For the past several summers, Bill and Hillary Clinton have done what New York City’s moneyed residents have done for decades: They spent their vacation amid the prime beachside real estate of Long Island.

In 2011 and 2012, there was the eight-bedroom, 12,000-square-foot East Hampton rental with a heated pool that the couple took for part of August, the kind of house that typically goes for $200,000 per month, according to local real estate listings.

Then, in 2013, they opted for an equally pricey six-bedroom mansion in Sagaponack with a private pathway to the beach. (Mrs. Clinton worked on her memoir, “Hard Choices,” from a sunny office with an ocean view.)

Last year, when speculation about Mrs. Clinton’s presidential run reached a fever pitch, the former first couple chose the comparatively lower-key town of Amagansett, just up Montauk Highway from the lobster shacks and fishermen at the end of Long Island. The seven-bedroom bluffside estate with sweeping views of Gardiners Bay, the kind of house in that area that rents for $100,000 for the month of August, was next door to the home of the Clinton friend and donor Harvey Weinstein.