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We selected the 806 homes worth renting in this location

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Home spotlights in Southampton

Painted Shadows

Painted Shadows

  • 6 guests

  • 3 bedrooms

Loudonville, Colonie

This charming home is listed on the National Register of Historic Places, so character comes as standard here. Furnished with antique pieces and an eclectic art collection, it’s a house that’s packed with personality – from the cosy lounge and gourmet kitchen (ideal for entertaining and evenings in), to the chic bedrooms and bathrooms (complete with refined roll-top tubs).

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Not too far from the bright lights of New York City, this striking and stylish home sits near the beaches of Westhampton and among the protected marshlands of Long Island. The house itself is a modern twist on the traditional clapboard homes the area is famous for, with wraparound decks looking into the treetops to the rear and plenty of sliding doors allowing the indoors to seamlessly slip into the outdoor space.

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Sea Aster sits in an ideal spot for exploring beach and town life. Sag Harbor Main Street, with its restaurants, boutiques and artisan bakeries, is less than fifteen minutes’ walk away, and you can get to Haven’s Beach – a perfect spot to watch the sun set – in ten.

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Dating back to the eighteenth century, it’s safe to say that The Whaler’s Cottage is steeped in history. It has a wonderful garden with lots of room for relaxing, and the interiors are stunning.


We selected the top 3% holiday homes in Southampton Family Friendly Rentals

Explore the 806 most perfect homes in our collection

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Most popular homes in Southampton

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, New York

The Rainbow Bird

The Rainbow Bird

  • 8 guests

  • 4 bedrooms

Woodbury, Litchfield County

Marble Muse

Marble Muse

  • 8 guests

  • 4 bedrooms

Water Mill, Southampton

Far Away Coast

Far Away Coast

  • 8 guests

  • 5 bedrooms

North Sea, Southampton

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

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Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Southampton, The Hamptons, Suffolk County, New York, United States. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent Southampton Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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