Rent Connecticut Homes with Swimming Pools

We selected the 74 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Connecticut

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.

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.

When In Bloom

When In Bloom

  • 6 guests

  • 3 bedrooms

Southampton, The Hamptons

This Hamptons house sits on seven acres of lush greenery, with plenty of space for both kids and adults to enjoy. Old meets new inside, with patterned rugs, antique furniture and an imposing fireplace, along with a slick kitchen complete with coffee grinder and juicer.

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

A luxurious harbour-front villa overlooking the serene Noyack Bay, this home's stylish interior boasts elegance and sophistication. Huge, panoramic windows display the beautiful surroundings while flooding the space with light.


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

Explore the 74 most perfect homes in our collection

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Most popular homes in Connecticut

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Walcott

Walcott

  • 8 guests

  • 3 bedrooms

Bridgehampton, Southampton

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Upstate Escape

Upstate Escape

  • 10 guests

  • 4 bedrooms

Woodstock, Ulster County

Just A Minute

Just A Minute

  • 6 guests

  • 3 bedrooms

Water Mill, Southampton

Hamptons Dreams

Hamptons Dreams

  • 9 guests

  • 3 bedrooms

East Hampton North, East Hampton

Light of Romance

Light of Romance

  • 14 guests

  • 6 bedrooms

Springs, East Hampton

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

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

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