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Rent Connecticut Homes with Swimming Pools

We selected the 68 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Connecticut

Dappled Sunlight

Dappled Sunlight

  • 8 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Make like a New Yorker and escape to the famous Hamptons. This home has everything you could need for an effortless, laidback break from the city.

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.

The Archway

The Archway

  • 9 guests

  • 4 bedrooms

West Hurley, Hurley

Urbanites looking for a tranquil getaway will enjoy the large indoor and outdoor spaces to relax and unwind. Each room has been lovingly styled by the host, Ayanna, who has instilled her character and charm into the home.

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, North Fork

Anyone with a subscription to HBO might recognise The Old Life-Saving Station. The home has featured in both Lena Dunham’s Girls, and more recently, The Undoing, starring Hugh Grant and Nicole Kidman.

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

Explore the 68 most perfect homes in our collection

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Most popular homes in Connecticut

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Want For Nothing

Want For Nothing

  • 11 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

Doric Detail

Doric Detail

  • 8 guests

  • 4 bedrooms

Dover, Dutchess County

Upstate Escape

Upstate Escape

  • 10 guests

  • 4 bedrooms

Woodstock, Ulster County

Hudson Grandeur

Hudson Grandeur

  • 16 guests

  • 8 bedrooms

Cornwall, Orange County

Technicolour Dreamland

Technicolour Dreamland

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Hamptons Dreams

Hamptons Dreams

  • 9 guests

  • 3 bedrooms

East Hampton North, East Hampton

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

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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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