Southold Vacation Rentals

Compare 5 vacation rentals.
USA > New York > Southold

Make Southold your next getaway

Staying at a Southold, New York, vacation rental surrounds you in this charming community's historic excellence and natural coastal beauty. Here, you'll find a delightfully picturesque town enveloped by scenic beaches, recreation, vineyards, and museums. You're going to love it here. 

Explore Southold house rentals, and more

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House rentals

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Popular amenities for Southold vacation rentals

Popular
Dog-friendly Hot tub Internet
Classic Southold Country Charmer
2 Bedroom | 1 Bath | Sleeps 4

Classic Southold Country Charmer - Southold, NY

$165 avg / night
5.0 (2)
Secret Garden Estate
4 Bedroom | 4 Bath | Sleeps 10

Secret Garden Estate - Southold, NY

$1,012 avg / night
Minnehaha Marvel
1 Bedroom | 2 Bath | Sleeps 4

Minnehaha Marvel - Southold, NY

$202 avg / night
3.0 (1)
Southold Serenity
3 Bedroom | 2.5 Bath | Sleeps 8

Southold Serenity - Southold, NY

$437 avg / night
3.0 (1)
Watersedge Retreat
3 Bedroom | 2 Bath | Sleeps 6

Watersedge Retreat - Southold, NY

$513 avg / night

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Recent Southold guest reviews

Everything went very, the staff were very helpful with anything I needed help with.
Donald B. | Aug 2024
Perfect location, close to state parks and beautiful nature. Very well equipped kitchen- high quality cookware and dishes. Cozy, warm - but need to clean the kitchen carpet
Norman & Jozica G. | Oct 2021
Southold vacation rental FAQ

Yes, 15 of our Southold 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. 27 of our Southold 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 Southold 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 Southold 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 Southold, 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

Where do I find the best vacation rentals for families in Southold, NY? 

We offer a series of family-friendly vacation rentals in Southold. This includes homes with enough space and bedrooms to house larger get-togethers as well as smaller cottages for more intimate travel. 

We recommend reviewing your Southold vacation rental options to find the perfect lodging for your next family trip. 

What is Southold, NY, known for?

Southold is known for its rich history, with several historical landmarks and museums to explore, such as the Southold Historical Society Museum and the Custer Institute and Observatory, the oldest public observatory in the United States.

In terms of its economy, Southold is primarily driven by tourism, agriculture, and fishing. The town is home to several vineyards, wineries, local farmers' markets, and seafood restaurants that serve fresh seafood from the nearby waters.

Overall, Southold is a charming and peaceful town that offers a relaxed and laid-back lifestyle with plenty of opportunities to enjoy the area's natural beauty and local culture.

Explore our Southold, NY, vacation rentals

From pet-friendly accommodations to vacation rentals for families in Southold, we offer some of the best places to stay in the area. Ready to plan your next vacation to this unique New York community? We thought so. Get inspired by exploring your rental options in Southold.