
Family-friendly vacation rentals in Shelter Island
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Shelter Island
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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 grouds are smoke-free.

East Hampton Village Fringe, Renovated with Pool
This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

Secluded Farmhouse - Studio Apartment Style Unit
Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

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!

Sag Harbor / Noyack Pad - private STUDIO apartment
500sq ft studio apartment, with private entrance, private bathroom, outdoor deck area with table/chairs, private kitchenette (but no stove). Close to Noyack Bay/Long Beach. 5 min drive to Sag Harbor village. 15 min to East Hampton village. 15 min to Ocean beaches. Responsive host: you will be greeted and handed keys when you arrive. No waiting around. Host will respond to all calls or messages rapidly if any issues arise. Lockbox entry with spare key also for 24 hour access

Sag Harbor Village Cottage with Pool
Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches, and tennis. 10 minute drive to Wolffer & ocean beaches. 4 bedrooms, 2 modern bathrooms and pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

The Sandpiper
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).

Greenport Beach house Mini Resort Spa & Catering
Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

Shelter Island Getaway with Cozy Fireplace
Just 2 blocks from Hay Beach, our family & pet-friendly 3BR home offers space to relax & play. Enjoy a large yard w/ fire pits, beach gear, games, & toddler toys. Inside: open living area, fireplace, full kitchen, 2 baths, playroom, workout space, & extra sleeping options. Quiet neighborhood, perfect for families. Winter stays: cozy up by the fire & enjoy $0 cleaning fee Nov–Mar. Host lives next door for quick support.

Exclusive Sag Harbor Compound
A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

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!

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
Popular amenities for Shelter Island family-friendly rentals
Family-friendly home rentals with a hot tub

Walk-To-The-Beach House In The Dunes

Private Oasis W/Stunning Vinyard and Pool Views

Greenport Village walking distance to all

Luxury cottage by the sea with hot tub and pool

By NYC & Hamptons - Hot Tub, Pool Table, Speakeasy

Montauk Waterfront Condo w/ Sunset Views

Oceanfront Retreat: Modern Beach House

1800 Historical EH Home, 1 Mile to Town, Hot Tub!
Family- and pet-friendly home rentals

Savor Ocean Sunsets at a Soothing Beachfront Haven

Fall Sale! Cozy Bungalow/Pet-friendly/Walk2Beach

Whaling Captain Pierson's Cottage

Breezy Waterfront Home With private Dock

Cozy Farmhouse Retreat in North Fork, NY

GREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH

Southampton Charmer, 5 bedrooms w pool - Location

Montauk Oceanview with Fireplace (2)
Family-friendly home rentals with a pool

Stylish+Cozy Hamptons Winter Getaway-5min to Beach

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

Beautiful Waterview Condo on the North Fork of LI

Classic Southampton Village Home w/ Pool

Waterfront Autumn Escape in Wine Country: 2BR

Beachside Waterview 2Br Condo w/ Pool in Greenport

CASA GYPSEA - a chic and peaceful 3 bedroom house

Luxury Hamptons Home with Heated Saltwater Pool
Quick stats about vacation rentals that are family-friendly in Shelter Island
Total rentals
120 properties
Nightly prices starting at
€ 103 before taxes and fees
Total number of reviews
2.1K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- Jersey Shore Vacation rentals
- Ocean City Vacation rentals
- The Hamptons Vacation rentals
- Rentals with a hot tub Shelter Island
- Rentals with a fireplace Shelter Island
- Beachfront rentals Shelter Island
- Rentals with beach access Shelter Island
- Rentals with a kayak Shelter Island
- Rentals with pools Shelter Island
- Rentals with a fire pit Shelter Island
- Pet-friendly rentals Shelter Island
- Rentals with outdoor seating Shelter Island
- Waterfront rentals Shelter Island
- Rentals with a patio Shelter Island
- House rentals Shelter Island
- Rentals with a washer and dryer Shelter Island
- Fitness-friendly rentals Shelter Island
- Family-friendly rentals Suffolk County
- Family-friendly rentals New York
- Family-friendly rentals United States
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Ocean Beach Park
- Walnut Public Beach
- Blue Shutters Beach
- Shinnecock Hills Golf Club
- Napeague Beach
- Cedar Beach
- Groton Long Point Main Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Sunken Meadow State Park
- Sandy Beach
- Jennings Beach
- Wildemere Beach
- Ninigret Beach
- Mystic Seaport Museum
- Outer Beach at Smith Point County Park