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Kid-friendly vacation rentals in Shelter Island

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Shelter Island

Guests agree: these kid-friendly rentals 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.

Cottage in Guilford

4.93 out of 5 average rating, 264 reviews

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

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 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.

Guest suite in Montauk

4.94 out of 5 average rating, 124 reviews

Cozy guesthouse in an English style Tudor house

Light and airy, lots of blue and white (think Ralph Lauren) cozy and country feeling cottage in an English tudor house. The perfect place for a relaxing stay in Montauk. Reminiscent of an English county cottage with all its charm and imperfections. Its the perfect spot for a BBQ and relaxing outside with the sounds of birds chirping and the leaves rustling. 20 min walk to town, 25 min walk to the beach. I hope you'll enjoy your stay :)

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Monday-Thursday stays February through June no cleaning fees!!!

Home in North Fork

4.98 out of 5 average rating, 171 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

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

Cottage in Shelter Island

4.96 out of 5 average rating, 104 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

Vacation rentals for every style

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Spaces that are more than just a place to sleep

Popular amenities for Shelter Island kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Home in Center Moriches

4.74 out of 5 average rating, 61 reviews

Sunny little house in beach community!

Home in Wading River

4.96 out of 5 average rating, 488 reviews

Your Zen Retreat

Home in Water Mill

4.92 out of 5 average rating, 120 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

Home in Sag Harbor

4.85 out of 5 average rating, 159 reviews

Sag Harbor House for rent.

Home in North Fork

4.98 out of 5 average rating, 243 reviews

The Greenport Bungalow

Home in Southampton

4.96 out of 5 average rating, 119 reviews

4 Bed, 2 Bath, Southampton, L.I.

Home in Westhampton Beach

4.97 out of 5 average rating, 61 reviews

Brand new house with an all year round hot tub.

Home in Old Saybrook

4.97 out of 5 average rating, 118 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Kid-friendly apartment rentals

Rental unit in Montauk

4.9 out of 5 average rating, 217 reviews

Montauk Beach Bungalow West

Rental unit in Sag Harbor

4.83 out of 5 average rating, 183 reviews

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

Rental unit in Old Saybrook Center

4.96 out of 5 average rating, 120 reviews

Convenient and Cute in Downtown Old Saybrook

Rental unit in New Haven

4.91 out of 5 average rating, 171 reviews

Tranquil Apartment with Waterview, Walk to Beach!

Rental unit in North Fork

4.96 out of 5 average rating, 140 reviews

Upscale Newly Constructed Apartment

Rental unit in West Haven

4.92 out of 5 average rating, 190 reviews

Perfection! 2 Bedroom Apt. Friends or Family!

Rental unit in Southampton

4.87 out of 5 average rating, 127 reviews

Southampton Village Studio

Rental unit in West Haven

4.9 out of 5 average rating, 480 reviews

entire, private apartment close to the beach

Kid-friendly condo rentals

Condo in North Fork

4.83 out of 5 average rating, 124 reviews

Seaside Escape w Pool, Private Beach + Patio

Condo in Montauk

5 out of 5 average rating, 210 reviews

Montauk Waterfront Condo w/ Sunset Views

Condo in North Fork

4.88 out of 5 average rating, 147 reviews

Beautiful Waterview Condo on the North Fork of LI

Condo in North Fork

5 out of 5 average rating, 107 reviews

"Breathtaking Waterfront Water's Edge view"

Condo in Hampton Bays

4.95 out of 5 average rating, 42 reviews

A Unique Piece of Paradise, Water Front pool

Condo in Sag Harbor

4.88 out of 5 average rating, 68 reviews

Cute cottage apartment upstairs in Sag

Condo in North Fork

4.92 out of 5 average rating, 137 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Condo in East Hampton

4.82 out of 5 average rating, 74 reviews

Private Newly built Modern East Hampton Apartment!

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

Total rentals
20 properties
Nightly prices starting at
$350 before taxes and fees
Total number of reviews
570 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool

Destinations to explore