Discover a selection of 2,000 vacation rentals in The Village of Southampton 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 kitchens. Prices start at $650 per night, and houses and cottages are popular options for a stay in The Village of Southampton. Either way, you'll find a rental for everyone's needs.
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.


See Southampton in style

Thanks to its superb coastal location, Southampton has tons of great activities. Charter a luxury yacht for your group or family and explore the coast of Long Island in style. There’s a whole range of trips on offer, from exploring the oceanfront homes to cruising around the beautiful islands. For Southampton vacation rentals that are perfect for some ‘me time,’ check out properties near the luxurious spas for some chilled pampering, or near the many golf courses, where you can work on your swing. If you’re looking to get the adrenaline pumping, look toward the sea for the wide variety of watersports.


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

How to get to and around Southampton

The nearest airport is in East Hampton, NY (HTO), located 9.4 mi (15.1 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Westhampton, NY (FOK-Francis S. Gabreski), which is 12.7 mi (20.5 km) away.

If you'd prefer to travel by train, you can make your way to Southampton Station.

How many vacation rentals are available around The Village of Southampton?

Our 2020 property listings offer a large selection of 2,002 vacation rentals around The Village of Southampton. From 1,771 house rentals to 111 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to The Village of Southampton?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in The Village of Southampton:

  • East Hampton North: 297 vacation rentals
  • Clearwater Beach: 96 vacation rentals
  • Remsenburg: 45 vacation rentals
  • Silver Beach: 45 vacation rentals
  • Amagansett Lanes: 63 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

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

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

  • Cooper's Beach: 2,730 vacation rentals
  • Halsey House: 2,742 vacation rentals
  • Southampton Station: 2,751 vacation rentals
  • Shinnecock Hills Golf Course: 1,882 vacation rentals
  • Southampton Cultural Center: 2,739 vacation rentals

But there are many other points of interest around The Village of 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 The Village of Southampton?

Yes, of course. Vrbo has 1,771 Houses in The Village of Southampton. Our other popular types of vacation rentals in The Village of Southampton include:

  • Cottages: 111 rentals available
  • Condos/Apartments: 34 rentals available
  • Bungalows: 111 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 The Village of Southampton?

Yes, you can select your preferred vacation rental with pool among our 1,355 vacation rentals with pool available in The Village of Southampton. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around The Village of Southampton

    East Hampton
    2,451 vacation rentals
    Sag Harbor
    2,287 vacation rentals
    Hampton Bays
    1,873 vacation rentals
    Westhampton Beach
    765 vacation rentals
    1,815 vacation rentals
    East Quogue
    872 vacation rentals
    Water Mill
    1,804 vacation rentals
    1,476 vacation rentals
    672 vacation rentals
    Shelter Island
    2,008 vacation rentals
    972 vacation rentals
    543 vacation rentals
    853 vacation rentals
    513 vacation rentals
    738 vacation rentals
    785 vacation rentals
    2,458 vacation rentals
    East Marion
    326 vacation rentals
    268 vacation rentals
    390 vacation rentals