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We selected the 910 luxury monthly villas and homes worth renting in this location

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Home spotlights in Shelter Island

The Striped Sea Bass

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.

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Look out for artists, poets and musicians in the area around this home – it’s located in Springs, arguably the coolest town in the Hamptons. In the past, it’s played host to visionaries like Jackson Pollock and Lee Krasner, Willem de Kooning, Kurt Vonnegut, and John Steinbeck.

Jewel on the Hudson

Jewel on the Hudson

  • 12 guests

  • 5 bedrooms

Coxsackie, New York

This riverfront home is the kind of getaway we dream of every day. The infinity pool and views of the Hudson River are magnificent – just imagine how calming it is to wake up to views of this calibre every day.

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

There are some homes that simply capture your heart from the moment you arrive. And we won’t be surprised if it’s love at first sight when you see this charming Colonial saltbox house.


We selected the top 3% holiday homes in Shelter Island Monthly Rentals

Explore the 910 most perfect homes in our collection

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Most popular homes in Shelter Island

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

Just A Minute

Just A Minute

  • 6 guests

  • 3 bedrooms

Water Mill, Southampton

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Dappled Sunlight

Dappled Sunlight

  • 8 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Painted Shadows

Painted Shadows

  • 6 guests

  • 3 bedrooms

Loudonville, Colonie

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, North Fork

Villa Menantic

Villa Menantic

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Shelter Island, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Shelter Island Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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