A man carrying a woman in front of a pool with two American flags, surrounded by greenery and a monument.

Photo by Brittany Schreiber

Town of Southampton holiday rentals

We found 3,708 holiday rentals — enter your dates for availability

Select from 1674 houses, 46 apartments and other holiday rentals to find the perfect place for your stay in Town of Southampton. Whether you’re staying in a holiday home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a hot tub. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Popular Town of Southampton destinations on Stayz

A beach with a wooden fence, a lifeguard tower, and a house with a balcony overlooking the ocean.

Southampton

A beach with waves, a clear sky, and two people walking.

Hampton Bays

A pebbled beach at sunset with the sun setting over the horizon.

Riverhead

A marina with several boats docked, including a white motorboat and a sailboat with a canopy.

Sag Harbor

A coastal landscape with green marshland and a distant shoreline.

Westhampton Beach

A lake surrounded by residential properties, a tennis court, and a large house with a swimming pool.

Bridgehampton

Holiday rentals with weekly discounts – Town of Southampton

Showing deals for:13 Nov - 20 Nov

Exceptional

(10 reviews)

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Orient

8% off

AU$16,963

for 7 nights, 1 room

AU$2,423 per night

includes taxes & fees

Dining table and picnic table
water view

Heated pool with gorgeous water and natural wetland view

Chef kitchen with breakfast area on 2nd floor

Exceptional

(35 reviews)

Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!

Southampton

8% off

AU$12,312

for 7 nights, 1 home

AU$1,759 per night

includes taxes & fees

Exceptional

(15 reviews)

Beautiful Hamptons Family Escape.

Westhampton

8% off

AU$9,976

for 7 nights, 1 home

AU$1,425 per night

includes taxes & fees

view from living room towards pool, outdoor dining

Exceptional

(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off

AU$81,791

for 7 nights, 1 home

AU$11,684 per night

includes taxes & fees

Exceptional

(6 reviews)

Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway

Hampton Bays

8% off

AU$14,360

for 7 nights, 1 home

AU$2,051 per night

includes taxes & fees

Exceptional

(97 reviews)

Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town

Sag Harbor

16% off

AU$11,893

for 7 nights, 1 home

AU$1,699 per night

includes taxes & fees

Exceptional

(5 reviews)

Shirley Bayfront Getaway – Kayak, Swim & Relax

Shirley

8% off

AU$8,510

for 7 nights, 1 home

AU$1,216 per night

includes taxes & fees

An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining +10,)

Exceptional

(26 reviews)

Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

Southampton

30% off

AU$14,356

for 7 nights, 1 home

AU$2,051 per night

includes taxes & fees

Exceptional

(8 reviews)

Stunning fall sunsets, coveted location on Mecox Bay - recently furnished

Water Mill

8% off

AU$55,052

for 7 nights, 1 home

AU$7,865 per night

includes taxes & fees

Exceptional

(10 reviews)

Southampton Village Charmer - South of Highway

Southampton

8% off

AU$30,699

for 7 nights, 1 home

AU$4,386 per night

includes taxes & fees

Exceptional

(60 reviews)

Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool

Southampton

8% off

AU$19,866

for 7 nights, 1 home

AU$2,838 per night

includes taxes & fees

Exceptional

(29 reviews)

“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath

Mastic Beach

9% off

AU$4,386

for 7 nights, 1 home

AU$627 per night

includes taxes & fees

Resort inspired backyard with heated pool, outdoor seating, and complete privacy

Exceptional

(16 reviews)

NEW DECK! Private 1 Acre Family Friendly Home - Heated Pool, Home Office & Gym

Westhampton

8% off

AU$9,121

for 7 nights, 1 home

AU$1,303 per night

includes taxes & fees

Stairs to the upstairs living room, kitchen and dining room

Exceptional

(27 reviews)

Modern Family Retreat with Heated Pool, Playground and Peloton

Hampton Bays

8% off

AU$11,474

for 7 nights, 1 home

AU$1,639 per night

includes taxes & fees

Exceptional

(10 reviews)

Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL

Sag Harbor

8% off

AU$20,633

for 7 nights, 1 cottage

AU$2,948 per night

includes taxes & fees

Exceptional

(44 reviews)

Westhampton Beach Town and Country

Westhampton Beach

8% off

AU$11,297

for 7 nights, 1 home

AU$1,614 per night

includes taxes & fees

Very good

(34 reviews)

Waterfront Home With Recreational Dock! Great For Rafting, And Close To Beaches

Mastic Beach

8% off

AU$3,644

for 7 nights, 1 home

AU$521 per night

includes taxes & fees

Wonderful

(20 reviews)

2-Acre Modern Estate in Southampton. Beach, winery, farm, pool, and hot tub

Riverhead

8% off

AU$6,060

for 7 nights, 1 home

AU$866 per night

includes taxes & fees

Exceptional

(33 reviews)

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Riverhead

8% off

AU$7,468

for 7 nights, 1 home

AU$1,067 per night

includes taxes & fees

Spacious living room with sliders to the patio pool and backyard

Kitchen is stocked with a selection of pots dishes and utensils

Enjoy nearby North Fork and South Fork wineries and many other local attractions

This area is perfect for reading and relaxing

Exceptional

(107 reviews)

Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach

Westhampton Beach

8% off

AU$6,879

for 7 nights, 1 home

AU$983 per night

includes taxes & fees

Exceptional

(21 reviews)

Beautiful Private Studio Apartment!

Ridge

7% off

AU$1,626

for 7 nights, 1 apartment

AU$232 per night

includes taxes & fees

Exceptional

(28 reviews)

9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub

Sag Harbor

8% off

AU$20,530

for 7 nights, 1 home

AU$2,933 per night

includes taxes & fees

Hydrangeas blooming all summer.these are the August bloomers

Featured as one of most beautiful poolsides

Kitchen walks out to covered porch across length of entire back

Living area on 1st floor with wood burning fireplace

Exceptional

(7 reviews)

IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES

Southampton

8% off

AU$25,781

for 7 nights, 1 home

AU$3,683 per night

includes taxes & fees

Exceptional

(15 reviews)

Charming Riverhead home with large outdoor patio & backyard firepit

Riverhead

12% off

AU$4,268

for 7 nights, 1 home

AU$610 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find the best place to stay - Town of Southampton

North Fork Resort

Sleeps 4 · 1 bedroom

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

Sleeps 12 · 5 bedrooms · 5 bathrooms

Nice Hampton Bays ,4 Queen Bdr, CAC, Billiard, Bbq, dis

Sleeps 8 · 4 bedrooms · 2 bathrooms

Stunning Beach House steps to ocean beach

Sleeps 8 · 3 bedrooms · 2 bathrooms

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

Sleeps 14 · 6 bedrooms · 4 bathrooms

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

Sleeps 16 · 7 bedrooms · 4 bathrooms

Find the perfect holiday rental for your Town of Southampton getaway

Learn about the unique charm of Town of Southampton with a stay in a holiday home rental. 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 attractions to visit during your stay? Venture out of your cosy holiday rental and check out everything that Town of Southampton has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

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)
Paumanok Vineyards (7.8 mi / 12.6 km)
Macari Vineyards (8.8 mi / 14.1 km)
Martha Clara Vineyards (9.1 mi / 14.7 km)

Exploring the natural features in Town of Southampton

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Town of Southampton is a great place to get outside. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city centre:

Meschutt Beach (1.6 mi / 2.5 km)
Shinnecock East County Park (2.3 mi / 3.7 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)

Transport 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 centre.

If you're travelling by train, Hampton Bays Station, Southampton Station and Westhampton Station are the main stations that serve the city.

Frequently asked questions

What is the best area to stay in Town of Southampton when booking a holiday home?

Snap up a holiday home in Village of Southampton and experience one of Town of Southampton's most renowned areas. Coopers Beach and Southampton Historical Museum are two major attractions here that'll keep you occupied during your visit.

What is the most popular type of holiday home accommodation in Town of Southampton?

The most desirable types of holiday homes in Town of Southampton are houses. Searching for something different? Stayz has a variety of options to match the unique needs of our guests, so you'll see properties in loads of shapes and sizes. The ideal fit is ready and waiting for you — grab yours today.

How much does it cost to rent a holiday home in Town of Southampton?

The average price for a holiday home in Town of Southampton is based on a number of factors, such as time of year, length of stay and property type. Whether you're in search of a sprawling villa with a pool or a quaint cottage for you and your other half, just add your travel dates to discover stays that offer great value.

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

The average price for a holiday home near the beach in Town of Southampton depends on when you're visiting the area and the size and type of property you're searching for. You can easily find prices on Stayz by entering your dates of travel. Then use our filters to select the number of bedrooms and amenities important to you, like WiFi, air conditioning and a pool.

Are there pet-friendly holiday homes in Town of Southampton?

Pack a travel bag and a bone for your pup because Town of Southampton has 1 ,537 properties that put out the welcome mat to pets. Let your four-legged friend get in on the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your destination and dates, then check our "Pets allowed" filter box.

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

Add a whole other level of fun to your getaway by booking one of the 1 ,125 houses with a private pool in Town of Southampton. Use our search filter to find properties with pools on Stayz, then spend carefree days frolicking in a swimming pool that's exclusively for you.

What are popular home amenities in Town of Southampton?

When it comes to home amenities that people are on the lookout for in Town of Southampton, a swimming pool, a sauna and a nearby waterfront are the most popular. With Stayz holiday homes, you'll discover options to match your style and taste, whether you're going on a trip with friends, family or even pets.

Are there large group holiday homes in Town of Southampton?

Choose from 449 holiday homes in Town of Southampton that can accommodate a group of 10 or more guests. Whether you're organising a family holiday or some kind of special event, there's ample space to get your favourite people together under one roof.

Are there holiday homes in Town of Southampton that welcome kids?

Gather your whole crew for an adventure in Town of Southampton at one of our 1 ,534 family-friendly properties. Many of these stays offer amenities that are ideal for getaways with children, such as full kitchens, extra bedrooms and pools. Simply check the "Properties good for families" filter and book your favourite.

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

There's a ton of fabulous things to see and do with the family in Town of Southampton, such as:

Coopers Beach
The Hamptons Beaches
Long Island Aquarium and Exhibition Centre

Are there one-bedroom holiday homes in Town of Southampton?

Yes, you'll find 79 one-bedroom properties in Town of Southampton to pick from. A one-bedroom holiday property is a wonderful choice if it's just the two of you or if you're holidaying alone. Throw in more convenience, space and privacy than a standard hotel, and you're sure to have a trip to remember.

Can I find two-bedroom holiday homes in Town of Southampton?

Take off with your loved ones and enjoy peace, privacy and comfort in one of the 112 two-bedroom holiday homes Town of Southampton has to offer.

Are there holiday homes with WiFi in Town of Southampton?

Whether you want to keep up with the headlines, look over emails or post a pic to social media, there are 555 holiday homes with WiFi in Town of Southampton. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.

How can I find holiday homes with air conditioning in Town of Southampton?

Choose from 1 ,484 holiday homes with air conditioning in Town of Southampton providing that cool, cool breeze and extra touch of comfort. Just enter your preferred dates of travel and then use our filter tool to help you book properties with air conditioning.

How old do you have to be to rent a holiday home in Town of Southampton?

The minimum age can vary across properties on Stayz, so check the rules of the holiday home in Town of Southampton you're interested in. But usually, it's 16, 18 or 21.

How long can I rent a holiday home in Town of Southampton for?

The length of time you can rent a holiday home in Town of Southampton varies according to the property. Simply enter your preferred dates to view a list of options offering extended stays. With tons of creature comforts such as air conditioning and laundries, as well as some offering weekly or monthly discounts, you're sure to discover someplace just right to call your home away from home in Town of Southampton.

More holiday ideas

Holiday homes