Kid-friendly vacation rentals in Wainscott

A spacious deck features wooden planks bordered by leafy green plants, providing a sunlit area for relaxation. A glass-enclosed room stands nearby, allowing for natural light to fill the space while offering a connection to the outdoors.

4.97 out of 5 average rating, 37 reviews

Waterfront Beach Cottage

Renovated New Suffolk Waterfront Beach Cottage steps from water/beach/restaurants & more w/ water views from practically every window in the heart of the most special neighborhood in the north fork. Perfect for families with twn over full bunks, pvt mstr, grill, outdr shower and new kitchen. Bonus room has comfy couches & sunset views. Dine al fresco with water views or stroll to restaurants, apple picking or famous New Suffolk beach. Minutes from everything your vacation could need, year round.

5 out of 5 average rating, 10 reviews

A spacious recreational area is presented with a foosball table and a dartboard. A wooden bunk bed with a mattress is positioned against the wall, along with several dressers for storage. Natural light is allowed through the adjacent windows, illuminating the room.

Home in Waterford

Seaside Rental Too

Relax with the whole family at this peaceful, beautiful, completely remodeled house just an 1200 foot walk to the beach. Close to shopping, movies, restaurants and many other attractions! Complete with all appliances, kitchen, TVs, Internet, 3 bedrooms, 2 full baths, living, dining, laundry, huge rec room and expansive deck. Beautiful large yard perfect for games or simply relaxing at the built in fire pit. So many fun and relaxing things to do within minutes from this great location!

4.93 out of 5 average rating, 109 reviews

A large, fenced-in backyard features a wooden playground with a slide and climbing structure, surrounded by lush greenery. Soft grass covers the ground, creating a safe play area for children. Mature trees provide natural shade in this private outdoor space.

Home in East Hampton

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.

Superhost

A stone pathway leads through lush greenery toward a tranquil pool area. Surrounding trees create a private setting, framing a wooden dining table and chairs arranged beside the pool, inviting relaxation in a serene outdoor environment.

Home in East Hampton

4.83 out of 5 average rating, 6 reviews

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.

A view of a spacious backyard is presented, featuring a hammock among lush green foliage and a fire pit surrounded by stones. Bright yellow chairs are arranged on a patio area. The backdrop includes a serene landscape with boats visible in the distance.

4.94 out of 5 average rating, 108 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.

4.88 out of 5 average rating, 102 reviews

A spacious living area is highlighted by warm wooden flooring and natural light from large windows. A stylish sofa faces a decorative coffee table, with a large framed portrait and a dining area visible in the background. The kitchen is accessible through a doorway.

Home in Mastic

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

Superhost

Home in Hampton Bays

4.94 out of 5 average rating, 18 reviews

Hamptons! Chic+Cozy Retreat! Location! Famfriendly

Welcome to our stylish and family-friendly Airbnb retreat, nestled in a serene neighborhood perfect for your next getaway! From the moment you step through the door, you'll be captivated by the modern yet inviting ambiance designed to cater to guests of all ages. From stylish interiors to thoughtful amenities and a convenient location, our family-friendly Airbnb offers the perfect blend of comfort and sophistication for an unforgettable vacation experience.

A spacious front yard features lush greenery beneath a large tree, providing shade. The inviting roadway leads toward a private beach area, creating a serene and accessible outdoor setting. The scene captures the tranquility of the neighborhood, framed by beautifully maintained landscapes.

5 out of 5 average rating, 22 reviews

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.

The spacious lower level showcases a foosball table, desk area with a chair, and a relaxed seating arrangement. Soft carpeting covers the floor, while recessed lighting brightens the room. A doorway leads to a bathroom, adding convenience for guests.

5 out of 5 average rating, 44 reviews

Immaculate NOFO Beach House Steps from Beach

Enjoy all the North Fork has to offer in this gorgeous, well stocked home. Nestled amongst 50+ vineyards/ breweries and the beautiful Peconic Bay (200 yards away!) the home is perfectly situated for your family to enjoy a relaxing vacation. Whether you are looking for a summer spent on the beach, a fall spent at harvest festivals or winter at the fire place vineyard tours, this is a great year round getaway.

Superhost

A rocky shoreline is framed by a silhouetted tree against a colorful sunset. Clouds display shades of pink and orange as the sun sets over the water, creating a serene atmosphere. The beach area offers a peaceful view of nature.

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

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$.

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

4.98 out of 5 average rating, 179 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.