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Family-friendly holiday rentals in Shelter Island

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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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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.

FamilyKitchenWalkability

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.

Indoor spacesKitchenWalkability

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.

KitchenIndoor spacesView

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!

FamilyKitchenNearby

4.98 out of 5 average rating, 241 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.

KitchenFamilySleep quality

4.9 out of 5 average rating, 129 reviews
Guest favourite
The front exterior of the bungalow is showcased, featuring a wooden fence that provides privacy and a garden filled with hydrangeas. The house displays large windows that invite natural light, set against a backdrop of gravel and greenery.
Home in Greenport

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

KitchenFamilyHospitality

4.97 out of 5 average rating, 295 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.

FamilyIndoor spacesCheckout

4.9 out of 5 average rating, 117 reviews
Guest favourite
The exterior of a two-story house is depicted, featuring a light-colored facade with a welcoming front porch. Clear blue skies and greenery surround the property, while the lawn is well-maintained, offering a spacious area in front of the house.
Home in Shelter Island

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.

KitchenFamilyHiking

4.93 out of 5 average rating, 54 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.

FamilyIndoor spacesCleanliness

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!

Indoor spacesFamilySleep quality

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.

FamilyKitchenHospitality

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

FamilyKitchenWi-Fi

4.9 out of 5 average rating, 271 reviews

Popular amenities for Shelter Island family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
A vibrant pool scene is captured, featuring a colorful unicorn float positioned on the water. Lush hydrangea blooms frame the area in shades of pink, complementing the surrounding greenery and the wooden fence that provides privacy.
Apartment in Southampton

Swimming pool w/Hot tub Fire Pit Coffee Bar

FamilyIndoor spacesHospitality

4.96 out of 5 average rating, 109 reviews
Top Guest favourite
A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.
Home in North Fork

Private Oasis W/Stunning Vinyard and Pool Views

FamilyIndoor spacesAccuracy

4.97 out of 5 average rating, 218 reviews
Guest favourite
A spacious living area features a dark leather sofa adorned with colorful throw pillows, complimented by a patterned area rug. A ceiling fan is positioned above, and natural light streams through multiple windows. An adjoining dining area with a black table and chairs is visible.
Home in Greenport

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

Indoor spacesFamilyQuiet

4.92 out of 5 average rating, 514 reviews
Guest favourite
Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

FamilyKitchenPool

4.96 out of 5 average rating, 184 reviews
Guest favourite
The image captures a spacious outdoor area featuring a large heated pool with a fountain and surrounding stone patio. Nearby, lounge chairs are arranged for relaxation, while a generous lawn stretches in the background, accompanied by a well-designed home nestled among trees.
Home in East Hampton

Sprawling Hamptons Estate with Hot Tub & Amenities

KitchenFamilyHeating

4.78 out of 5 average rating, 145 reviews
Top Guest favourite
A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.
Home in East Hampton

Explore the Water & Woods at a Relaxing Retreat

Indoor spacesKitchenGetting around

4.98 out of 5 average rating, 144 reviews
Guest favourite
A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.
Cottage in Guilford

Luxury cottage by the sea with hot tub and pool

Indoor spacesFamilyRiver

4.95 out of 5 average rating, 210 reviews
Top Guest favourite
Home in Branford

Steps to Beach • Hot Tub • Game Room • Water Views

KitchenFamilyComfort

4.99 out of 5 average rating, 109 reviews

Family- and pet-friendly home rentals

Guest favourite
A bright living room features a large white sofa and armchair, complemented by a wooden coffee table. A striking red artwork adorns the wall, while large windows allow natural light to fill the space. A dining area with a mirrored wall is visible in the background.
Home in North Fork

Stylish Farmhouse in North Fork

FamilyKitchenCheckout

4.97 out of 5 average rating, 143 reviews
Top Guest favourite
The exterior of the farmhouse is framed by well-maintained hedges, with a simple wooden staircase leading to the front door. Brightly lit windows are positioned symmetrically, highlighting the home's classic architecture. The surrounding greenery complements the inviting entrance.
Home in Greenport

Cozy Farmhouse Retreat in North Fork, NY

KitchenIndoor spacesBathroom

4.92 out of 5 average rating, 133 reviews
Guest favourite
A bright living area is furnished with a leather sofa and a dark coffee table, positioned on a textured rug. Natural light filters through large windows, illuminating the space. A staircase leads to an upper level, with wooden accents enhancing the modern design.
Home in Bridgehampton

Pool Central Private Bridgehampton Home

KitchenIndoor spacesCheckout

4.93 out of 5 average rating, 108 reviews
Top Guest favourite
A cozy living area features a light-colored sofa adorned with blue and white throw pillows. Woven armchairs flank a wooden coffee table, while a stone fireplace adds warmth. Two large windows allow natural light to fill the space, complemented by greenery and decorative accents.
Home in Montauk

Sea Roost

KitchenIndoor spacesDecor

4.98 out of 5 average rating, 115 reviews
Guest favourite
A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.
Home in Springs

Silver House: 3BR Home with Private Beach Access

FamilyKitchenAccuracy

4.95 out of 5 average rating, 523 reviews
Top Guest favourite
A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.
Cottage in Riverhead

Savor Ocean Sunsets at a Soothing Beachfront Haven

FamilyKitchenWalkability

4.98 out of 5 average rating, 182 reviews
Guest favourite
The backyard showcases a serene oasis with a sparkling pool surrounded by lush greenery. A sunroom is visible, providing a view of the inviting outdoor space. The setting offers a sense of privacy, enhanced by the natural landscape.
Home in Springs

Oasis backyard, Pool, Gym, and Sunroom!

KitchenIndoor spacesAmenities

4.94 out of 5 average rating, 106 reviews
Guest favourite
A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.
Home in Shinnecock Hills

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

KitchenIndoor spacesOutdoor spaces

4.95 out of 5 average rating, 204 reviews

Family-friendly home rentals with a pool

Guest favourite
An expansive view of the ocean under a bright blue sky, featuring wispy clouds. The shoreline is lined with gentle waves, and a grassy area is visible in the foreground, leading down to the water.
Condo in Greenport

Sound Front Condominium

FamilyIndoor spacesDecor

4.89 out of 5 average rating, 282 reviews
Guest favourite
A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.
Home in Westhampton Beach

Luxury Hamptons Home with Heated Saltwater Pool

Indoor spacesKitchenLayout

4.98 out of 5 average rating, 173 reviews
Top Guest favourite
A spacious backyard is highlighted by a blue in-ground pool surrounded by lounge chairs. Red umbrellas provide shade, while a tall wooden fence adds privacy. Lush green grass complements the natural setting, and a rustic home is visible in the background among the trees.
Home in Springs

Private & Pristine with Pool and Kid’s Playard

FamilyKitchenTV

4.93 out of 5 average rating, 140 reviews
Top Guest favourite
The living area features two rattan chairs facing a coffee table, surrounded by vibrant wall art. A cozy sofa and plants add life to the space. Natural light streams through large windows, creating a bright and inviting atmosphere.
Home in Montauk

3 BR/Pool. Walk to Beach & Town!

Indoor spacesKitchenLaundry

4.98 out of 5 average rating, 132 reviews
Top Guest favourite
A spacious house is framed by lush landscaping, featuring a large pool in the foreground. Sun loungers and patio umbrellas are arranged around the pool, along with a pink float. The exterior showcases a combination of shingle siding and solar panels under a clear blue sky.
Home in Shelter Island Heights

Beautiful beach home with pool & water views!

FamilyKitchenLayout

4.95 out of 5 average rating, 79 reviews
Guest favourite
Home in Shelter Island Heights

Mid-Century Gem with Pool. Steps to Private Beach.

Indoor spacesFamilyView

5.0 out of 5 average rating, 11 reviews
Top Guest favourite
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.
Guesthouse in Shelter Island Heights

Bayfront 1BR/2BR detached guesthouse with pool

KitchenFamilyQuiet

4.97 out of 5 average rating, 79 reviews
Top Guest favourite
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.
Home in Shelter Island Heights

Newly Renovated w/ Pool, Hot tub & Fireplace

Indoor spacesKitchenTV

4.91 out of 5 average rating, 35 reviews

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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Destinations to explore