Become a host

Family-friendly vacation rentals in Shelter Island Heights

Find and book unique family-friendly homes on Airbnb

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

  • Total vacation rentals

    Explore 350 vacation rentals in Shelter Island Heights

  • Nightly prices starting at

    Shelter Island Heights vacation rentals start at ﺩ.ﺇ 551 per night before taxes and fees

  • Verified guest reviews

    Over 12,870 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 120 rentals that welcome pets

  • Vacation 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 vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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.

1 of 1 pages1 / 1
Top guest favorite
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

KitchenIndoor spacesAccuracy

4.92 out of 5 average rating, 100 reviews
Top guest favorite
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.

FamilyKitchenValue

4.92 out of 5 average rating, 136 reviews
Guest favorite
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.

KitchenFamilyWifi

4.93 out of 5 average rating, 138 reviews
Superhost
Home in North Fork

Bungalow by the Bay

SMOKE FREE • ALLERGY FREE Rates Include a 15.5% AirBB Service Fee Early Check In & Late Check Out Bungalow by the Bay is an Inhabitable Work of Art, recrafted by owner architects. The design is inspired by all of the beauty of coastal living, incorporating organic and natural elements and environmentally conscious technology, to create a happy and healthy living space. Bungalow by the Bay is ideal for those who love sunrises, nature, water, fine wine, delicious food and dreamy sunsets.

KitchenIndoor spacesBackyard

5.0 out of 5 average rating, 4 reviews
Top guest favorite
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.

Indoor spacesFamilyCheck-in

4.98 out of 5 average rating, 184 reviews
Top guest favorite
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.

FamilyIndoor spacesQuiet

4.97 out of 5 average rating, 123 reviews
Guest favorite
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.

KitchenFamilyComfort

4.9 out of 5 average rating, 130 reviews
Guest favorite
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, 296 reviews
Guest favorite
A cozy living area features a brown sectional sofa adorned with patterned throw pillows. A black coffee table sits on a striped area rug, providing a neutral contrast to the light hardwood flooring. Natural light filters through multiple windows, enhancing the welcoming ambiance.
Apartment in Greenport

Harbor Heights

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 2nd 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.

Indoor spacesKitchenAmenities

4.94 out of 5 average rating, 248 reviews
Top guest favorite
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 spacesFamilyQuiet

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

Indoor spacesKitchenTV

4.9 out of 5 average rating, 273 reviews
Guest favorite
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.

KitchenFamilyCheckout

4.98 out of 5 average rating, 126 reviews

Popular amenities for Shelter Island Heights family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
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

KitchenIndoor spacesBiking

4.99 out of 5 average rating, 211 reviews
Guest favorite
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

FamilyIndoor spacesTV

4.95 out of 5 average rating, 101 reviews
Guest favorite
Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

KitchenIndoor spacesDecor

4.96 out of 5 average rating, 189 reviews
Guest favorite
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)

Indoor spacesKitchenLocation

4.95 out of 5 average rating, 110 reviews
Guest favorite
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

FamilyIndoor spacesLocation

4.97 out of 5 average rating, 103 reviews
Guest favorite
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 spacesBeach

4.97 out of 5 average rating, 218 reviews
Top guest favorite
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

KitchenFamilyTV

4.98 out of 5 average rating, 148 reviews
Guest favorite
A cozy bedroom features a queen bed with a light blue quilt and a green loveseat nearby. Natural light enters through sliding glass doors, revealing a serene outdoor space. A decorative plant and framed artwork add a touch of interest to the room.
Guesthouse in East Hampton

Detached bungalow w/ private bath

Indoor spacesFamilyValue

4.83 out of 5 average rating, 355 reviews

Family- and pet-friendly home rentals

Guest favorite
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

KitchenIndoor spacesSleep quality

4.97 out of 5 average rating, 143 reviews
Guest favorite
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 spacesKitchenLocation

4.89 out of 5 average rating, 133 reviews
Top guest favorite
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 spacesFamilyPets

4.9 out of 5 average rating, 119 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)

Indoor spacesFamilyDecor

4.86 out of 5 average rating, 139 reviews
Guest favorite
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 spacesKitchenCheck-in

4.87 out of 5 average rating, 144 reviews
Guest favorite
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

FamilyKitchenTV

4.93 out of 5 average rating, 109 reviews
Top guest favorite
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 Cape w/Saltwater Pool-5min to Beach

FamilyKitchenComfort

4.97 out of 5 average rating, 159 reviews
Top guest favorite
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

FamilyKitchenHiking

4.88 out of 5 average rating, 755 reviews

Family-friendly home rentals with a pool

Top guest favorite
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 spacesKitchenAmenities

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 spacesFamilyDecor

4.88 out of 5 average rating, 173 reviews
Top guest favorite
A comfortable living room area is presented, featuring a light-colored sectional sofa arranged around a wooden coffee table. Natural light enters through a large window, illuminating a piece of artwork on the wall and adding a cozy touch to the space.
Apartment in Sag Harbor

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

FamilyIndoor spacesCondition

4.93 out of 5 average rating, 158 reviews
Guest favorite
A living area features shiplap walls and ample natural light from large windows. A dark sectional sofa is positioned next to a glass coffee table with a small plant. An open kitchen area is visible, along with access to a screened porch through sliding doors.
Condo in Greenport

Beautiful condo on Long Islands Northfork

Indoor spacesKitchenCheck-in

4.86 out of 5 average rating, 136 reviews
Guest favorite
A spacious backyard is showcased with a large saltwater pool, featuring a floating inflatable and sun loungers arranged along the edge. The house stands in the background, framed by trees and an inviting grassy area, enclosed by a black fence.
Home in Hampton Bays

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

KitchenIndoor spacesAccuracy

4.94 out of 5 average rating, 119 reviews
Guest favorite
Home in Shelter Island Heights

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

KitchenFamilyOutdoor spaces

5.0 out of 5 average rating, 13 reviews
Top guest favorite
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 spacesFamilyLayout

4.92 out of 5 average rating, 36 reviews
Top guest favorite
Home in Greenport

Bayview house with salt water pool & private chef

FamilyIndoor spacesComfort

4.91 out of 5 average rating, 22 reviews

When is the best time to visit Shelter Island Heights?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 1,590ﺩ.ﺇ 1,836ﺩ.ﺇ 1,451ﺩ.ﺇ 1,576ﺩ.ﺇ 1,891ﺩ.ﺇ 2,218ﺩ.ﺇ 2,387ﺩ.ﺇ 2,398ﺩ.ﺇ 2,079ﺩ.ﺇ 1,800ﺩ.ﺇ 1,638ﺩ.ﺇ 1,744
Avg. temp0°C1°C4°C10°C16°C21°C24°C24°C20°C14°C8°C3°C

Destinations to explore