Old Town Key West Vacation Rentals

Compare 62 vacation rentals.
1 Guest
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, apartments, and more

housing_type_house.jpg

House rentals

View 22 House rentals
housing_type_condo.jpg

Condo rentals

View 19 Condo rentals
housing_type_apartment.jpg

Apartments

View 5 Apartments

Popular amenities for Old Town Key West vacation rentals

Popular
Dog-friendly Hot tub Internet
Old Town Garden Villas - Andros Suite
1 Bedroom | 1.5 Bath | Sleeps 4

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

$280 avg / night
(excludes fees and taxes)
4.75 (138)
Old Town Garden Villas - Abaco Suite
1 Bedroom | 1.5 Bath | Sleeps 4

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

$431 avg / night
(excludes fees and taxes)
4.69 (123)
Key Lime Calypso
2 Bedroom | 1 Bath | Sleeps 6

Key Lime Calypso - Key West, FL

$791 avg / night
(excludes fees and taxes)
4.54 (110)
Tradewinds
4 Bedroom | 2 Bath | Sleeps 12

Tradewinds - Key West, FL

$949 avg / night
(excludes fees and taxes)
4.44 (59)
Leeward Isle
2 Bedroom | 1 Bath | Sleeps 6

Leeward Isle - Key West, FL

$210 avg / night
(excludes fees and taxes)
4.51 (74)

View 57 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

Clean, well provisioned vacation condo in the heart of everything!
Ney L. | Jul 2025
This place was everything we expected. Perfect layout and great location right off Duval Street. Good parking and easy access. Place was clean and we had everything we needed for our stay.
Craig F. | Jul 2025
Walk to everything. Had a great stay in this cute key west cottage. Beds were very comfortable and needed after a long day of fun. Would stay here again.
Trista P. | Jul 2025
Old Town Key West vacation rental FAQ

Yes, 21 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. 62 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
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
Show more  
Su
Mo
Tu
We
Th
Fr
Sa
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2