Rent Southold Homes with Swimming Pools

We selected the best homes worth renting in this location

Home spotlights

Like a Whisper

Like a Whisper

  • 11 guests

  • 7 bedrooms

Peconic, North Fork

This home has everything a group of friends or family need for a comfortable stay in Long Island's North Fork. The space is spread across three floors and although the decor is a little dated, there's lots to like.

Oyster Castle

Oyster Castle

  • 8 guests

  • 4 bedrooms

Westhampton Beach, Southampton

An eco-friendly haven away from the world, you can see that the host’s focus on sustainability was instrumental in this home’s design. A solar powered saltwater pool, solar panels on the roof, and an electric car charging port make this Hamptons home a green getaway that doesn't compromise on style.

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.

Dragonfly Creek

Dragonfly Creek

  • 6 guests

  • 3 bedrooms

Bridgehampton, Southampton

We love the rustic farmhouse feel of this home in the Hamptons, where whitewashed beams can be found in just about every room. The open-plan living area opens out onto a large wooden deck, where you can enjoy an alfresco meal with views over the surrounding wilderness.


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

Explore the 1 most perfect homes in our collection

View on map

Most popular homes

Poolside Splendour

Poolside Splendour

  • 8 guests

  • 4 bedrooms

East Quogue, Southampton

Hamptons Spring

Hamptons Spring

  • 12 guests

  • 6 bedrooms

Shinnecock Hills, Southampton

The Apple Picker's Perch

The Apple Picker's Perch

  • 16 guests

  • 8 bedrooms

North Sea, Southampton

Hampton Holiday

Hampton Holiday

  • 6 guests

  • 3 bedrooms

Hampton Bays, Southampton

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

The Little Sparrow

The Little Sparrow

  • 6 guests

  • 3 bedrooms

Shinnecock Hills, Southampton

Shinnecock Hills Seclusion

Shinnecock Hills Seclusion

  • 14 guests

  • 5 bedrooms

Shinnecock Hills, Southampton

View all


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

Search Our Collection