Vacation rentals in Shelter Island

An expansive outdoor area features a heated pool and hot tub, surrounded by lush greenery and tall trees. Lounge chairs with umbrellas are positioned nearby, set against a backdrop of vibrant grass and shaded by mature trees, creating a serene space for relaxation.

4.88 out of 5 average rating, 26 reviews

Newly Renovated w/ Pool, Hot tub & Fireplace

Shelter Island Rental License #: 2025-L-0056 !!!PLEASE DO NOT PUT IN A BOOKING REQUEST UNTIL WE HAVE HAD A CONVERSATION VIA THIS SITE. THANK YOU!!!! Great for fall and winter! Perfect for families! 4 Adults Max. Newly renovated, light filled home! Heated pool and hot tub in summer in a private tree-filled yard. Fireplace and great sledding in the colder months. Mid-century modern style; close to Shelter Island Heights and beaches. **POOL & HOT TUB CLOSED MID OCTOBER UNTIL MAY**

The living area features warm wood paneling and ample natural light from large windows. A wood-burning stove is positioned beside a comfortable sofa, with a chandelier offering soft illumination. A coffee table sits centrally, with various seating options and artwork on display.

4.96 out of 5 average rating, 163 reviews

Shelter island retreat

Two bedroom on the top floor of a house on Shelter Island on secluded one-acre. fire pit, wood-burning fireplace, layered decks, stainless steel kitchen, five minutes to beach. close to the south ferry .outdoor sauna and hot tub. Own entrance very private. owner lives on property as well in very separate space. 19W-0009 Own entrance very private. owner lives on premise as well in very separate space.has cat that lives in studio with owner 19W-0009 Long term rental also Available

Guest suite in North Fork

A modern bathroom features a walk-in shower with a glass enclosure and white subway tiles. A double vanity with sleek storage sits opposite a toilet. Decorative photos are arranged on the dark wall above the vanity, while a light fixture illuminates the space. A rug lies on the floor.

4.91 out of 5 average rating, 315 reviews

The Greenport Suite—private entry + near the beach

Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

4.93 out of 5 average rating, 121 reviews

A bathroom countertop showcases a washbasin alongside neatly stacked white towels. A decorative dish holds a bar of Dove soap, while a small bowl displays pink artificial flowers. A bottle of liquid soap and additional items are arranged in a stylish tray.

Apartment in Sag Harbor

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

4.94 out of 5 average rating, 186 reviews

A covered porch features two white wicker chairs positioned on a wooden deck. Natural light fills the space through nearby windows, enhancing the calm atmosphere. A glimpse of greenery and nearby structures can be seen in the surroundings.

Home in North Fork

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Guesthouse in Shelter Island

A serene saltwater pool is framed by lush greenery and blooming flowers, enhancing the outdoor space. A hot tub is positioned alongside, inviting relaxation. The guest house is visible in the background, surrounded by trees and well-maintained landscaping.

5 out of 5 average rating, 64 reviews

Bayfront 1BR/2BR detached guesthouse with pool

Perfect relaxing getaway for a couple or family. Bayfront 1BR/2BR fully detached guest house with gorgeous morning views. Property has saltwater pool + hot tub (open May -October) and bay access via private dock. Central to both north & south forks (wineries + Hamptons or Montauk just short drive away). Down the road from famous Shelter Island Sunset Beach + golf course. Come explore the beauty of the Hamptons without the stress!

5 out of 5 average rating, 26 reviews

Hamptons - Shelter Island Farmhouse

Kid friendly! Perfect two family split! Come enjoy our island retreat. Relax with the whole family at this peaceful pad. You will be 2 min on bike from Wades Beach. You can also walk to the best BBQ/seafood in Shelter, Commander Codys. Features a large open kitchen/dining room plus also a spacious living room. 4 bedrooms with new mattresses, huge outdoor patio for family BBQs. No dogs please.

Superhost

A fire pit is positioned on the sandy beach, with flames flickering brightly. The setting sun casts warm hues of orange and pink across the horizon, reflecting off the calm water, creating a serene atmosphere for evening gatherings.

4.9 out of 5 average rating, 116 reviews

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Home in Shelter Island Heights

4.95 out of 5 average rating, 39 reviews

Silver Beach, 3 Bedroom cottage w/ pool

Enjoy summer on Shelter Island in this 3 bedroom, 2 bathroom, freshly painted and well equipped MCM ranch house on 3/4 of an acre. Located at the end of a private road, it's in walking distance to Shell Beach, town landings and a beautiful sunset viewing spot. Brand new, heated, inground pool w/ color changing light, central air, deck, fire pit and BBQ make this a great vacation home.

Guest suite in North Fork

A sandy path lined with tall grass leads to a serene beach. The gentle waves of the ocean can be seen in the distance under a clear blue sky, inviting a peaceful atmosphere.

4.88 out of 5 average rating, 665 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Apartment in Shelter Island Heights

A round wooden dining table is surrounded by four metal chairs. Natural light enters through two large windows, with framed black-and-white photographs arranged on the wall beside them. A decorative centerpiece is placed on the table, offering a rustic touch to the space.

4.91 out of 5 average rating, 247 reviews

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone

A serene poolside scene features a clear blue saltwater pool alongside a comfortable lounge area. An umbrella provides shade over the sunbed, while a rustic outdoor seating arrangement sits nearby, surrounded by lush trees and well-maintained landscaping.

5 out of 5 average rating, 63 reviews

CASA GYPSEA - a chic and peaceful 3 bedroom house

Unwind and quiet your mind in the spacious yard surrounded with lovely specimen trees. Take a dip in the salt water gunite pool and enjoy never-ending afternoon lunch in the outdoor salon. This is a lovingly remodeled house, beautifully furnished, with many collection books and a full french library.

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Popular amenities for Shelter Island vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Shelter Island

4.89 out of 5 average rating, 9 reviews

Serenity on Shelter Island with a Pool & Hot tub

ChrisRating, 5 stars9 months ago

Mary Ann was a great host. Super responsive and provide excellent details and very helpful information. Her house is beautiful with a wonderful oasis in the back with pool, hot tub, and fire pit with plenty of space to lounge. Our family felt right at home and very comfortable. We hope to come back again.

Home in Shelter Island Heights

An outdoor mahogany deck features a circular dining table surrounded by four wicker chairs, with additional seating in the form of a loveseat. Two large umbrellas provide shade, and a gas grill is covered and positioned nearby. Lush greenery is visible in the background.

5 out of 5 average rating, 10 reviews

Laid Back Relaxation

SallieRating, 5 stars2 weeks ago

We really enjoyed Jared’s property. The light-filled living and dining room were spacious and comfortable, and the kitchen was modern and well-equipped. We would stay here again!

A serene waterfront scene captures gentle waves lapping against smooth rocks. The sky displays a captivating sunset with hues of orange, pink, and purple reflecting on the water's surface, creating a peaceful atmosphere at the day's end.

4.93 out of 5 average rating, 80 reviews

Family Friendly Island Home

LelandRating, 5 stars9 months ago

Bruno’s place was really quaint and nice. Bruno was easy to communicate with. Would recommend it again for sure!

A modern cabin is seen with black wooden siding and large glass doors. Soft lighting fixtures are mounted on either side, illuminating the entrance. Surrounding greenery includes potted plants and a bush, with a rustic dining area visible nearby.

5 out of 5 average rating, 5 reviews

Designer Renovated Farmhouse with Pool

FrancisRating, 5 stars1 month ago

We really needed the solitude and my daughter and I had a fantastic rest. What a great place to hibernate in the winter! Great comfortable beds, well stocked kitchen In a beautiful space. It is a bird sanctuary with nice walks and brilliant cycling.

A spacious estate is set against a twilight sky, with two separate dwellings visible amid well-manicured lawns. Large trees provide shade, while warm light glows from the windows, indicating a welcoming atmosphere. The serene surroundings emphasize the property's privacy and seclusion.

5 out of 5 average rating, 6 reviews

6-acre Hidden Estate for 10 w/FP, Pool, Chef's Kit

JaneRating, 5 stars1 week ago

Several of my family members stayed at Christine's house while on Shelter Island for a family wedding. The main house and cottage were both so beautiful and so comfortable and cozy. The grounds were positiviely idyllic including the tucked away, inviting pool. It truly felt like it could be our family's house. We all fell in love. The beds were comfortable with crisp white linens. When we weren't outside, the kitchen was a constant gathering place as was the sunroom and the dining room. I can't say anything about the TVs since we didn't turn one on once. Didn't even think about it - were having too much fun being together. Internet was great! Before arrival, Christian was a constant source of communication, making sure we were all set. Pay attention to his succinct instructions of how to get to the house. They are spot on. Kim, the manager, was there to greet us and let us in and answer any questions. She was so helpful. Going to SI? Stay at Christine's! You'll be glad you did!

Guesthouse in Shelter Island

A spacious outdoor seating area with a low, sectional sofa and a circular coffee table is set on a wooden dock. Two large umbrellas provide shade over the seating area, while the surrounding greenery reflects in the calm water of Menantic Creek.

4.89 out of 5 average rating, 9 reviews

Stylish Studio Suite on Shelter Island

AnnaRating, 5 stars10 months ago

Kate’s place was perfect—down a quiet and private road but close to everything Shelter Island has to offer. The apartment was cozy and comfortable with all the necessities. Kate was very responsive when needed but you also have privacy. Lovely stay—I hope to come again!

A bright dining area is complemented by large windows offering views of the waterfront. A wooden table is positioned near the windows, with a light-colored chair nearby. A stylish blue cabinet with various bottles and glassware is visible, contributing to the inviting atmosphere.