Beachfront Rentals in Shelter Island

Curated beachfront vacation rentals

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Adults

Age 13+

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Age 1 to 12

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Home spotlights in Shelter Island

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

If you’re in search of a coastal adventure or a relaxing beachfront escape, this home delivers the perfect solution. Nestled in Stonington village, you’ll be spoiled by beautiful views, an expansive two acres of lush grounds, a private pool and a tennis court.

Blissful Thinking

Blissful Thinking

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

Experience the Hamptons in all of its heyday glory with a stay at Blissful Thinking. The former homestead and summer camp embodies one of the last wild spaces in the Hamptons, nestled right by the water's edge and facing Gardiner's Island.

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, Southold

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 Shelter Island Beachfront Rentals

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Frequently asked questions

Planning your next summer holiday? You’ve come to the right place: Plum Guide offers a handpicked collection of the best beach houses and beachfront cottages in Shelter Island. Whether you're dreaming of waking up to the sound of waves crashing on the shore or enjoying a sunset dinner on your private deck overlooking the sea, our carefully curated homes are perfect for your ideal beach getaway. From charming beachfront cottages to luxurious seaside villas, each property is fully furnished with the best-equipped kitchens and all linen included, ensuring you feel right at home. Dive into the ultimate beach experience with Plum Guide’s exceptional collection of vacation rentals in Shelter Island.

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