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 102 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


Condo rentals

View 41 Condo rentals

House rentals

View 28 House rentals


View 16 Studios

Old Town Key West vacation rentals for every getaway

Dog-friendly Hot tub Internet
Audubon House 3D Tour
1 Bedroom | 2 Bath | Sleeps 4

Audubon House - Key West, FL

From $163
Truman Suite 3D Tour
0 Bedroom | 1 Bath | Sleeps 2

Truman Suite - Key West, FL

From $111
Passover Cottage 3D Tour
2 Bedroom | 2 Bath | Sleeps 4

Passover Cottage - Key West, FL

From $430
Tropical Village - Poolside Paradise 3D Tour
0 Bedroom | 1 Bath | Sleeps 2

Tropical Village - Poolside Paradise - Key West, FL

From $126
Truman @ Duval - Studio A 3D Tour
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Studio A - Key West, FL

From $152

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Recent Old Town Key West vacation rental reviews

I visited Papa’s with girlfriends and it was the perfect island gem! The main cottage was great for morning coffees on the back deck and the shaded pool was great for afternoon beverages and a cool swim after a hot day. The apartments were high quality and equipped with everything you need for a restful vacation! Highly recommend!!
309 Louisa St LLC R. | May 2022
Great location, can walk to best restaurants and bars on Duval. Pool was warm and never too crowded. House was clean and had everything we needed.
Robert Z. | May 2022
This little place was a great location. Walking distance to the popular sites. a great little cuban place on the corner. I loved that the cottage was not on the main street, but hidden behind some other buildings. The cottage was clean and comfortable. We could hear a little noise, but it was never a big deal and we still slept great. Would highly recommend.
Toni S. | May 2022

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.