Shelter Island vacation rentals

4.96 out of 5 average rating, 171 reviews

A close-up view of a small plant is featured on a wooden surface, with soft natural lighting illuminating its leaves. The background is softly blurred, allowing the greenery to stand out, creating a calming and natural atmosphere.

Home in Southampton

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes

6-NIGHTS JULY 4TH WEEK-EXTRA 15% OFF NIGHTLY PRICING POST-QUOTE. Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

4.94 out of 5 average rating, 102 reviews

A private outdoor patio area is featured, displaying two lounge chairs and a small round table. Bright yellow flowering plants surround the space, complemented by a patterned area rug beneath the furniture. Cushions on the lounge chairs add subtle color to the setting.

Apartment in North Fork

Private 1st flr apt w/ patio 3 blocks from beach

We are centrally located in a quiet neighborhood within blocks from the heart of Greenport Village, Peconic Bay Beach, LIRR/Jitney, restaurants, shopping, Mitchell Park, and more! Explore local farms, wineries, breweries and all the North Fork has to offer. Beautifully furnished, ground floor apt with private entrance & patio area comfortably sleeps four, features a queen Tempur-Pedic mattress & convertible couch. Friendly, housetrained pets are welcome for an additional charge.

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.

4.89 out of 5 average rating, 27 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**

4.96 out of 5 average rating, 164 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

4.91 out of 5 average rating, 317 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!

A serene beach scene is depicted, showcasing soft white sand bordered by gentle waves. Tall grasses sway in the foreground, framing the clear blue water that extends to the horizon, providing a sense of calm and natural beauty.

4.92 out of 5 average rating, 100 reviews

Enjoy a relaxing getaway to the North Fork

One bedroom suite, with separate entrance in quiet Nassau Point; a peninsula, surrounded by beaches. Nassau Point is a great place to bike, walk and enjoy nature. Fully functioning WiFI for guests looking to extend their stay, while working from home. Fishermen's beach is a 5 minute walk Causeway beach is a 10 minute walk with parking. Point beach, 1.5 mile walk, a Southold Parking Permit required. You will find 20 wineries within 5 miles, just a short Uber ride away.

4.94 out of 5 average rating, 189 reviews

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).

A modern shower area features a glass enclosure with a textured tile wall. The stone floor is made of small pebbles, creating a natural feel. Fixtures are sleek and contemporary, including a handheld showerhead and a wall-mounted showerhead, situated next to a clean white toilet.

4.94 out of 5 average rating, 127 reviews

Comfortable Suite, a walk to the beach

Keep it simple at this spacious and peaceful home. Built in 2019, this home was specially designed for sustainable, green living; ground-source heating, and super insulation allow for minimal environmental impact. Less than five minute walk to McCabe’s Beach. Very near to wineries, farms, and the quaint shops and bakeries of Southold and Greenport. Little Fish restaurant and oyster sales all down the street. Short drive from Sparkling Pointe vineyard, and Love Lane.

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, 65 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!

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, 117 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$.

A vibrant seasonal market is displayed, featuring a yellow vintage truck parked in the foreground. Colorful chrysanthemums and pumpkins line the gravel pathway, while a rustic building adorned with decorative elements stands in the background against a cloudy sky.

4.88 out of 5 average rating, 668 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, 250 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

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Popular amenities for Shelter Island vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Shelter Island house rentals

A vibrant orange car is parked on a gravel driveway in front of a navy blue house. Lush greenery surrounds the property, and a neatly manicured lawn extends beside a stone walkway leading to the entrance.

4.99 out of 5 average rating, 97 reviews

Beach House in L.I. Wine Country

Superhost

The exterior of a modern cottage is presented with a black wood facade and multiple windows. A front porch is seen, partially enclosed with slatted wood. Lush green grass and shrubbery frame the entrance, creating a welcoming approach to the home.

4.88 out of 5 average rating, 34 reviews

Waterfront NoFo Cottage w/ public beach access

A vibrant flowering bush with large pink blooms is situated in the garden, adding color to the outdoor space. The wooden deck extends from the gazebo, and a rustic shed is visible in the background against a backdrop of green trees.

4.92 out of 5 average rating, 306 reviews

1830 Historic garden wing - walk to it all

The entrance of the home is framed by white, picket fencing and vibrant floral landscaping. A covered porch with classic columns supports a welcoming entrance. The door features decorative glass elements, providing an inviting touch to the exterior.

4.98 out of 5 average rating, 102 reviews

Designer's Dream - Charming Boathouse

A charming blue house is framed by lush green trees, with a welcoming front porch. Large windows invite natural light, while a white picket fence complements the tranquil outdoor setting. The spacious yard features vibrant grass, enhancing the peaceful atmosphere.

4.94 out of 5 average rating, 32 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

A spacious beach house is surrounded by lush greenery and vibrant flower beds. The structure features charming dark shingles and several windows that reflect natural light. Trees provide shade, enhancing the inviting outdoor space, which is set against a serene backdrop of Goose Creek.

5 out of 5 average rating, 12 reviews

Private Waterfront home with Dock!

5 out of 5 average rating, 17 reviews

The serene waterfront view captures the gentle hues of sunset reflected over the calm water. Lush greenery surrounds the area, and a wooden dock is visible, providing access to boats moored on the waterway. The sky displays a blend of soft pinks and purples.

Home in Sag Harbor

Sag Harbor Village Waterfront

4.86 out of 5 average rating, 36 reviews

An airy living space features high ceilings with skylights, allowing natural light to fill the room. A wooden dining table is surrounded by sleek chairs. A vibrant piece of artwork is mounted on the wall, and a large mirror reflects the inviting surroundings.

Home in Sag Harbor

Curated Artist Home with New Pool

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Other great vacation rentals in Shelter Island

A spacious bathroom features dual sinks set in a white marble countertop, accompanied by modern fixtures. Soft lighting is provided by wall sconces, while a large mirror enhances the bright atmosphere. A window allows natural light to enter, complementing the serene decor.

5 out of 5 average rating, 11 reviews

Waterfront Estate on Shelter Island. 100 Ft Dock

5 out of 5 average rating, 13 reviews

Waterfront Treehouse with Pool as seen on HBO

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, 11 reviews

Laid Back Relaxation

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

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, 6 reviews

Designer Renovated Farmhouse with Pool

A newly built house features a light-colored exterior with large, dark-framed windows. The entrance is highlighted by a small covered porch. Surrounding the home is a well-maintained lawn with neatly trimmed bushes lining the pathway, leading to a white gate on one side.