Book Luxury Monthly Rentals in Shelter Island

We selected the 936 homes worth renting in this location

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Home spotlights in Shelter Island

Magic in The Hamptons

Magic in The Hamptons

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

This beautiful home is set within dense woodland on the northern East Hampton Coast, just two blocks from a private beach looking out over Gardiners Bay. Inside, there are beautiful hardwood floors, a cosy fireplace for cool evenings and cathedral-like ceilings over the dining area.

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

At the bottom of the garden, you’ve got direct access to the serene waters of Noyack Bay, with kayaks, paddleboards and bicycles provided by your host. It’s a fifteen to twenty-minute walk (or five-minute cycle) to the restaurants and grocery store of Noyack, just along the coast from Sag Harbour.

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Live your best East Hampton life at this light-filled, mid-century architectural gem, just a seven-minute drive from the beach. With its private pool and hot tub, grassy lawns backed by juniper trees for post-pool games (table tennis, anyone?

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

Explore the 936 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

Just A Minute

Just A Minute

  • 6 guests

  • 3 bedrooms

Water Mill, Southampton

Whale Watching

Whale Watching

  • 8 guests

  • 4 bedrooms

Sag Harbor, Southampton

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

When In Bloom

When In Bloom

  • 6 guests

  • 3 bedrooms

Southampton, The Hamptons

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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