Family-friendly holiday rentals in Shelter Island

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Shelter Island

  • Total holiday rentals

    Explore 110 holiday rentals in Shelter Island

  • Nightly prices starting at

    Shelter Island holiday rentals start at $255 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,270 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Shelter Island holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Shelter Island rentals

  • 4.9 Average rating

    Shelter Island stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Shelter Island

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
Home in Springs

Serene + private ~ 1 block to waterfront dining

Enjoy zen living at this serene, chic, Hamptons oasis! Ideally located 1 block to waterfront dining, 8 minutes to beaches + 9 minutes to Main St! Relax poolside w/ tons of greenery + nature views. Spark up the BBQ + firepit under the starry sky. Listen to the crickets + spot a deer on the property. Curl up to the wood burning fireplace, cook in your Chef's kitchen + stream on your 80' TV Enjoy coffee on the sea + dinner w the best sunsets just 1 block away. A perfect escape + place to unwind!

4.91 out of 5 average rating, 141 reviews
Top Guest favourite
An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.
Home in Bridgehampton

Amazing Home close to Everything -

Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grounds are smoke-free.

4.94 out of 5 average rating, 334 reviews
Top Guest favourite
A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.
Home in Mattituck

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

4.93 out of 5 average rating, 134 reviews
Guest favourite
Home in Sag Harbor

Barefoot Bliss | Quiet Family Retreat Heated Pool

Welcome to your Hamptons retreat. This bright single-level home sits in a quiet neighborhood just minutes from Main Street and the ocean. The private fenced yard overlooks a peaceful nature preserve and features a heated pool (June–Sept, heating available for a fee), hot tub, outdoor fireplace, and outdoor shower—perfect after a beach day. Family-friendly amenities include a sandbox, toys, crib, and highchair, with a separate safety fence surrounding the pool for added peace of mind.

4.91 out of 5 average rating, 202 reviews
Top Guest favourite
A cozy living area is shown with two comfortable sofas and a coffee table. Natural light enters through two windows adorned with bamboo shades. A flat-screen television is mounted on the wall, and a decorative rug adds warmth to the wooden flooring.
Apartment in Sag Harbor

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

4.98 out of 5 average rating, 241 reviews
Superhost
A bright living area features large windows that offer views of the nearby pond. Comfortable seating includes a white sofa, patterned chairs, and a coffee table, all arranged on a natural fiber rug. Light from the windows enhances the serene atmosphere.
Home in Sag Harbor

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds, 2.5 baths - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond -Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action. NOTE: Due to water leakage issues, the bath in pool house is not available

4.86 out of 5 average rating, 138 reviews
Guest favourite
Home in Shelter Island Heights

Hay Beach Family Home: Fire Pit, Playroom, Yard

Two blocks from Hay Beach, this family-and-dog-friendly 3BR sleeps 6 in a quiet Shelter Island neighborhood. Fenced yard, fire pit, playroom, crib, toddler toys, beach gear, and bikes included. The home was built for families: open living area with wood-burning fireplace, full kitchen, 2 full baths, basement playroom, and workout space. Outside: fully fenced yard, fire pit, sun loungers, propane grill, Big Green Egg. Winter stays: $0 cleaning fee Nov–Mar.

4.9 out of 5 average rating, 129 reviews
Top Guest favourite
A cozy living area is highlighted by a chandelier, providing soft illumination. Two stylish chairs flank a round table, while a decorative sculpture and a vintage fireplace enhance the space. Large windows allow natural light to fill the room, offering views of the surrounding greenery.
Home in Sag Harbor

The Cooper-Burke House

Many Main Street restaurants such as the American Hotel, Lulu's, Page 63, Wolffer Kitchen, Sen, Sag Pizza and Goldberg's, etc are a few minutes away. On Main Street one finds the Sag Harbor Cinema, The Bay Street Theater, Schiavoni's Market and Yoga Shanti. The house is a 12-minute walk to Haven's Beach. 1-minute around the corner from the house is Cavaniola's Wine, Cheese and Kitchen shops as well as the Sag Harbor Beverage store.

4.9 out of 5 average rating, 117 reviews
Guest favourite
A welcoming living area is illuminated by natural light from large windows. A comfortable gray sofa is complemented by light-colored armchairs and a coffee table adorned with books and decorative items. The neutral color palette is accentuated by indoor plants and a textured rug.
Home in Sag Harbor

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

4.95 out of 5 average rating, 323 reviews
Top Guest favourite
The main bedroom features a spacious bed with a white comforter and dark accent pillows. Sunlight filters through sheer white curtains covering French doors, leading to the outdoors. Bright wooden floors add warmth, while a ceiling fan offers comfort.
Apartment in Greenport

Lovely 2-bedroom apartment in a historic home

Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!

4.97 out of 5 average rating, 136 reviews
Top Guest favourite
A spacious living area features a brick fireplace with a mounted television above. Light-colored sofas are arranged around a wooden coffee table. Natural light enters through large windows, with a dining area visible in the background. Decorative lanterns adorn a rustic table.
Home in Shelter Island Heights

Laid Back Relaxation

Kick back and relax in this calm, stylish space. Nice newly updated home on a quiet street within walking distance to beaches, restaurants and a golf course. Great location near Shelter Island heights town, Crescent beach and Sunset beach. The location provides both privacy and relaxation at home with just a short walk or ride to popular Shelter Island spots.

5.0 out of 5 average rating, 22 reviews
Superhost
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.
Apartment in Shelter Island Heights

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

4.9 out of 5 average rating, 271 reviews

Popular amenities for Shelter Island family-friendly rentals

When is the best time to visit Shelter Island?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$1,069 NZD$886 NZD$996 NZD$1,060 NZD$1,008 NZD$1,200 NZD$1,289 NZD$1,289 NZD$1,069 NZD$1,018 NZD$933 NZD$993 NZD
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