The summer rental market in the Hamptons has changed a lot over the past 10 years. There’s more availability than ever, courtesy of online home-sharing sites, though real estate agents say that areas such as East Hampton and Southampton still have limited offerings. Then, too, some communities have tightened the rules for short-term rentals, and while that hasn’t slaked the demand for high-end vacations, it’s made finding a luxury home share complicated.
To help, we’ve done some of the legwork, rounding up five private homes available on the short-term home-rental website Airbnb, with amenities ranging from heated pools to fanciful architectural details. So find your favorite bathing suit and pack a bag. Summer is waiting.
East Hampton Village: Starting at $2,000 a night
Built in 2003, this four-bedroom, 5 1⁄2-bath home features a heated pool (open through early October) and an indoor fireplace, plus two private parking spaces.
The main draw of the property is its location, which is in the center of East Hampton Village, with stores and restaurants 100 yards away. All the village beaches are within 2.2 miles (one is as close as 1.3 miles away), and the train is 0.4 miles away (an estimated 9-minute walk).
Owners Robert and Michelle Kinney, who own an international legal recruiting firm, have been Airbnb hosts since 2012. Michelle says the location makes it the perfect vacation spot. “When looking for a second home, or any home for that matter, we always focused on location,” she says. “For us, a good location is being as close to the action as possible while still maintaining privacy.”
Montauk: Starting at $1,150 a night
Nestled in the hills of Montauk, the five-bedroom, 3 1⁄2-bath Tower House is designed to bring together indoor and outdoor living. Close to the beach and a 10-minute walk from downtown, the house is full of windows, skylights and glass doors. The deck has a grill for outdoor cooking. Inside, the kitchen is equipped with a custom-made hardwood table that seats eight, plus enough serving ware to accommodate 16. The home’s signature tower provides space for napping or reading. “Not many houses have a tower, so my house is very unique in that regard,” says owner Charles Whalen, who’s been an Airbnb host for a year.
Whalen, whose brother John was the architect, says the location reminds him of his childhood family vacations with their other brother Robert. The brothers, who are triplets, grew up in the Bronx but spent many summers in the area. “I love hosting families because of the experience of meeting new people and allowing kids to enjoy the Montauk experience like I did when I was a kid,” Whalen says.
Westhampton: Starting at $1,250 a night
You may not be able to sleep on the beach, but this five-bedroom, 4 1⁄2-bath, three-story house across the street from the ocean is the next best thing. The newly constructed home was designed to take the best possible advantage of its narrow 50-foot lot size, squeezing in amenities such as an indoor fireplace, a pool and free parking, plus a spa bathroom with a steam room.
Owner Fran Moss, who has been hosting with Airbnb four years, says she loves the expansive sense of nature that sweeping views provide. “The land to my west is parkland, and to the east, it’s protected open views, which create a dramatic sense of privacy and space,” she says.
Owner Moss says the house is also for sale for $2.65 million, and fetches as much as $100,000 as a seasonal rental.
East Quogue: Starting at $1,500 a night
This seven-bedroom, 6 1⁄2-bath rental is designed for poolside lounging.
The 1-acre property features an outdoor hot tub, a rock waterfall and a pool. The home has a fireplace and a game room, and there’s parking.
Owner Matteo Patisso, of Hamptons Luxury Rentals, has been hosting with Airbnb for four years and finds he enjoys the social aspect of using Airbnb. “We meet great people who are having the vacation of a lifetime,” he says.
Southampton: Starting at $2,500 a night
Close to the Village of Southampton, this six-bedroom, five-bath home was custom built in 2010 by owner Gary Flanagan, who owns a construction company.
The property’s backyard features a heated pool and hot tub and an outdoor cooking area with a grill. Also on the property is a separate guesthouse with its own bedroom, kitchen and bathroom.
“I started building this in 2007 as a large weekend project,” says Flanagan, who has been hosting with Airbnb since 2015. After a few years trying to get the details (and all the local permits) right, he finally found himself with a place to call home, which he also loves renting out. “I jumped through some hurdles, but in the end I got a home and a Hamptons experience.”