Old Town Key West Vacation Rentals

Compare 102 vacation rentals.
USA > Florida > Old Town Key West

Make Old Town Key West your next getaway

There’s just something special about staying in Old Town during your Key West vacation—and with our Old Key West rentals, you can do just that. This historic part of the Florida Keys includes many of the area’s most famous landmarks, like the iconic Hemingway House. The Conch Tour Train is a great way to explore the neighborhood with kids, but even if you don’t end up taking the train, the famous Southernmost Point is a must-see (and a great family photo opportunity).

Explore Old Town Key West condo rentals, house rentals, studios, and more

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Condo rentals

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House rentals

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Studios

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Old Town Key West vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Wahoo Way On Duval
1 Bedroom | 1 Bath | Sleeps 2

Wahoo Way On Duval - Key West, FL

$167 avg / night
Osprey Suite
1 Bedroom | 1 Bath | Sleeps 4

Osprey Suite - Key West, FL

$328 avg / night
Pelican Suite
1 Bedroom | 1 Bath | Sleeps 4

Pelican Suite - Key West, FL

$336 avg / night
Yellowfin Ledge On Duval
1 Bedroom | 1 Bath | Sleeps 3

Yellowfin Ledge On Duval - Key West, FL

$209 avg / night
Heron Suite
1 Bedroom | 1 Bath | Sleeps 4

Heron Suite - Key West, FL

$340 avg / night

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Browse more vacation rental amenities in Old Town Key West

Pool | Ocean view | Oceanfront | Water view | Waterfront | A/C | Elevator | Washer/dryer | Balcony | Bikes

Recent Old Town Key West vacation rental reviews

The place is fabulous! Location was the best for parking a car was private and quiet. The place was just perfect for 14 of us. I highly recommend for large groups. We would definitely come back here again. Maria
maria m. | Apr 2024
Great location.
Edward S. | Apr 2024
My stay at Passover Cottage in Key West was nothing short of fantastic! From the moment we arrived, the place felt like a private oasis. The highlight was definitely the pool area, which is well-maintained and offers a great escape from the daily hustle and bustle. It's like having your own tropical paradise! The cottage itself is well-equipped, with all the comforts of home, ensuring a comfortable stay without any hassle. The atmosphere is very relaxing, and the property is kept very clean and tidy. One of the best tips for future visitors is to rent a golf cart or scooter. It makes exploring Key West so much easier and adds a fun element to your travel. You can zip around to nearby attractions, shops, and restaurants with ease. Overall, if you’re looking for a tranquil and beautiful place to stay in Key West, Passover Cottage is the perfect choice. It's ideal for anyone wanting to unwind in a serene setting while being close enough to enjoy all that Key West has to offer. Highly recommended!
Norman G. | Apr 2024
Old Town Key West vacation rental FAQ

Yes, 47 of our Old Town 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. 102 of our Old Town 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 Old Town 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 Old Town 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 Old Town 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


Snorkeling in the crystal Caribbean waters is an ever-popular activity in Old Town, and Fort Zachary Taylor Park is a great launching point for your snorkeling adventures. Make the most of Key West’s sunsets during your vacation rental stay: head out to Mallory Square or Sunset Pier for community festivities (which often include street performers, conch fritters, and tiki drinks). Duval Street, the main drag in Old Town, is a fun spot to spend an afternoon shopping or an evening bar-hopping. If you’re daydreaming about a classic Old Town Key West beach bungalow, browse our selection and book your next getaway with Vacasa.

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