Discover a selection of 2,000 vacation rentals in Southampton, NY 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 private pools. Prices start at $775 per night, and houses and condos are popular options for a stay in Southampton. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Southampton
Destination guide

Picturesque beauty and extravagance in Southampton

Southampton is often associated with luxury and old money, and that’s certainly true when booking Southampton vacation rentals. The properties here are stunning, and most feature a pool, should you ever tire of the breathtaking beaches and wish to enjoy a dip in privacy. A place that has long attracted writers and artists, it has plenty of cultural attractions to explore, such as the Shinnecock Nation Cultural Center and Museum. Then top it all off with a quaint town center, packed with great restaurants and quirky specialty shops, and you’ve got one unbeatable vacation destination.

Things to do

Step back in time in Southampton

When you’re not sunning yourself on the beach, head to the town of Southampton where there are some great family-friendly attractions for you to enjoy. Be sure to visit the Southampton Historical Museum, which gives a superb insight into the history of the area. Comprising 12 buildings, including a blacksmith’s shop and a carpentry shop, the highlight is the beautifully restored 19th-century mansion house. Set in another historic building, the Southampton Arts Center provides fantastic exhibitions and events, covering everything from sculptures to live jazz. They also offer many kid-friendly events, making it ideal for families.


Take full advantage of summer in Southampton

To get the full benefit of Southampton’s incredible beaches, it’s best to plan to visit during the summer months. From June through August, temperatures hover between the high 60s to high 70s; perfect for a refreshing and relaxing dip in the sea and for kicking back on the beach. Spring and fall are also solid choices, when the temperatures are that little bit milder. But if you find the water too cold, don’t worry, there are hundreds of Southampton vacation rentals that come with their own pool.

Natural features

Explore the breathtaking coast of Southampton

The picturesque, unspoiled beaches are just one of the many beautiful attractions when it comes to the landscape of Southampton. One of the best ways to experience the rich wildlife of the area is by taking a trip to Conscience Point Historic Site and Nature Walk. It’s open all year round, and as you walk through its gentle trails, you’ll be rewarded with beautiful panoramas across Peconic Bay. Around 60 acres of maritime grasslands and rugged, windswept dunes play host to a wide variety of flora and wildlife, including many species of birds like osprey and the American black duck.

How to get there

Transportation to and around Southampton

Fly into MacArthur Airport (ISP), the closest airport, located 37.6 mi (60.5 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to East Hampton, NY (HTO), which is 9.1 mi (14.7 km) away.

If you'd rather travel by train, the main station is Southampton Station.

How many vacation rentals are available around Southampton, NY?

Our 2022 property listings offer a large selection of 1,826 vacation rentals around Southampton. From 1,708 house rentals to 44 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Southampton?

Vrbo offers a large selection of vacation rentals near lovely places in Southampton. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Southampton Cultural Center: 2,963 vacation rentals
  • Southampton Arts Center: 2,975 vacation rentals
  • Halsey House: 2,966 vacation rentals
  • Shinnecock East County Park: 2,548 vacation rentals
  • National Golf Club: 2,975 vacation rentals

But there are many other points of interest around Southampton listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Southampton?

Yes, of course. Vrbo has 1,708 Houses in Southampton. Our other popular types of vacation rentals in Southampton include:

  • Condos/Apartments: 44 rentals available
  • Cottages: 88 rentals available
  • Bungalows: 88 rentals available

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

Can I find a vacation rental with pool in Southampton?

Yes, you can select your preferred vacation rental with pool among our 1,267 vacation rentals with pool available in Southampton. Please use our search bar to access the selection of vacation rentals available.