Discover a selection of 3,000 vacation rentals in Town of Southold Town that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $193 per night, and houses and condos are popular options for a stay in Town of Southold Town. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Town of Southold Town
Destination guide

Southold Town: family memories are made here

Southold Town lies along the furthermost tip of Long Island, around 100 miles east of New York City. It's long been a getaway destination for families from the Big Apple and while it may not have the glitz and glam of the nearby Hamptons, it's got a wealth of things to do nonetheless. It doesn't matter if you're a beach bum, foodie or adventure nut, you'll find everything you need near your Southold Town vacation rental. Top that with some family-friendly attractions, some quaint town festivities and a few wineries, and you've just found your new summer hotspot.

Things to do

Star gazing in Southold

There are several points of interest near your Southold Town vacation rental that warrant time away from your beach towel. Don't know your Orion from your Big Dipper? At the Custer Institute and Observatory, Long Island's oldest observatory, you can take in the starry night sky and learn about the constellations. Alternatively, take a visit to the Horton Point Lighthouse, which has been keeping passing ships safe since the mid-19th century, or learn about the native Indians which once inhabited Long Island and view an impressive collection of arrowheads and other artifacts from those days.


Sail the Long Island coast from Southold Town

Southold Town is where family adventures are made. If you've brought the kids, they'll love the water-based activities, which range from sea kayaking to sailing. Alternatively, you can dive into a fishing store for bait and try your hand at reeling in supper to take back to your Southold vacation rental. Coastal hiking is always popular, as is cycling along the country lanes. There are seasonal activities too. In late summer, you can swing by one of the local fruit or vegetable farms with the little ones, to get them picking their own produce.


Highly changeable weather in Southold Town

Your stay in a Southold Town can be drastically different depending on the time of year that you visit. During summertime, families escape stuffy New York City and head 100 miles east to Long Island for time by the sea. It's certainly the hottest time to visit but also the most crowded. While the shoulder seasons might be a little cooler, that's the only sacrifice you'll have to make in return for a quieter vacation and a dip in rental prices. Winter sees Southold deserted by travelers, but the dramatic weather can be wonderful in your cozy Southold Town vacation rental.

Natural features

Spot ospreys in Southold Town

Nestled along miles of shoreline on nearby Shelter Island, the Mashomack Preserve has one of the densest wildlife populations in the north-east. The preserve has been part of the Nature Conservancy since 1980 and takes up more than 2,000 acres and more than a 1/3 of the island. Its forest, marshland and tidal creeks provide habitats for many birds, but the highlight is sightings of nesting ospreys, one of the largest populations along the East Coast, along with piping plovers and terns. The calm salt marshes also serve as an important breeding ground for young marine life.

How many vacation rentals are available around Town of Southold Town?

Our 2021 property listings offer a large selection of 3,130 vacation rentals around Town of Southold Town. From 2,907 house rentals to 119 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Town of Southold Town?

Yes, of course. Vrbo has 2,907 Houses in Town of Southold Town. Our other popular types of vacation rentals in Town of Southold Town include:

  • Condos/Apartments: 119 rentals available
  • Studios: 82 rentals available
  • Cottages: 256 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Farmhouses and more.

Can I find a vacation rental with pool in Town of Southold Town?

Yes, you can select your preferred vacation rental with pool among our 1,605 vacation rentals with pool available in Town of Southold Town. Please use our search bar to access the selection of vacation rentals available.