Vacation rentals in Great South Bay

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!

Fire Island Pines: Studio Cabin

Studio cabin (approx. 13.5 x 15 ft.) Functional, basic, rustic, atmospheric—It's just a little cabin in the woods. The shack can accommodate only 2 people max. Queen bed (sheets, blankets) Bathroom (shower/towels) Kitchenette (fridge, microwave, sink, dishwasher, dishes, cutlery, glasses) A/C (window unit) Fan Basic tv Internet Beach chairs/umbrellas, Outside shower The Pines is primarily a gay community, but welcoming to all. We love our wild deer and squirrels but no pets in the cabin

All Private Bright Spacious Close to All

DISINFECTED AND CLEANED BEFORE YOU ARRIVE! Spacious ground level PRIVATE apt with lots of natural light. Full kitchen/new stove/fridge/Keurig.Bedrm- queen sz bed, living rm -full sz sofa sleeper. Also available is queen air mattress w/ topper. Washer/Dryer. Minutes away to the Port Jeff Village shops&restaurants/Ferry/LIRR, hospitals, & Stony Brook. Small beaches 10-15min drive, large beaches,Shop Outlets & Wineries 25 -60 minute. PLEASE NOTE: Extra $2 Daily Fee for charging electric car.

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.

Charming 2 Bedroom apartment

Enjoy our charming 2 Bedroom apartment that is in a quiet and friendly neighborhood in a cul-de-sac. Private entrance on first floor of our house with 2 Bedrooms, 1 Bathroom, Living room, Dining area, and a Kitchen. Close to: Main highways (Sunrise HWY/Long Island Expressway), Grocery stores, Winery & Vineyards, Davis park ferry, Downtown Patchogue village (Restaurants, bars, breweries, shopping), Beaches, Top Golf, MacArthur airport, Long Island Community Hospital, St Joseph’s College.

Private Studio in Lovely South Bayport

Studio offers a private, sequestered nook in quiet Bayport. The 350 sq ft. space offers: Queen bed (Drexel Heritage pillow-top mattress) with cotton bedding, 2 king pillows. Large bathroom with roomy shower, good towels. We use natural cleaners. Wifi, Roku television as well as contactless check-in/ out. Easy access. Close to ferries to FI beaches. Close to main street. Walk to two parks. Dedicated off-street parking. NO SMOKING. NO ANIMALS. Violations result in eviction/ fines imposed.

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.

Bay Shore's Private Guest Suite

Welcome to our cozy guest suite nestled within walking distance of the Fire Island ferries and conveniently close to local amenities! This private unit, attached to the main part of our home, offers a comfortable retreat for your stay. Step through your own private entrance into a welcoming living room, where you can unwind after a day of exploration. The bedroom features a queen-sized bed, providing a restful night's sleep, and an adjoining bathroom offers convenience and privacy.

Lovely brand new apt 2 min away from train station

Have a fun getaway at this stylish beautiful place. In a brand new home, super fast wifi for remote work for business travelers or family. Walking distance from train station and 5 minutes away from Huntington Historic Village or take a 45 min train ride to NYC. Enjoy all the local restaurants, shops, bars and Paramount theater. Do you want to take a flight around NYC on a private plane? Ask host for more details. Central AC/Heat 1GB wifi speed

Studio in Stony Brook

We have contactless check-in procedure & fully private entrance. Please contact with any questions! Large clean studio space that is totally private from the main residence. Private bathroom with toiletries included. Close to beaches, shopping, and SUNY hospital and campus by car or bus. Pull-out loveseat with twin size mattress available for an extra charge. (Book for “3 Guests” for this regardless of occupancy so we know to prepare the bed.)

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.