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.
Rent Shelter Island Homes with Swimming Pools
We selected the 106 homes worth renting in this location
Home spotlights in Shelter Island
Hamptons Dreams
9 guests
3 bedrooms
East Hampton North, East Hampton
Exploring East Hampton is a breeze at this coastal cottage. Both downtown and the beach are easily accessible by bike, and a coffee shop and seafood restaurant are just down the street.
Marble Muse
8 guests
4 bedrooms
Water Mill, Southampton
It may look Old World from the outside, but behind this home's traditional shingle exterior is a luxurious and playful home to call your own in The Hamptons. Packed with designer touches, we love the bright, double-height living space, with its character fireplace and huge windows.
The Striped Sea Bass
6 guests
3 bedrooms
Bay Point, Noyack
If you’re looking for all the charm of a country cottage with the space and grandeur of a manor house, this is the spot for you. It’s a four-minute stroll to the vast stretch of sand at Long Beach and a six-minute drive sees you in the heart of the pretty village of Sag Harbor.
We selected the top 3% holiday homes in Shelter Island Homes with Swimming Pools
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You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in Shelter Island. 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 Shelter Island Home to Rent with a Swimming Pool today, and set up a holiday to remember.
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