Old Town Key West Vacation Rentals

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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).

Top Old Town Key West property types

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House rentals

View 20 House rentals
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Condo rentals

View 15 Condo rentals
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Cabins

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Popular amenities for Old Town Key West vacation rentals

Popular
Dog-friendly Hot tub Internet
Mermaid's Retreat
1 Bedroom | 1.5 Bath | Sleeps 2

Mermaid's Retreat - Key West, FL

$426 avg / night
(excludes fees and taxes)
4.48 (27)
Oceana Suite
1 Bedroom | 1 Bath | Sleeps 2

Oceana Suite - Key West, FL

$505 avg / night
(excludes fees and taxes)
4.78 (115)
Happy Hour Haven
2 Bedroom | 2 Bath | Sleeps 6

Happy Hour Haven - Key West, FL

$217 avg / night
(excludes fees and taxes)
4.53 (19)
Gardenia Getaway
2 Bedroom | 2 Bath | Sleeps 6

Gardenia Getaway - Key West, FL

$725 avg / night
(excludes fees and taxes)
4.71 (94)
Old Town Garden Villas - Abaco Suite
1 Bedroom | 1.5 Bath | Sleeps 4

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

$570 avg / night
(excludes fees and taxes)
4.66 (133)

View 45 more homes

Browse more vacation rental amenities in Old Town Key West

Pool | Ocean view | Water view | A/C | Fireplace | Washer/dryer | Balcony | Bikes | Golf on-site | Limited mobility access

Recent Old Town Key West guest reviews

Very spacious and comfortable home. Beautifully decorated and perfect for our needs. We used it as the place for my daughter and her wedding crew to get ready. Close to her venues and everything else. Vacasa service is always the best I have always stayed at their properties in Key West and have never had a complaint.
Marilyn M. | Apr 2026
It made you feel like you were in your own private paradise while being centrally located to Duval St.
Elizabeth P. | Mar 2026
The Bahama house was perfect for our family vacation. We had 6 adults and a toddler and plenty of space for all of us! The pool was lovely to have. The heater wasn't working the first day and the owner took care of it that day. The location was right off Duval street, a prime location!
Ellen W. | Mar 2026
Old Town Key West vacation rental FAQ

Yes, 17 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. 50 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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Old Town 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
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Seamless check-in
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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.

Nearby destinations

Gulf Coast   |   Florida's Atlantic Coast   |   South Florida   |   Southeast Florida   |   Florida Keys   |   Lower Keys, FL   |   Mallory Square - Key West   |   Bahama Village - Key West   |   Historic Key West   |   Papa's Hideaway - Key West, FL   |   Shipyard Condos - Key West   |   Key West   |   Florida
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