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Summer Rentals on Long Island

Long Island has been known for many decades as being the summer spot that draws celebrities and elite from around the world. With some of the world’s most beautiful beaches, Long Island has quite a few summer rental properties and areas.

Internationally reputed for stunning beaches and vibrant summer crowds, the famous “Hamptons” are one of Long Island’s prime locations for summer rentals and rental homes. Long Island’s best summer rentals are the ultimate get away offering the advantage of being a short driving distance from the major metropolitan New York City and Manhattan.

The best advice for snagging a great summer rental is don’t wait too long to secure your rental! The best property locations are often snapped up early. Choice locations from Westhampton to Sagaponack, Amagansett, East Hampton, Southampton and Watermill all offer beautiful properties and boast nearby sprawling mansions of the rich and famous.  Rental properties in western areas and south of the highway are rented out quickly and tend to be on the higher end of the budget, offering easy access to main highways and located closest to the ocean. For less of a budget buster, try north of the highway and further out east on the south fork.

You can typically choose to rent a property for either the entire summer season, from Memorial Day to Labor Day, on a monthly  or weekly basis, or during off season months. The east end of Long Island is truly beautiful any time of year, and offers fine dining, boutique shopping, local wineries and farm stands, the Montauk lighthouse and state parks to explore or hike in, horseback riding on the beaches, activities such as surfing, boating and paddleboarding. Most of these activities are available year round.

Other hot summer rental areas on Long Island include Montauk Point, Orient Point, Fire Island’s beach front communities, Jones Beach Island and the town of Long Beach to name a few.

One of the most famous summer rental hotspots is Fire Island, a 31 mile long barrier island off the south shore. Spanning between Robert Moses State Park and the Moriches Inlet, Fire Island can be accessed from the Robert Moses Parkway on the west end and the William Floyd Parkway on the east end, but the beachfront towns and villages in between are accessible only by boat, seaplane, water taxis or ferries out of Bayshore, Sayville and Patchogue. Established as a nationally protected seashore in 1964, cars are not permitted anywhere else on the island. Each town has wooden or concrete boardwalks for pedestrian traffic and most towns allow the use of bicycles. Properly permitted school buses and vehicles for year round residents or contractors can access these shorefront towns by traversing the sandy shores with four wheel drive vehicles at certain times of the year; four wheel drive emergency vehicles are permitted year round and are often seen patrolling the beaches.


Each enchanting beachside town or incorporated village offers a different social scene. The oceanfront towns include Kismet, Seabay Beach, Saltaire, Fair Harbor, Dunewood, Lonelyville, Atlantique Beach, Atlantique, Robins Rest, Corneille Estates, Ocean Beach, Seaview, Ocean Bay Park, Point O’ Woods, Oakleyville, Sailors Haven which includes the Sunken Forest, Cherry Grove, Fire Island Pines, Water Island and Davis Park. Some areas provide solitude in quaint summer cottages and little or no active nightlife and social activities, while other areas such as Ocean Beach and the Fire Island Pines are reputed for their thriving social dynamics and nightlife.

The social hub of Fire Island is most definitely the incorporated village of Ocean Beach, originally settled in 1908. This family friendly beach town is known for an extensive commercial district that notably includes waterfront dining, various restaurants, a variety of shopping boutiques, a gym, a deli, an antiques dealer, ice cream shop, pizza place, liquor store and bakery, as well as dance clubs and bars featuring live music. Most of the communities 600 homes are original and date back to the early 1900’s. Both bayside and oceanfront beaches offer full lifeguard protection for swimmers and has the best fire department on Fire Island; strict codes are in place in the village and are enforced by the Suffolk County Police department so unruly visitors beware, you will be ticketed and put on the next water taxi back to the main land. The village is fully equipped with two tennis courts, a ball field, basketball court, playground, youth programs, two long established churches and boasts a large population, numerous summer rentals and “day trip” visitors, especially during the summer months.

The birthplace of Fire Island as it is known today is Cherry Grove, where the first residence was built and the first hotel opened in 1880. Both Cherry Grove and the Fire Island Pines, known as “The Pines”, have been famously LGBT friendly, symbolizing un-inhibited social freedom and catering to gay and lesbian vacationers since the 1960’s. Known worldwide, the Fire Island Pines contains some of the island’s most beautiful mansions, hotels and properties featuring two thirds of Fire Island’s in-ground pools. Celebrity residents and visitors to The Pines have included Calvin Klein, David Geffen,  Michael Lucas, Donna Summer, Scott Bromley (Designer of Studio 54) Elton John, Elizabeth Taylor, Betty Grable, even the much younger cousin of Franklin Delano Roosevelt, Laura Delano Eastman.

Summer rentals at Cherry Grove offer visitors many beachside properties to choose from, both close to and away from the nightlife. Do be sure to secure your rental as early as possible; rentals are always snapped up quickly and typically hard to find mid season. Cherry Grove is generally a warmly welcoming, accepting and friendly summer mecca for all types of LGBT families and visitors, with children and puppies often playing in the sand and plenty of community activities for all your family members.

Additional Resources:
Real Estate
Long Island Ferries
Jet Ski Rentals
Fire Island

Photo credit: Peter Dutton from Forest Hills, Queens, USA and Will Tung from Brooklyn, NY