Family-friendly holiday rentals in Long Island

Luxurious Waterfront Beach House On The Bay

Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing and exclusive Great South Bay with private beach... The experience will bring you the feel of tranquility everyone desires with vacationing out east. While offering all the enjoyments the island has at your fingertips. Centrally located to all island destinations. 90 minutes from Manhattan - 15 minutes to West Hampton - 15 minutes to Fire Island Ferrys. Visit top winery’s WiFi

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

Joyful Beach House, viewing The Great South Bay

Amazing Great South Bay view with access to Shorefront and Rider Parks. This Ranch has an unobstructed view of the Shorefront Band Shell. Watch concerts and sunsets from the comfort of your patio. Walk down to the Patchogue Beach Club and enjoy the pool and beach. This open-concept home has 2 bedrooms, one bath, a remodeled bathroom, and a kitchen. The kitchen has stainless steel appliances, a farm sink, and a butcher block countertop with natural lighting that will brighten the home.

Boho Beach House

🌊WALK TO EVERYTHING🍹WELCOME TO THE WEST END STATE STREETS. This Boho inspired beach house is located in the heart of Long Beach, NY surrounded by restaurants, shopping and nightlife. Conveniently located only 2 blocks and a short walk to the beach, this newly renovated, fully furnished home includes garage parking, and all necessary living amenities to make for an easy summer living experience. ⛱️BEACH PASSES INCLUDED DURING SUMMER MONTHS (value of $120/day for 6 guests).

Beautiful Retreat by the Beach, La Casita Flora

Guest apartment has a private entrance and includes one bedroom, bathroom, kitchenette, office with sofa bed, and large sunny balcony. You can walk everywhere from here! It is a five minute walk to the beautiful beach and boardwalk. The train station to NYC and JFK is one block away. A grocery store, restaurants, coffee shop, brewery, pharmacy, and other amenities are minutes away. Many guests comment that I keep the space "sparkling clean".

Pura Vida LB - APT in heart of town right by beach

Second story apartment located in the ❤️ of town! •Walk across the street to the train station, grocery store, restaurants, banks, brewery etc. ☕️ Starbucks ON our corner (1 min) 🏖️ Beach(Edwards)/boardwalk 🍔Riptides 🏄 Skudin surf- All about 4 min walk No car needed 30 min from JFK Suitable for families! Beach supplies offered Please note : only 3 *adults* are included in booking. There will be additional charge(s) for extra adults

The Stella ~ A 1920s Beach Bungalow

Welcome to The Stella, a thoughtful 1920's home set in the heart of Bellport Village. This is the place for a summer romance, a family gathering, or a creative re-centering. Inspired by the subtle palette and refined geometry of the American artist Frank Stella—who often spent time on Long Island—The Stella enjoys close proximity to many beaches and wetlands. ~ ask about our monthly winter rates for 2025-2026 ~

Quaint Cottage on Long Island's South Shore.

The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

Beach, Dining and Relaxation in one spot!

This guest suite has one main bedroom with queen bed + a separate alcove with a bed that becomes two single beds. It is conveniently located one block from the LIRR train station. The beach and boardwalk are four blocks by foot and behind our street are dozens of restaurants, bars, coffee shops, grocers and pharmacies. We are available when you'd like, to ensure a pleasant and relaxing stay.