Book Luxury Monthly Rentals in Shelter Island

We selected the 920 homes worth renting in this location

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Home spotlights in Shelter Island

Whale Watching

Whale Watching

  • 8 guests

  • 4 bedrooms

Sag Harbor, Southampton

Arriving at this effortlessly chic seaside home from the city is a shockingly swift affair – you can be in Manhattan for breakfast and Sag Harbour for lunch. With its white-washed interiors and beachy accents, the home is ideal for a family of weekenders or those looking for a long-term change of scenery.

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.

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.

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

There are a lot of adjectives we could throw at this home in The Berkshires; cosy, darling, divine. But none of them really do it justice.


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

Explore the 920 most perfect homes in our collection

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Most popular homes in Shelter Island

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Sweet Cicely

Sweet Cicely

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Kennedies

Kennedies

  • 9 guests

  • 4 bedrooms

North Sea, Southampton

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

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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