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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.

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Home in Hampton Bays

4.88 out of 5 average rating, 226 reviews

Nautical Cottage Near Beach, Wineries, Golf, Shops

Coastal themed cottage located in the center of The Hamptons. Super Hosts! Great WiFi. Bright & comfortable space! Cowfish/Canoe Place Inn closeby! Near WINERIES, BEACHES, GOLF, WATERFRONT RESTAURANTS, & SHOPPING. 4 bedroom areas 2 full baths & outdoor shower. Spacious backyard w/ fire pit & deck w/ string lights. Lot's to do each season for couples, friends, coworkers & families. Everything you need & want in a Hampton's home. Large screen TVs/Roku, Foosball. Access to loft bedroom by ladder.

Home in Sag Harbor

4.9 out of 5 average rating, 182 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence and gates around pool. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

Home in East Hampton

4.87 out of 5 average rating, 203 reviews

Heated SW Pool, Walk2Beach, 5*Yard4Pup, Spotless

Meticulously cleaned home. Tranquil family neighborhood in historic artist's beach community. Wood burning fireplace. Private fenced-in backyard . Heated saltwater pool in summer. Half mile to private bay beach, bike great trails & savor delicious meals prepared in fully equipped kitchen. Don’t miss Clearwater Beach's stunning sunset. Easy living home.Welcoming to all respectful families & guests.East Hampton's best restaurants are nearby. Smoke free.Small dogs permitted.Rental Registry 23-625.

Guesthouse in Southampton

4.96 out of 5 average rating, 439 reviews

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in an easily accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station and a 5 min. walk to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet!

Home in Water Mill

4.91 out of 5 average rating, 106 reviews

Peaceful 1850s barn w/Pool

Family, friends and work-friendly 3000 sq ft house set in 1.7 quiet acres off private driveway. Large garden and fenced pool area w/heated pool (season). Sleeps 8 in 4 bedrooms with 3 bathrooms. A simple but stylishly furnished house, very comfortable and easy to enjoy. Fresh in summer, cozy with log fires in the winter. Minutes from beautiful beaches, Water Mill's historic charm, the Hampton Classic and the visual & performing arts. Well-behaved pets with thoughtful owners are welcome.

Bungalow in Hampton Bays

4.98 out of 5 average rating, 110 reviews

Hamptons Waterfront- Relax & Getaway!

My place is right on the water with your own sandy beach. A quick walk to the restaurant and dining. No worries about having a drink and getting home. You’ll love my place because of the location and the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Conveniently located just minutes from the center of town for all your shopping needs; grocery store, Starbucks, 7-11, rite-aid, bagel cafe, pizzaria, farmers market and more.

Home in North Fork

4.98 out of 5 average rating, 201 reviews

Aqua Vista

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).

Home in North Fork

4.93 out of 5 average rating, 103 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

Home in East Hampton

4.93 out of 5 average rating, 107 reviews

Private & Pristine with Pool and Kid’s Playard

INSTANT BOOK: Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Pool open: Memorial Day - Labor Day Only.

Home in North Fork

4.98 out of 5 average rating, 243 reviews

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!

Home in North Fork

4.9 out of 5 average rating, 200 reviews

Greenport Beach House

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).

Guesthouse in Shelter Island

4.96 out of 5 average rating, 115 reviews

Waterfront carriage house studio

Access to endless pool/spa, private beach around corner, breathtaking views, access for kayak, sup etc on property, playful friendly dog, easy access to all including sunset beach, beautiful breeze, private location, 46 foot classic powerboat available for charter at discounted rate w/ rental

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Popular amenities for Shelter Island family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Home in North Fork

4.97 out of 5 average rating, 201 reviews

Private Oasis W/Stunning Vinyard and Pool Views

Home in North Fork

4.94 out of 5 average rating, 16 reviews

Chic Beach House: Waterfront, Vineyards, Hot Tub

Home in Wading River

4.96 out of 5 average rating, 488 reviews

Your Zen Retreat

Home in Sag Harbor

4.96 out of 5 average rating, 91 reviews

Sag village, 4 en-suite BRs, hot tub, beach 5 mins

Home in East Hampton

4.94 out of 5 average rating, 72 reviews

Family Friendly Springs Beach House

Cabin in North Fork

4.86 out of 5 average rating, 97 reviews

Beach & Forest: Cozy Cabin, Hot Tub, Peloton

Home in Shelter Island

4.88 out of 5 average rating, 24 reviews

NEWLY RENOVATED W/ POOL & FIREPLACE

Home in Southampton

4.83 out of 5 average rating, 210 reviews

Cozy & Chic Summer Getaway near village/beaches

Family- and pet-friendly home rentals

Cottage in North Fork

4.97 out of 5 average rating, 149 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Home in East Hampton

4.89 out of 5 average rating, 109 reviews

Gorgeous East Hampton Getaway

Home in Sag Harbor

4.85 out of 5 average rating, 159 reviews

Sag Harbor House for rent.

Rental unit in Sag Harbor

4.83 out of 5 average rating, 183 reviews

Pet friendly Apt. Plus cabin, EV charger & sauna.

Home in East Hampton

4.95 out of 5 average rating, 225 reviews

Private beach Historical House with large property

Home in East Hampton

4.94 out of 5 average rating, 155 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Cottage in Montauk

4.92 out of 5 average rating, 248 reviews

Montauk Oceanview Studio 6

Rental unit in Sag Harbor

4.92 out of 5 average rating, 145 reviews

Whaling Captain Pierson's Apartment TOO

Family-friendly home rentals with a pool

Home in East Hampton

4.97 out of 5 average rating, 31 reviews

Pretty East Hampton Village Fringe - Hansom Hills

Home in North Fork

4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

Home in Hampton Bays

4.94 out of 5 average rating, 121 reviews

Peaceful Retreat in Immaculate Architect’s House

Home in East Hampton

4.98 out of 5 average rating, 55 reviews

Summer Fun Modern Light Filled Hamptons House!

Home in East Hampton

4.74 out of 5 average rating, 89 reviews

Clean Home Pool Cent-Loc. Quiet Reserve Pet Friend

Home in Southampton

4.94 out of 5 average rating, 270 reviews

Southampton Village Classic-Summer Special!

Home in East Hampton

5 out of 5 average rating, 33 reviews

Stunning Central E. Hampton Home w/ gunite pool.

Home in East Quogue

4.95 out of 5 average rating, 77 reviews

Walker House

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

Total rentals
110 properties
Nightly prices starting at
$120 before taxes and fees
Total number of reviews
1.8K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
60 properties have a dedicated workspace

Destinations to explore