Luxury houses For rent Shelter Island, United-States

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56 listings
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32
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House Shelter Island (United-States)

2025 Rates: June $30,000, July $60,000, July-August $125,000 and August-Labor Day $65,000. This stunning two-story home sits on 3.44 acres of beautiful lawns and trees, featuring a circular driveway and a double-arched covered porch with bluestone patio.... Read more

$ 30,000 IC / month
  • 5 bedrooms
  • 6 bathrooms
  • land 1.4 ha

By Daniel Gale Sotheby's International Realty

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Listings near Shelter Island

20
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House East Marion (United-States)

Not available for year round rent at this time. Newly renovated three bedroom, two bath bungalow just outside of popular Greenport Village.This house provides a sense of privacy and relaxation close to the beach. Located less than one mile away, the... Read more

$ 4,600 IC / month
  • 3 bedrooms
  • 2 bathrooms
  • land 1 012 m2

By Daniel Gale Sotheby's International Realty

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18
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House East Marion (United-States)

Relax and enjoy this beautifully appointed bay front house w/ private beach and stunning views of Orient Harbor, Bug Light and Shelter Island. Moor your boat in the bay; kayak, swim, fish or chill on the decks and porches. Basement game room w/... Read more

$ 12,000 IC / month
  • 4 bedrooms
  • 4 bathrooms
  • land 1 578 m2

By Daniel Gale Sotheby's International Realty

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25
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House with garden Sag Harbor (United-States)

Also available Nov 1 - Apr 30 $36K This beautiful waterfront home in Sag Harbor is now available for rent for the first time. Sweeping views of the Little Narrows section of Sag Harbor abound and are afforded from many areas of the property. Highlights... Read more

$ 33,000 IC / month
  • 3 bedrooms
  • 3 bathrooms
  • land 3 035 m2

By Sotheby's International Realty - Bridgehampton Brokerage

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9
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Property Orient (United-States)

Magical 1840's Cottage in Browns Hills with endless views across Orient Bay. Beautiful south facing garden abutting farm fields. Three bedrooms 1.5 baths, outdoor shower, deeded sound beach. A private, tranquil natural sanctuary in bucolic Orient.... Read more

$ 15,000 IC / month
  • 3 bedrooms
  • 2 bathrooms
  • land 2 388 m2

By Daniel Gale Sotheby's International Realty

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14
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House Orient (United-States)

Enjoy a beautiful airy and bright mint condition Bay Front Orient Contemporary home, perfect for relaxing and entertaining. This 4-bedroom 4.5 bath home has gourmet kitchen, fireplace, open common space for easy entertaining. First floor has access to... Read more

$ 10,000 IC / month
  • 4 bedrooms
  • 5 bathrooms
  • land 1 942 m2

By Daniel Gale Sotheby's International Realty

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15
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House Orient (United-States)

Experience breathtaking views of Long Island Sound and Orient Point County Park from this spacious open-concept home. This beautifully updated 4-bedroom, 4-bathroom residence offers a private 20x40 heated saltwater in-ground pool and serene backyard.... Read more

$ 20,000 IC / month
  • 4 bedrooms
  • 4 bathrooms
  • land 3 885 m2

By Daniel Gale Sotheby's International Realty

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28
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House Orient (United-States)

Amazing North Fork home with heated salt water gunite pool located in Grandview Estates featuring 4 bedrooms (1st floor bedroom with ensuite, 2 ensuite guest bedroom on the second floor with 1 additional guest bedroom and guest bathroom) office/den also... Read more

$ 110,000 IC / month
  • 4 bedrooms
  • 5 bathrooms
  • land 4 452 m2

By Daniel Gale Sotheby's International Realty

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17
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House Orient (United-States)

Impeccably restored 19th Century gem located in the heart of Orient Village with bay views. Close to bay and sound beaches, and a stroll to all village amenities. Featuring 2 parlors, 3 bedrooms, library, office, eat-in kitchen, updated baths, charming... Read more

$ 10,000 IC / month
  • 3 bedrooms
  • 2 bathrooms
  • land 1 335 m2

By Daniel Gale Sotheby's International Realty

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10
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House Greenport (United-States)

Situated in a charming and serene neighborhood in Greenport and located just minutes from both Greenport Village and Southold Town Beach, this recently updated Cape offers 1,500 sq. ft. with 4-bedrooms, 2-baths and a spacious living area that flows... Read more

$ 3,800 IC / month
  • 4 bedrooms
  • 2 bathrooms

By Daniel Gale Sotheby's International Realty

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23
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House Greenport (United-States)

Classic contemporary style New Construction in the heart of Greenport Village. This 2900+ sqft offering features 4 wide white oak hardwood floors throughout w/ inviting Great Room, eat-in Kitchen and Junior Suite bedroom on Main Level. The second floor... Read more

$ 3,950 IC / month
  • 4 bedrooms
  • 4 bathrooms
  • land 607 m2

By Daniel Gale Sotheby's International Realty

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30
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Farm house Greenport (United-States)

Summer 2024 Rates: May24-June30 $20K, July2-Aug1 $30K, Aug2-Sept3 $35K, Sept4-Oct4 $15K: Rare new construction on a quiet side street in Greenport Village, this modern luxury home is the perfect base to explore the beaches, wineries, and farm-to-table... Read more

$ 13,500 IC / month
  • 5 bedrooms
  • 4 bathrooms
  • land 526 m2

By Daniel Gale Sotheby's International Realty

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24
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House with pool East Hampton (United-States)

Here's the perfect home for year-round living or summer enjoyment! Sited on a beautifully landscaped 1+/- acre in the Northwest Woods that's convenient to East Hampton Village and bay beaches, this lovely property boasts 4 bedrooms, 2.5 baths, and much... Read more

$ 25,000 IC / month
  • 4 bedrooms
  • 3 bathrooms
  • land 4 047 m2

By Sotheby's International Realty - East Hampton Brokerage

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28
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House East Hampton (United-States)

Welcome to your dream retreat! This distinctive older home boasts five thoughtfully designed levels, offering an abundance of space and character. Each floor presents a unique ambiance, perfect for both relaxation and entertaining. Key Features: ... Read more

$ 85,000 IC / month
  • 3 bedrooms
  • 2 bathrooms
  • land 1 619 m2

By Daniel Gale Sotheby's International Realty

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11
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House East Hampton (United-States)

Welcome to your new sanctuary! This beautifully designed split-level home offers 4 spacious bedrooms and 3 modern bathrooms, perfect for families or those seeking extra space. As you enter, a few steps past the kitchen you'll be greeted by a bright and... Read more

$ 50,000 IC / month
  • 4 bedrooms
  • 3 bathrooms
  • land 1 457 m2

By Daniel Gale Sotheby's International Realty

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23
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House with pool East Hampton (United-States)

Newly renovated 1900's classic full of period charm in prime East Hampton Village location, short distance to Main Street and Jitney. Living room with fireplace, formal dining room, dream entertaining kitchen, sunroom and new screened porch overlooking... Read more

$ 45,000 IC / month
  • 4 bedrooms
  • 4 bathrooms

By Sotheby's International Realty - Bridgehampton Brokerage

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11
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House East Hampton (United-States)

This 3 Bedroom, 2 bathroom, modern home is the perfect centrally located Hamptons getaway! A private home nestled into a quiet and friendly neighborhood in close proximity to bay beaches, a few marinas, great hiking trails, and amazing waterfront... Read more

$ 55,000 IC / month
  • 4 bedrooms
  • 3 bathrooms
  • land 1 457 m2

By Daniel Gale Sotheby's International Realty

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14
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House East Hampton (United-States)

A welcoming first floor with beautiful natural light from the giant sliders welcoming you to the deck with a large and heated pool. Enjoy the privacy protected by lush green trees and bring relaxation to the next level. Upstairs you will find two good... Read more

$ 25,000 IC / month
  • 3 bedrooms
  • 2 bathrooms
  • land 2 347 m2

By Daniel Gale Sotheby's International Realty

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10
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House East Hampton (United-States)

This just renovated ranch centrally located in Springs offers and incredible stay to its guests. An outdoor shower to cool down from the beach just down the road, a large lawn space for hanging in the evening, and a wonderful deck with a grill to bbq.... Read more

$ 40,000 IC / month
  • 2 bedrooms
  • 2 bathrooms
  • land 2 792 m2

By Daniel Gale Sotheby's International Realty

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36
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Farm house Southold (United-States)

2025 Rates: July $32,500, July-August $67,500 and August-Labor Day $35,000. Brand New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out... Read more

$ 32,500 IC / month
  • 4 bedrooms
  • 4 bathrooms
  • land 1 862 m2

By Daniel Gale Sotheby's International Realty

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