Old Town Key West Vacation Rentals

Compare 82 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 house rentals, condo rentals, studios, and more

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House rentals

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Condo rentals

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Studios

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Popular amenities for Old Town Key West vacation rentals

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

Wahoo Way On Duval - Key West, FL

$206 avg / night
4.52 (64)
Amelia House
3 Bedroom | 2 Bath | Sleeps 8

Amelia House - Key West, FL

$779 avg / night
4.37 (102)
Hemingway's View
3 Bedroom | 2 Bath | Sleeps 8

Hemingway's View - Key West, FL

$952 avg / night
4.5 (120)
Truman @ Duval - Studio A
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Studio A - Key West, FL

$304 avg / night
4.38 (45)
Truman @ Duval - Unit E
0 Bedroom | 1 Bath | Sleeps 2

Truman @ Duval - Unit E - Key West, FL

$282 avg / night
4.21 (38)

View 77 more homes

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 guest reviews

Cute clean house. The house was comfortable. Nice front porch and back yard deck and hot tub. The hot tub water was green and didn't get treated durung our 2 night stay. Driveway is long and narrow, but we managed it with a minivan.
Craig H. | Nov 2024
Perfect for our group of 6 - Three bedrooms and 3 Baths. Such a cute and comfortable little gem. Highly recommend
Mickie E. | Nov 2024
Perfect for 2 couples in key west if you are very close. 2 bathrooms made it perfect to get up, shower and get out there and have fun. A little tight for space, but if you plan on spending a lot of time in the unit, you are doing key west wrong! Would stay here again in a heartbeat.
Christopher R. | Nov 2024
Old Town Key West vacation rental FAQ

Yes, 29 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).

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Yes. 82 of our Old Town Key West vacation rentals have internet access, so you can stay connected throughout your trip.

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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.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons 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.

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   |   Duval Square - Key West   |   Key West   |   Florida
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