Rent Amagansett Homes with Swimming Pools

We selected the 104 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

An extra fee may apply

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Home spotlights in Amagansett

Sweet Cicely

Sweet Cicely

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Set in 15 acres of private grounds, this modern mountain chalet in New York’s Catskills is the ultimate Upstate getaway. Inside, the place is rustic yet refined with timber vaulted ceilings, mid-century modern furnishings and a creamy colour palette.

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Escape the frenetic pace of daily life and revel in an unmissable opportunity to relax and recharge at this stunning Shelter Island getaway. Set on a quiet tree-lined street and just a ten-minute walk from the pebble-strewn seashore, the home is perfectly set up for family holidays and weekend retreats with friends.

The Little Sparrow

The Little Sparrow

  • 6 guests

  • 3 bedrooms

Shinnecock Hills, Southampton

Radiating coastal luxury, this towering home with its streamlined kitchen, natural lighting and picture-perfect minimalist rooms stands on an acre of land in the affluent Hamptons. Location-wise, you're surrounded by art museums and trendy mom-and-pop shops, with the historic Shinnecock Hills Golf Club under five minutes away by car and Meschutt Beach not much further.

Tucked In The Trees

Tucked In The Trees

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Get set to escape reality and embrace all things lavish and luxurious as you retreat to this sensational, mid–century East Hampton's home. Newly renovated and sat on 1.


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

Explore the 104 most perfect homes in our collection

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Most popular homes in Amagansett

Hamptons Dreams

Hamptons Dreams

  • 9 guests

  • 3 bedrooms

East Hampton North, East Hampton

Just A Minute

Just A Minute

  • 6 guests

  • 3 bedrooms

Water Mill, Southampton

When In Bloom

When In Bloom

  • 6 guests

  • 3 bedrooms

Southampton, The Hamptons

Tudoresque

Tudoresque

  • 10 guests

  • 5 bedrooms

Ossining, Westchester County

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

Want For Nothing

Want For Nothing

  • 11 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

The Mortar & Pestle

The Mortar & Pestle

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Walcott

Walcott

  • 8 guests

  • 3 bedrooms

Bridgehampton, Southampton

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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 Amagansett. 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 Amagansett Home to Rent with a Swimming Pool today, and set up a holiday to remember.

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