Rent The Hamptons Homes with Swimming Pools

We selected the 58 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights in The Hamptons

The Mortar & Pestle

The Mortar & Pestle

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

The Mortar & Pestle takes its name quite literally from the mortar and pestle collection in the dining room, a detail that represents the character and charm of this home. The many indoor and outdoor social spaces cater to groups of friends and families who love home-cooked meals and value one another's company.

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

Once an 1890s carriage house, this home has been designed for country living for a small family. Low timber ceilings and hardwood floors retain the barn-like element, but instead of hay bales, you’ve got comfortable king-size beds for grown-ups and secret sleeping spots for kids in the mezzanine above the loft.

Run to the Sea

Run to the Sea

  • 6 guests

  • 3 bedrooms

Montauk, East Hampton

At the eastern end of Long Island, 120 miles from New York and surrounded by more than 5,000 acres of parkland and beaches, there's little not to love about this warm and peaceful Montauk retreat. To fully enjoy everything this home is about, take some deep breaths, shut off your phone and quiet your mind in the serenity of the meditation room, tucked away just off the second bedroom.

Hamptons Dreams

Hamptons Dreams

  • 9 guests

  • 3 bedrooms

East Hampton North, East Hampton

Exploring East Hampton is a breeze at this coastal cottage. Both downtown and the beach are easily accessible by bike, and a coffee shop and seafood restaurant are just down the street.


We selected the top 3% holiday homes in The Hamptons Homes with Swimming Pools

Explore the 58 most perfect homes in our collection

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Most popular homes in The Hamptons

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

Marble Muse

Marble Muse

  • 8 guests

  • 4 bedrooms

Water Mill, Southampton

Zephyr Residence

Zephyr Residence

  • 10 guests

  • 5 bedrooms

Water Mill, Southampton

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, Southold

Want For Nothing

Want For Nothing

  • 11 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

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Check upcoming rates & availability for The Hamptons Homes with Swimming Pools


Frequently asked questions

You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in The Hamptons. Our exclusive collection consists solely of homes that have passed our thorough 150-step vetting process with flying colours, so you can book with true peace of mind, knowing that everything from decibel levels in the bedroom to a room's intangible atmosphere has been tested and approved. We don't list a huge number of homes one our site, just the right ones. Each property in our collection comes fully furnished and ready to welcome you, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Contact our dedicated team of experts to find the perfect luxury The Hamptons Home to Rent with a Swimming Pool today, and set up a holiday to remember.

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