Book Luxury Monthly Rentals in Shelter Island

We selected the 900 homes worth renting in this location

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Home spotlights in Shelter Island

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.

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 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, Nora Ephron and John Steinbeck.

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Built in 1800, Hitchbrook is a quintessential New England home. Surrounded by farmland and rolling hills, this home is a private getaway for those looking for a pastoral retreat.

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 Monthly Rentals

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Most popular homes in Shelter Island

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

On the Edge of Nature

On the Edge of Nature

  • 4 guests

  • 3 bedrooms

Gardiner, New York

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

Jewel on the Hudson

Jewel on the Hudson

  • 12 guests

  • 5 bedrooms

Coxsackie, New York

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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