Rent Connecticut Homes with Swimming Pools

We selected the 95 homes worth renting in this location

Home spotlights in Connecticut

The Fifties Barn

The Fifties Barn

  • 8 guests

  • 4 bedrooms

East Hampton, The Hamptons

Once a 1950s potato barn, this historic home now provides rustic charm in the affluent Hamptons. Though we fell in love with the loft library, dramatic furnishings, and leafy garden, complete with a private pool and hot tub, the location is also worth mentioning.

All American

All American

  • 10 guests

  • 5 bedrooms

Shelter Island Heights, Shelter Island

That all-American, wood clad, cosily furnished Hamptons home you've been dreaming of? We've found it.

Lunar Glow

Lunar Glow

  • 8 guests

  • 4 bedrooms

North Sea, Southampton

For those in search of a classic Hamptons getaway, this home ticks all the right boxes. Southampton is just a fifteen-minute drive away and there’s easy access to beautiful beaches.

Port & Starboard

Port & Starboard

  • 6 guests

  • 6 bedrooms

North Haven, Southampton

This European-inspired villa ticks all the boxes for an indulgent stay while feeling close to nature. Tucked into woodland and surrounded by manicured lawns, it features a stepping-stone path leading to a private beach and boat so you can set sail on the gentle waters of Noyack Bay.


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

Explore the 95 most perfect homes in our collection

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Most popular homes in Connecticut

Artistic Sensibility

Artistic Sensibility

  • 8 guests

  • 3 bedrooms

East Hampton North, East Hampton

An Old Fashioned

An Old Fashioned

  • 8 guests

  • 4 bedrooms

Napeague, East Hampton

Sing Blue

Sing Blue

  • 8 guests

  • 4 bedrooms

Amagansett, East Hampton

Make it Yours

Make it Yours

  • 8 guests

  • 4 bedrooms

East Hampton North, East Hampton

Coral Skies

Coral Skies

  • 6 guests

  • 3 bedrooms

Montauk, East Hampton

Like a Whisper

Like a Whisper

  • 11 guests

  • 7 bedrooms

Peconic, North Fork

East Hampton Breeze

East Hampton Breeze

  • 4 guests

  • 3 bedrooms

Springs, East Hampton

Solstice Rise

Solstice Rise

  • 8 guests

  • 6 bedrooms

Amagansett, East Hampton

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

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