Old Town Key West Vacation Rentals

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USA > Florida > Old Town Key West

Make Old Town Key West your next getaway—choose from 133 great vacation rentals

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

View 47 Condo rentals
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House rentals

View 30 House rentals
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Studios

View 29 Studios

Old Town Key West vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Tropical Village - Utopia 3D Tour
2 Bed | 1 Bath | Sleeps 4

Tropical Village - Utopia - Key West, FL

From $269
Wahoo Way On Duval 3D Tour
1 Bed | 1 Bath | Sleeps 2

Wahoo Way On Duval - Key West, FL

From $287
Tropical Retreat 3D Tour
3 Bed | 3.5 Bath | Sleeps 8

Tropical Retreat - Key West, FL

From $551
Old Town Garden Villas - Little Havana Suite 3D Tour
1 Bed | 1.5 Bath | Sleeps 4

Old Town Garden Villas - Little Havana Suite - Key West, FL

From $256
Old Town Garden Villas - Andros Suite 3D Tour
1 Bed | 1.5 Bath | Sleeps 4

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

From $157

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Recent Old Town Key West vacation rental reviews

We enjoyed being in the middle of the action. Steps to Duval street and a short walk to Hemingway house. Kitchen had all of our needs. Living room and master bedroom were spacious. Hot tub was enjoyed after a long walk to enjoy the sights. Condo is right at a stop for the free Duval Loop bus and we used it many times.
Lynn W. | Oct 2021
The solitude, was very nice and peaceful, we loved the room, very clean place, we enjoyed the pool and privacy! Would highly recommend the rental!!
Margaret M. | Oct 2021
Condo was great! Clean, spacious, great location!
Kellie G. | Oct 2021

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 book your next getaway with Vacasa.