
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 $211 AUD 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, Wi-Fi 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.

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
KitchenFamilyBeach
4.92 out of 5 average rating, 100 reviews
Serene + chic ~ 8 mins to Main Street + beaches
The perfect Hamptons getaway! Near all of the best attractions. Enjoy this chic, serene home surrounded by the beauty of Hamptons nature + birds' chirping, deer sauntering. Cozy up to the wood burning fireplace, 80' TV + Chef's kitchen. Spark up the BBQ + firepit under the starry sky! Enjoy the bucolic views from every room. Here, you will be 8 minutes to Main St of East Hampton + Amagansett for endless dining + shopping options! Also 5-10 minutes to gorgeous beaches (great any time of year!).
FamilyKitchenGetting around
4.9 out of 5 average rating, 143 reviews
Mid-Century Gem with Pool. Steps to Private Beach.
Escape to our stylish mid-century modern retreat on Shelter Island. A 1 minute walk to stunning Crab Creek and a private neighborhood association beach, our home boasts 3 bedrooms, 2.5 baths and an outdoor shower, and sits on nearly an acre of secluded land. The backyard is a private oasis with towering trees, a bamboo forest and a large pool surrounded by beautiful landscaping. Enjoy an indoor fireplace in winter, an outdoor fireplace and grill in summer, or a beach bonfire under the stars.
FamilyIndoor spacesQuiet
5.0 out of 5 average rating, 12 reviews
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.
FamilyIndoor spacesView
4.93 out of 5 average rating, 138 reviews
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.
Indoor spacesFamilyCheck-in
4.9 out of 5 average rating, 130 reviews
Sea Roost
This private, two-cottage property contains a few of the last remaining original fisherman cottages at Hither Hills built in the 1940s. Set on a lush, private knoll - South of the Highway - Sea Roost boasts mature landscaping and is located steps to Montauk's quiet and secluded Hither Hills Beach. The property consists of a 2 bed/2 bath cottage with separate artist studio (Qn bed, kitchenette & full bath). Dogs negotiable with pet fee. IG @searoosts
KitchenIndoor spacesBarbecue
4.97 out of 5 average rating, 116 reviews
Bayfront 1BR/2BR detached guesthouse with pool
Perfect relaxing getaway for a couple or family. Bayfront 1BR/2BR fully detached guest house with gorgeous morning views. Property has saltwater pool + hot tub (open May -October) and bay access via private dock. Central to both north & south forks (wineries + Hamptons or Montauk just short drive away). Down the road from famous Shelter Island Sunset Beach + golf course. Come explore the beauty of the Hamptons without the stress!
Indoor spacesKitchenAir conditioning
4.97 out of 5 average rating, 79 reviews
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 spacesCheckout
4.93 out of 5 average rating, 55 reviews
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.
Indoor spacesKitchenLayout
4.95 out of 5 average rating, 324 reviews
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!
KitchenFamilyHospitality
4.97 out of 5 average rating, 138 reviews
Historic Designer Farmhouse - Warm Pool until Nov
Tucked away on a private lot, just minutes from East Hampton Village, Amagansett Village, and Indian Wells Beach, this 3-bedroom, 2.5-bath cottage features a heated saltwater pool & Mahogany outdoor open-sky shower - open May through October, fireside outdoor lounge area, and charming children’s playhouse - creating the perfect setting for relaxing days spent at home.
FamilyIndoor spacesComfort
4.99 out of 5 average rating, 274 reviews
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.
FamilyKitchenAccuracy
5.0 out of 5 average rating, 23 reviewsPopular amenities for Shelter Island family-friendly rentals
Family-friendly home rentals with a hot tub

Sprawling Hamptons Estate with Hot Tub & Amenities
KitchenIndoor spacesLocation
4.78 out of 5 average rating, 146 reviews
Pool|Golf Sim|HotTub|Movie|Games|Firepit|Golf Open
FamilyKitchenCheck-in
4.95 out of 5 average rating, 100 reviews
Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)
Indoor spacesKitchenCleanliness
4.92 out of 5 average rating, 514 reviews
Private Oasis W/Stunning Vinyard and Pool Views
KitchenIndoor spacesLocation
4.97 out of 5 average rating, 218 reviews
Steps to Beach • Hot Tub • Game Room • Water Views
KitchenFamilyComfort
4.99 out of 5 average rating, 112 reviews
Explore the Water & Woods at a Relaxing Retreat
FamilyIndoor spacesCheckout
4.98 out of 5 average rating, 147 reviews
Calf Creek Cottage (Water Mill/Bridgehampton)
KitchenIndoor spacesAccuracy
4.95 out of 5 average rating, 110 reviews
Greenport Village walking distance to all
Indoor spacesFamilyBackyard
4.99 out of 5 average rating, 211 reviewsFamily- and pet-friendly home rentals

The Cooper-Burke House
KitchenIndoor spacesHospitality
4.9 out of 5 average rating, 118 reviews
Southampton Charmer, 5 bedrooms w pool - Location
Indoor spacesFamilyOutdoor spaces
4.93 out of 5 average rating, 137 reviews
Pool Central Private Bridgehampton Home
FamilyIndoor spacesHospitality
4.93 out of 5 average rating, 109 reviews
Savor Ocean Sunsets at a Soothing Beachfront Haven
FamilyKitchenHospitality
4.98 out of 5 average rating, 184 reviews
Beach Barn w/ Heated Pool & Sauna - Dog Friendly
FamilyKitchenPets
4.93 out of 5 average rating, 143 reviews
Cozy Farmhouse Retreat in North Fork, NY
KitchenFamilyBiking
4.92 out of 5 average rating, 135 reviews
Stylish Farmhouse in North Fork
Indoor spacesFamilyGetting around
4.97 out of 5 average rating, 143 reviews
Silver Beach, 3 Bedroom cottage w/ pool
KitchenIndoor spacesAccuracy
4.91 out of 5 average rating, 56 reviewsFamily-friendly home rentals with a pool

Luxury Hamptons Home with Heated Saltwater Pool
FamilyKitchenWalkability
4.98 out of 5 average rating, 179 reviews
Ocean View Studio with King Bed
KitchenFamilyAir conditioning
4.89 out of 5 average rating, 140 reviews
Astounding Watermill 5 Bedroom home with Pool
FamilyKitchenBackyard
4.94 out of 5 average rating, 167 reviews
Private Hay Beach Retreat with Heated Pool
Indoor spacesFamilyTV
4.98 out of 5 average rating, 94 reviews
Newly Renovated w/ Pool, Hot tub & Fireplace
KitchenIndoor spacesCondition
4.91 out of 5 average rating, 35 reviews
Tranquil Southampton/Sag Harbor 5 Bedroom, Pool
FamilyIndoor spacesAmenities
4.98 out of 5 average rating, 51 reviews
Secluded Luxury: New Gunite Pool, Walk to Bay
FamilyKitchenCheck-in
5.0 out of 5 average rating, 58 reviews
Stylish Beach Getaway: pool & walking location
Indoor spacesKitchenAccuracy
4.88 out of 5 average rating, 24 reviewsWhen is the best time to visit Shelter Island?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $885 AUD | $734 AUD | $825 AUD | $878 AUD | $835 AUD | $994 AUD | $1,068 AUD | $1,068 AUD | $885 AUD | $843 AUD | $773 AUD | $822 AUD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Destinations to explore
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- Rentals with pools Shelter Island
- Pet-friendly rentals Shelter Island
- Rentals with a hot tub Shelter Island
- Rentals with beach access Shelter Island
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- Family-friendly rentals Suffolk County
- Family-friendly rentals New York
- Family-friendly rentals United States
- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- East Matunuck State Beach
- Cooper's Beach, Southampton
- Fairfield Beach
- Ocean Beach Park
- Charlestown Beach
- Mystic Seaport Museum
- Mystic Aquarium
- Southampton Beach
- Sunken Meadow State Park
- Soundview Beach
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Wölffer Estate Vineyard
- Ocean Beach
- Sleeping Giant State Park
- Meschutt Beach
- Orient Beach State Park
- Ditch Plains Beach
- Wesleyan University
- Long Island Aquarium
- Splish Splash Water Park





