Kid-friendly holiday rentals in Shelter Island Heights

Private & Pristine with Pool and Kid’s Playard

INSTANT BOOK/ dates are current. 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! Heated Pool open: Memorial Day - Sept 30.

Relax or roam from our private spacious home

Bright and sunny newly renovated second and third floor of house built in late 1800s. Three blocks from Mystic Seaport, a short walk to downtown Mystic. Off street parking on the side of the house. House has plenty of space with two bedrooms plus a bonus room with a queen size futon. I Homey and comfortable to make you feel you can put your feet up and relax. User friendly. First floor is used as an office only on weekdays. Only 1/2 mile from Mystic Amtrak station, an easy walk.

Mystic Harbor Getaway - Best Spot Downtown

Walk out your front door and enjoy quintessential coastal New England. This family friendly apartment is on a quiet street and a 4 minute walk from all the main attractions. Grab a coffee at the renown Sift bakery and watch the boats navigate the historic Bascule Drawbridge. Meander along the placid Mystic River with breathtaking views of the Seaport and the Charles Morgan. The perfect spot to enjoy Mystic. There is another unit on the first floor. Yard is a shared space.

Historic charm & modern luxury in downtown Mystic

We are long-time AirBNB guests who have tried to create the home we are always looking to book -- family friendly with modern amenities. Open floor plan on the main level, new heat and air con throughout the house, three bedrooms and family bathroom on the second floor. Art supplies, toys and children's books all ready for you as well as a pack n play and booster seat. Backyard oasis with pergola, walking distance to drawbridge. Pets considered on a case by case basis.

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.

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Seaport Sanctuary: walking distance to downtown Mystic

Enjoy a family friendly getaway, centrally located in Mystic. Just a short walk from downtown Mystic and an even shorter walk to the Mystic Seaport. The Mystic Aquarium and Mystic Village are also both only 1.5 miles away from the house, making it a very quick drive there. Free on-site parking for 2 to 3 vehicles, depending upon size. Come see why USA Today named Mystic as the 4th best travel destination in the entire country!

NoFo Family Beach House — Walk To Private Beach

Nestled on the beautiful North Fork of Long Island, our family-friendly vacation home is a tranquil haven for wine enthusiasts and beach lovers alike. This updated, four-bedroom home offers the perfect blend of comfort and charm, ensuring a memorable escape for your family and friends. Explore the region's wineries and vineyards, savor in local farm to table cuisine, and create special memories with your loved ones.

There's a 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. Cleaning fees for winter stays are 0$.