$100,000 and Up
Katama Point, Martha’s Vineyard
For those who want the beach and the mansion and don’t mind paying for both of them. There aren’t a lot of houses this size to rent on Martha’s Vineyard, and this one is bigger than most at this price point. There’s a master suite, a library, and a great room, as well as three themed guest rooms and a third-floor “nest” with a 360-degree view of Edgartown Harbor, Chappaquiddick Island, and the Atlantic Ocean. The white sands of South Beach are a fifteen-minute drive away, as is Bill Clinton’s favorite golf course, Farm Neck Club.
Nassau Point, Long Island
The most expensive rental in the North Fork this season is still a fraction of the price a property this impressive would fetch in the Hamptons. The three-bedroom main house, built in 1912 and renovated in the nineties, is located on four and a half acres on the tip of Nassau Point in Cutchogue, the most exclusive neighborhood in the area. “You see water from every single room,” says Corcoran broker Sheri Winter Clarry. Spend the mornings kayaking across placid Wunneweta Creek to reach your private beach, or sail your 50-footer on the Peconic in the afternoons.
Barcelona Point, Sag Harbor
Far, far from the madding crowd, this pricey but extremely tasteful four-bedroom contemporary house is nestled on the nub of Barcelona Point, a 342-acre reserve surrounded by salt marshes, egrets, and pebble beaches. That’s probably what attracted renters like Sarah Jessica Parker and Matthew Broderick, Edgar Bronfman Jr., and Jann Wenner. Owned by oil heiress Christophe de Menil, the house has a heated pool protected by low hedgerows. If you’re lonesome, amble a few miles along the beach to Sag Harbor and get a Bloody Mary at the American Hotel.
Bridge Lane, Bridgehampton
For the last two weeks of July, you too can live like a Goldman Sachs partner in this scorchingly expensive but achingly beautiful 20,000-square-foot oceanfront estate with two houses, a full gym in a separate building, a 60-foot heated gunite pool, and a tennis court. Two weeks is probably just enough time to count the thirteen bedrooms in total, multiple patios, decks, entertaining rooms, and French doors and balconies that overlook both the ocean and Sag Pond. (Don’t forget to bring the mosquito repellent.) Set out on a 33.7-acre parcel and reserve, this McMansion is one of the most visible houses in the Hamptons.