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Family-friendly holiday rentals in Shelter Island Heights

Find and book unique family-friendly homes on Airbnb

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

  • Total holiday rentals

    Explore 350 holiday rentals in Shelter Island Heights

  • Nightly prices starting at

    Shelter Island Heights holiday rentals start at $214 AUD per night before taxes and fees

  • Verified guest reviews

    Over 12,870 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 120 rentals that welcome pets

  • Holiday rentals with a pool

    140 properties feature pools

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wi-Fi availability

    350 of Shelter Island Heights holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Shelter Island Heights rentals

  • 4.9 Average rating

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

Top-rated family-friendly rentals in Shelter Island Heights

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

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Top Guest favourite
Home in Shelter Island Heights

Surf Scoter Cottage Shelter Island

New heated gunnite Pool & pea gravel driveway. 4BR renovated mid-century ranch with a breezy nautical theme. Central A/C. Giant back deck: Propane & Charcoal BBQ, Jacuzzi, Hammock & glorious Outdoor Shower. Private front & back yards. Fab mirrored bar, sleek kitchen, double-sink master bath+full 2nd bath. Impressive vinyl collect & 4 speaker Bluetooth stereo, Piano, chill basement media room + ping pong & foosball! washer/dryer. 4 bikes, beach chairs, cooler & umbrella. $100 /dog sorry no cats

KitchenFamilyGetting around

4.92 out of 5 average rating, 100 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

A 1905 farmhouse with modern touches, Arthur's Vineyard is a cozy 3-bed, 2-bath home in walking distance of Greenport village's beaches, marina, restaurants and boutiques. An open plan living area, breezy decor and a large landscaped backyard for spending relaxed summer days and nights with your family and friends, including the 4-legged ones. Walk to the train station/jitney or take a short drive to the wineries & farm stands of the North Fork. Recent updates: central heat/AC & new bathrooms.

Indoor spacesFamilyComfort

4.92 out of 5 average rating, 136 reviews
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 spacesKitchenBeach

4.94 out of 5 average rating, 139 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

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

KitchenFamilyBeach

4.98 out of 5 average rating, 184 reviews
Top Guest favourite
A charming historic boathouse features a steeply pitched roof with shingle siding and decorative trim. A white picket fence surrounds the property, while blooming shrubs enhance the entrance. A balcony adorned with planters awaits above the front door, complementing the inviting facade.
Home in Greenport

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's with modern updates. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

Indoor spacesFamilyBackyard

4.97 out of 5 average rating, 123 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.

KitchenFamilyOutdoor spaces

4.89 out of 5 average rating, 131 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!

Indoor spacesFamilyLong stay

4.97 out of 5 average rating, 296 reviews
Guest favourite
A bright living room features a comfortable gray sofa against a neutral wall, complemented by a light-colored rug with geometric patterns. A wooden coffee table sits in front, with a lounge chair nearby. Natural light enters through multiple windows, creating a spacious feel.
Home in Greenport

The Sandpiper

100% Walking Score 1 block away from Village 3 blocks away from Beach. 1 block away from Shelter Island Ferry. Around the corner from Hampton Jitney & LIRR Newly renovated 2-Family Home! This is for rental of 1st floor apartment (only) plus cabana, plus outdoor jacuzzi. Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy.

FamilyKitchenTV

4.95 out of 5 average rating, 398 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.

FamilyIndoor spacesParks

4.93 out of 5 average rating, 55 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 spacesFamilyWi-Fi

4.97 out of 5 average rating, 138 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

FamilyIndoor spacesBackyard

4.9 out of 5 average rating, 273 reviews
Guest favourite
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.
Home in North Fork

Beach House in L.I. Wine Country

Time to wine 🍷 down and make your way to the scenic North Fork. A clean and clutter-free beach house awaits. The Navy House is centrally located in a quiet residential enclave, steps away from Norman E. Klipp Marine Park (aka Gull Pond Beach) and a short drive to Greenport’s Historic Village, vineyards and farmstands.

Indoor spacesFamilySleep quality

4.98 out of 5 average rating, 126 reviews

Popular amenities for Shelter Island Heights family-friendly rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.
Home in Greenport

Greenport Village walking distance to all

KitchenFamilyBarbecue

4.99 out of 5 average rating, 211 reviews
Guest favourite
A well-designed outdoor area features a pristine pool with colorful floats, bordered by a spacious deck. Lounge chairs, adorned in striped blue and white, provide comfortable seating under large umbrellas. The house is illuminated, showcasing a welcoming atmosphere amidst lush greenery.
Villa in East Hampton

Pool|Golf Sim|HotTub|Movie|Games|Firepit|Golf Open

KitchenIndoor spacesTV

4.95 out of 5 average rating, 101 reviews
Guest favourite
An open-concept living space features a modern dining area with a wooden table set for six, complemented by sleek metallic chairs. A comfortable sectional sofa is positioned across from a wall-mounted television, with a fireplace and green outdoor views visible through large windows.
Cottage in Bridgehampton

Calf Creek Cottage (Water Mill/Bridgehampton)

KitchenIndoor spacesGetting around

4.95 out of 5 average rating, 110 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

FamilyKitchenBeach

4.78 out of 5 average rating, 146 reviews
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

KitchenIndoor spacesLocation

4.97 out of 5 average rating, 218 reviews
Guest favourite
The exterior of a modern two-story home features a sleek white facade with large windows allowing for ample natural light. A covered porch provides a welcoming entrance, alongside neatly arranged greenery and stone pathway leading to the front door.
Home in Southampton

Southampton Village Newly Built Gem

KitchenIndoor spacesPool

4.97 out of 5 average rating, 103 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 spacesKitchenCheckout

4.98 out of 5 average rating, 148 reviews
Superhost
An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.
Home in Springs

East Hampton Oasis - Pool and Hot Tub

Indoor spacesKitchenHiking

4.83 out of 5 average rating, 144 reviews

Family- and pet-friendly home rentals

Guest favourite
A heated pool is framed by lush greenery and well-maintained grass, providing a serene environment. Two wooden loungers are positioned in foreground, inviting relaxation by the water. The surrounding trees create a private and tranquil space for guests to enjoy.
Home in North Fork

* Restored Farmhouse on the North Fork

FamilyIndoor spacesLayout

4.95 out of 5 average rating, 112 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

Indoor spacesFamilyCondition

4.9 out of 5 average rating, 119 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 spacesLocation

4.97 out of 5 average rating, 116 reviews
Guest favourite
A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.
Home in Springs

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Indoor spacesKitchenQuiet

4.89 out of 5 average rating, 134 reviews
Guest favourite
A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.
Home in Hampton Bays

Stunning Hamptons Waterfront Escape w/ Sunset View

Indoor spacesFamilyQuiet

4.87 out of 5 average rating, 144 reviews
Top Guest favourite
A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.
Home in Hampton Bays

Stylish + Modern Cozy Cape - 5 min to beach

KitchenFamilyBackyard

4.98 out of 5 average rating, 160 reviews
Top Guest favourite
The exterior of a historic Tudor home is shown, featuring a blend of brick and wood accents. A winding driveway leads to the entrance, surrounded by lush greenery and a decorative black fence. Trees provide shade, enhancing the serene outdoor setting.
Guest suite in North Fork

Walk to Vineyards, Beaches, Farms & Town

Indoor spacesFamilyGetting around

4.88 out of 5 average rating, 755 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

Central Private Bridgehampton Home

KitchenFamilyCheck-in

4.93 out of 5 average rating, 109 reviews

Family-friendly home rentals with a pool

Top 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

KitchenIndoor spacesBathroom

4.98 out of 5 average rating, 179 reviews
Superhost
A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.
Condo in Greenport

Waterfront Escape | Private Beach, Pool & Views

Indoor spacesFamilyParking

4.88 out of 5 average rating, 173 reviews
Guest favourite
A tranquil saltwater pool area is surrounded by lush greenery, featuring four sun loungers with colorful cushions. A large blue umbrella provides shade on the paved deck, enhancing the outdoor relaxation space.
Home in Springs

Fall-Getaway, WoodFireplace, Walk2Beach, Spotless

KitchenFamilyLayout

4.87 out of 5 average rating, 237 reviews
Guest favourite
Home in Shelter Island Heights

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

KitchenFamilyLayout

5.0 out of 5 average rating, 13 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

KitchenIndoor spacesWi-Fi

4.97 out of 5 average rating, 79 reviews
Guest favourite
A modern mid-century ranch house is set against a clear blue sky. Lush green grass surrounds the home, complemented by neatly trimmed shrubs. A paved pathway leads to the entrance, while trees provide a natural backdrop, enhancing the privacy of the property.
Home in Shelter Island Heights

Silver Beach, 3 Bedroom cottage w/ pool

KitchenIndoor spacesHeating

4.91 out of 5 average rating, 56 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

4.92 out of 5 average rating, 36 reviews
Top Guest favourite
Home in Greenport

Bayview house with salt water pool & private chef

KitchenFamilyParking

4.91 out of 5 average rating, 22 reviews

When is the best time to visit Shelter Island Heights?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$618 AUD$714 AUD$564 AUD$612 AUD$735 AUD$862 AUD$928 AUD$932 AUD$808 AUD$700 AUD$637 AUD$678 AUD
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