Rent Luxury Accommodation in Shelter Island

We selected the 902 homes worth renting in this location

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Age 13+

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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.

Just A Minute

Just A Minute

  • 6 guests

  • 3 bedrooms

Water Mill, Southampton

Pack your bags and gather your favourite friends or family members, it's high time for a trip to the Hamptons. Just A Minute is a comfortable and modern home with easy access to Southhampton, where you can find everything you need from retail therapy to white sandy beaches.

The Mortar & Pestle

The Mortar & Pestle

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

The Mortar & Pestle takes its name quite literally from the mortar and pestle collection in the dining room, a detail that represents the character and charm of this home. The many indoor and outdoor social spaces cater to groups of friends and families who love home-cooked meals and value one another's company.

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

Nestled in the woodlands, this cabin provides cosy comfort and stylish charm. The outdoor area is the perfect place to keep toasty by the fire and eat delicious meals.


We selected the top 3% holiday homes in Shelter Island Accommodation

Explore the 902 most perfect homes in our collection

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Most popular homes in Shelter Island

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

Jewel on the Hudson

Jewel on the Hudson

  • 12 guests

  • 5 bedrooms

Coxsackie, New York

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

Swan's Nest

Swan's Nest

  • 7 guests

  • 4 bedrooms

Bridgehampton, Southampton

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

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Frequently asked questions

Take a look at our exclusive collection of luxury Accommodation in Shelter Island, and find your dream home. Each and every listing on our site has passed a vigorous testing process with flying colours, which is why we can be so certain that our collection is the best of the best. Only 3% of homes will ever make it onto Plum Guide, emphasising our incredibly high standards and making your job as easy as possible. Every home comes fully furnished with a perfectly-equipped kitchen, essential bathroom toiletries, and all linen included, so you will find everything you need. Get in contact with our friendly team of experts, whose sole purpose is to find you your ideal home, and book your stay in the finest Shelter Island Accommodation for Rent.

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