the loft bedroom would be good for me, the owners made up the futon bed for me with a nice comfy topper. Very comfortable! Quiet neighborhood. Two blocks from Duval and very close to the CVS and nice restaurants, Loved my stay. It was perfect. I plan on returning again.

Julie D.

Stayed Dec 2023

Image of Key West Cottage Located in Old Town Key West. Available February 2026-on!!!!

Key West Stay

A quaint Key West cottage with lot’s of charm. On site parking is a major plus.

Skip W.

Stayed Jan 2019

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Frequently asked questions

How much does it cost to rent a vacation rental in Key West Historic District?

A number of factors influence how much you pay for a vacation rental in Key West Historic District, like the time of year, length of stay and property type. But, all Vrbo homes have something in common — incredible value. Simply add your travel dates to find your perfect fit.

How much does it cost to rent a beach house in Key West Historic District?

Prices for beach houses in Key West Historic District can differ depending on the size and type of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and the number of guests to view vacation rental options and prices. From there you can use our filters to narrow your search results by nearby activities, ratings, amenities and more.

What are the top attractions for families in Key West Historic District?

Keep the kids amused at these popular family-friendly attractions in Key West Historic District:

Nancy Forrester's Secret Garden
Duval Street
Donkey Milk House

How old do you have to be to rent a vacation rental in Key West Historic District?

The minimum age requirements can differ between properties on Vrbo, so double-check the rules of the vacation home in Key West Historic District you want to book. But usually, it's 16, 18 or 21.

How long can I rent a vacation rental in Key West Historic District for?

The amount of time you can book a Key West Historic District vacation home for depends on each property. Simply put in your travel dates to see available options that offer extended stays. They come with all you require to make your extended getaway more convenient and comfortable, like kitchens and yards. Some vacation rentals may also offer weekly or monthly discounts, so you can have a longer stay for less.

Does Vrbo offer discounts for vacation homes in Key West Historic District?

Overnight trip or a well-deserved long vacation, Vrbo has some great deals and discounted options in Key West Historic District to match your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or see what's just been added with one of our newly listed homes. Whatever kind of getaway you're after, you'll find the perfect place to stay — at an affordable rate.

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