Southampton which includes street scenes

Town of Southampton vacation rentals

We found 3,731 vacation rentals — enter your dates for availability

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Select from 1597 houses, 26 condos, and other vacation rentals to find the perfect place for your stay in Town of Southampton. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll have the amenities you expect and more, which might include a pool and a washer and dryer. Whatever you're looking for, you'll be able to choose a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Town of Southampton

Showing deals for:Aug 1 - Aug 8

Exceptional

(6 reviews)

Chic Modern Private Designer 1.5 Acre Private Oasis

East Hampton, NY

35% off

Exceptional

(6 reviews)

4 House from Beach 4-Bd Retreat 3 bath, w/ Pool, Hot Tub, & TESLA Charger

East Hampton, NY

7% off

Beautiful home w/ 18x36 ft heated pool, 2 sundecks, & spacious, private grounds

Exceptional

(7 reviews)

Bright, light home w/ modern kitchen, 4-5 minute drive to East Hampton Village!

East Hampton, NY

15% off

Expansive back yard with large deck, heated pool, putting green, chipping areas.

Exceptional

(12 reviews)

Get out of city. Luxury Family Retreat; Pool, Putting Green, great outdoor deck

Westhampton, NY

10% off

Exceptional

(12 reviews)

East Hampton updated, large 3BR/3BA cottage on private beach on a 2-acre lot.

East Hampton, NY

5% off

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Town of Southampton

Ocean,pool, boardwalk bay, bed,new kitch,new bath,new furn, steps to ocean

Sleeps 16 · 7 bedrooms · 4 bathrooms

Luxury Home W/ Huge Rap Around deck largest Pool on ocean private large dining

Sleeps 13 · 6 bedrooms · 4 bathrooms

Designer Oceanfront Luxury Bdrms! surround sound art collection,hot tubonBeach

Sleeps 12 · 5 bedrooms · 5 bathrooms

Summer 2025 Early Booking Special July or August 35K - Sag Harbor Gem

Sleeps 12 · 4 bedrooms · 2 bathrooms

Top rated rentals - Town of Southampton

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Find the perfect vacation rental for your Town of Southampton getaway

Learn about the unique charm of Town of Southampton with a stay in a private vacation home. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Town of Southampton

Are you looking for top things to see and do during your stay? Venture out of your cozy vacation rental and check out everything that makes Town of Southampton a fun spot to vacation. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

Shinnecock Hills Golf Course (3.1 mi / 5 km)
Duck Walk Vineyards (6.9 mi / 11 km)
Jamesport Vineyards (7.6 mi / 12.2 km)
Macari Vineyards (8.8 mi / 14.1 km)
Peconic Bay Winery (10.1 mi / 16.2 km)
Bedell Cellars (10.8 mi / 17.4 km)

Exploring the natural features in Town of Southampton

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Town of Southampton is a great place to get outside. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

Meschutt Beach (1.6 mi / 2.5 km)
Ponquogue Beach (2.6 mi / 4.2 km)
Tiana Beach (2.8 mi / 4.5 km)
Sandbar Beach (4.1 mi / 6.5 km)
Cooper's Beach (4.5 mi / 7.3 km)
The Hamptons Beaches (10.5 mi / 17 km)

Transportation to and around Town of Southampton

Fly into Westhampton, NY (FOK-Francis S. Gabreski), the closest airport, located 8.1 mi (13 km) from the city center.

If you're traveling by train, Hampton Bays Station, Southampton Station and Westhampton Station are the main stations in the area.

Frequently asked questions

What is the best area to stay in Town of Southampton when booking a vacation rental?

One of the most sought-after neighborhoods to book a vacation rental in Town of Southampton is Bay Point. Find the perfect stay on Vrbo and experience this area like a local.

What is the most popular type of vacation rental accommodation in Town of Southampton?

The most in-demand types of vacation rentals in Town of Southampton are cottages. Looking for something different? Vrbo has plenty of options to match the diverse needs of our guests, so you’ll see properties in all shapes and sizes, and for all budgets. The perfect fit is waiting for you — get yours today.

How much does it cost to rent a vacation rental in Town of Southampton?

A number of things can influence what you’ll pay for a vacation rental in Town of Southampton, such as the time of year, property type and length of stay. Still, all Vrbo homes have something in common — exceptional value. Just enter your travel dates to find your home away from home.

How much does it cost to rent a beach house in Town of Southampton?

The average price for a vacation rental by the beach in Town of Southampton depends on when you’re going and the style and size of property you want. Find prices easily and quickly on Vrbo by entering your travel dates. Then use the handy filters to select the number of bedrooms and amenities that you prefer, like air conditioning, WiFi and a hot tub.

Are there pet-friendly vacation rentals in Town of Southampton?

You’re in luck! There are. You can pick from 1,754 vacation rentals that allow pets in Town of Southampton. Many of our pet-friendly vacation rentals even have an outdoor space for your fur baby to run around in, special dog beds, complimentary treats and proximity to parks. Apply the “Pets allowed” filter to find a vacation home on Vrbo that’s pawfect.

Can I rent a house with a pool in Town of Southampton?

Add an extra layer of fun to your trip by booking your crew into one of the 1,237 houses with a private pool in Town of Southampton. Use our handy search filter to find the kind of property you want on Vrbo, and then spend leisurely days splashing and playing in a swimming pool that’s exclusively for you.

What are popular rental amenities in Town of Southampton?

When it comes to rental amenities that guests are on the lookout for in Town of Southampton, a beach view, a chef and a nearby waterfront are at the top of the list. With Vrbo vacation rentals, there are options to suit your style and taste, whether you’re going on a trip with your partner, your family or even pets.

Are there large group vacation rentals in Town of Southampton?

With 539 vacation rentals that can host 10 guests or more in Town of Southampton, there’s no need to leave anyone off your invite list. From fun family vacations to events like Thanksgiving or Christmas parties, Vrbo will help you find a large group rental that fits the occasion.

Are there vacation rentals in Town of Southampton that welcome kids?

Bring the entire family together for an adventure in Town of Southampton at one of our 1,705 family-friendly vacation rentals. Lots of these stays offer amenities that are just perfect for trips with the kids, such as full kitchens, multiple bedrooms and patios. Just click on the “Properties good for families” filter box and pick out your favorite.

What are the top attractions for families in Town of Southampton?

There are plenty of exciting things to see and do with the family in Town of Southampton, such as:

Meschutt Beach
Westhampton Beach Performing Arts Center
Hallockville Museum Farm

Are there one-bedroom vacation rentals in Town of Southampton?

Yes, there are 90 one-bedroom properties in Town of Southampton to pick from. A one-bedroom vacation home is a wonderful choice if it’s just two of you or if you’re traveling alone. Add in more space, privacy and convenience than a regular hotel, and you’re sure to have a break to remember.

Can I find two-bedroom vacation rentals in Town of Southampton?

You can pick from 131 two-bedroom homes in Town of Southampton. Give the kids the second room or maybe fill it with a couple of your nearest and dearest friends. There’s space for whoever’s lucky enough to come along for the ride.

Are there vacation rentals with WiFi in Town of Southampton?

Town of Southampton has 667 vacation rentals with WiFi, so you can stay connected while you’re on vacation. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming movies with your family to writing and sending emails, these Vrbo homes make it a cinch to get online.

How can I find vacation rentals with air conditioning in Town of Southampton?

Choose from 1,686 Vrbo vacation rentals with air conditioning in Town of Southampton giving you that gentle, cool breeze and extra element of comfort. Just enter your preferred travel dates and then use our handy filters to help you locate stays with air conditioning.

How old do you have to be to rent a vacation rental in Town of Southampton?

The minimum age is usually 16, 18 or 21. It can vary across properties on Vrbo, so check the rules of your chosen Town of Southampton stay before booking.

How long can I rent a vacation rental in Town of Southampton for?

The amount of time you can rent a Town of Southampton vacation rental for is down to each property. Just tap in your dates of travel to browse options offering longer term stays. They include all you require to make your extended break more enjoyable and convenient, like air conditioning and laundries. Some Vrbo vacation homes may also offer discounted weekly or monthly prices, so you can stay even longer for less.

Does Vrbo offer discounts for vacation homes in Town of Southampton?

Weekend break or extended escape, Vrbo has some great deals and discounted options in Town of Southampton that’ll suit your style and budget. Browse our weekly and monthly discounts on vacation rentals, or check out what’s recently been added with one of our newly listed homes. Whatever it is you’re after, you’ll find the perfect place to stay — without breaking the bank.