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.

Cozy Town Cottage - Minutes from EH Town

This charming, historic home is perfect for a young family! The original mudroom with laundry, farm kitchen (no dishwasher), spacious dining and living rooms, two bedrooms and one bathroom welcome you on the main level. Upstairs is a larger bedroom and a second bathroom as part of an open primary suite. Take a half mile, tree-covered walk to town, or stop at the grocery store or restaurants just down the street. Sorry but, absolutely no animals as owner has severe allergy.

Waterfront Cottage with Dock

Arts and Crafts cottage on an ocean cove in Stonington with dock and close to the beaches. On same cove as Saltwater Farm Vineyard and nearby to Mystic Aquarium and Seaport, great restaurants, and Foxwoods and Mohegan Sun resorts. You’ll love the backyard and dock. I offer complimentary canoe, kayak and paddle board use so you can enjoy the water. Bring your own boat or rent one for 50% off at Stonington Marina. My place is good for couples, families with kids, and pets.

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.

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!

House in NL near CGA, Sub Base, Mohegan Casino

House is located in New London CT. Off I95 near Coast Guard Academy 3 mins, Connecticut College 4 mins, Mitchell 11 mins, Navy Base 9 mins,Yale L&M Hospital 10 mins, Branford House Avery Point 15 mins, Ocean Beach 16 mins, Millstone 19 mins, Mohegan 16 mins, Foxwoods 24 mins, Electric Boat 9 mins. Enjoy private house with full kitchen, and dining room for family get together. 20% Discount weekly stay. 35% on monthly stay

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.