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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.

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.

Home in North Fork

4.91 out of 5 average rating, 101 reviews

North Fork Escape - Walk To Village, Beach, Parks

Modern & cozy 3-bedroom, 2-bathroom farmhouse, dating back to 1905 and in walking distance of Greenport village and its many attractions. Large, landscaped & fully fenced private backyard for relaxed summer days and nights. Wood burning fireplace for the cooler months. Walk to the great bars & restaurants, beaches, train station/jitney & a short drive to the wineries & farm stands of the North Fork. Central heat & AC with new baths added in 2022.

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).

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

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

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 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 East Hampton

4.94 out of 5 average rating, 72 reviews

Family Friendly Springs Beach House

Home in Hampton Bays

4.96 out of 5 average rating, 91 reviews

Stylish+Cozy Hamptons Winter Getaway-5min to Beach

Home in Southampton

4.96 out of 5 average rating, 119 reviews

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

Home in Shirley

4.9 out of 5 average rating, 134 reviews

Cope near the beach

Home in Westhampton Beach

4.97 out of 5 average rating, 61 reviews

Brand new house with an all year round hot tub.

Kid-friendly apartment rentals

Rental unit in North Fork

4.82 out of 5 average rating, 119 reviews

House on First

Rental unit in Westhampton Beach

4.94 out of 5 average rating, 104 reviews

NEW, steps to the village 1 mile to Dune Road

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 North Fork

4.96 out of 5 average rating, 140 reviews

Upscale Newly Constructed Apartment

Rental unit in Shelter Island Heights

4.91 out of 5 average rating, 245 reviews

Squire Chase House

Rental unit in North Fork

4.96 out of 5 average rating, 118 reviews

Bright, Southold Studio Apt near beach & town

Rental unit in Sag Harbor

4.92 out of 5 average rating, 145 reviews

Whaling Captain Pierson's Apartment TOO

Rental unit in North Fork

4.97 out of 5 average rating, 232 reviews

Greenport Village View - Walk Downtown 2BR/1BA

Kid-friendly condo rentals

Condo in North Fork

4.82 out of 5 average rating, 97 reviews

Beautiful condo on Long Islands Northfolk

Condo in North Fork

4.83 out of 5 average rating, 124 reviews

Seaside Escape w Pool, Private Beach + Patio

Condo in North Fork

4.88 out of 5 average rating, 147 reviews

Beautiful Waterview Condo on the North Fork of LI

Condo in Bridgehampton

4.88 out of 5 average rating, 17 reviews

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

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

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