Rent Southampton Homes with Swimming Pools

We selected the 24 homes worth renting in this location

Home spotlights in Southampton

Blueberry Dream

Blueberry Dream

  • 6 guests

  • 4 bedrooms

Southampton, The Hamptons

Situated in Southhampton, only fifteen minutes from the storied Art Village on foot, this renovated home provides an idyllic base for families. Here, you're perfectly positioned for exploring, a six-minute drive from the soft white sands of Cryder and Cooper's Beach and even closer to Southhampton's bustling centre.

Long Island Bliss

Long Island Bliss

  • 6 guests

  • 3 bedrooms

Shinnecock Hills, Southampton

Located at the eastern edge of Southampton on Long Island's south shore, this modern townhouse is perfect for relaxing with family or friends after a day at the beach. Ideally positioned within 3-5 kilometres of Southampton’s boutique shops and restaurants – and less than a ten-minute walk to the ocean, it’s a great spot for a taste of seaside luxury.

Little Sailboat

Little Sailboat

  • 8 guests

  • 4 bedrooms

Southampton, The Hamptons

Forget the trend for bare walls and sterile interiors – this home looked minimalism in the face and said "I'm not about that". The floral sofas, rich rugs, antique wooden furniture and chandeliers create a maximalist design that avoids verging into the chintzy, instead offering a traditional Hamptons haven that any family can make themselves at home in.

The Portrait Painter

The Portrait Painter

  • 14 guests

  • 6 bedrooms

Southampton, The Hamptons

This charming Hamptons home is a great place for a family holiday or a large group of friends. The open floor plan, multiple living areas and formal dining room lend themselves perfectly to entertaining, while the fully-equipped kitchen, with a commercial-grade stove, is a chef's dream.


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

Explore the 24 most perfect homes in our collection

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Most popular homes in Southampton

The Little Sparrow

The Little Sparrow

  • 6 guests

  • 3 bedrooms

Shinnecock Hills, Southampton

Exist with the Sea

Exist with the Sea

  • 14 guests

  • 7 bedrooms

Southampton, The Hamptons

Alice in The Hamptons

Alice in The Hamptons

  • 8 guests

  • 5 bedrooms

Southampton, The Hamptons

Mary, Mary Quite Contrary

Mary, Mary Quite Contrary

  • 10 guests

  • 6 bedrooms

Southampton, The Hamptons

Seasons Of Love

Seasons Of Love

  • 6 guests

  • 5 bedrooms

Tuckahoe, Southampton

Hamptons Spring

Hamptons Spring

  • 12 guests

  • 6 bedrooms

Shinnecock Hills, Southampton

Shinnecock Hills Seclusion

Shinnecock Hills Seclusion

  • 14 guests

  • 5 bedrooms

Shinnecock Hills, Southampton

Somewhere In Time

Somewhere In Time

  • 8 guests

  • 4 bedrooms

Southampton, The Hamptons

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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 Southampton, The Hamptons, Suffolk County, New York, United States. 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 Southampton Home to Rent with a Swimming Pool today, and set up a holiday to remember.

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