Barack, 54, along with First Lady Michelle and daughter Sasha (and dogs Bo and Sunny), departed from the White House at about 4:35 p.m. Friday, landing on the island almost exactly two hours later.
Their trip was actually ahead of schedule: The Obamas had originally planned to begin vacationing on Saturday, Press Sectary Josh Earnest said. But, as they did last year, the family decided to start things early.
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And like last year, the Obamas returned to the same seven-bedroom, nine-bath, 8,000 square-foot rental home in the Chilmark neighborhood, which also reportedly has a basketball court and an infinity pool.
It's the president's sixth Martha's Vineyard vacation since assuming office and the vacation is expected to include plenty of bike rides, beach trips and golf.
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As he told reporters Friday afternoon, in the middle of signing a bill, "I know you'll miss me."
One person the family may cross paths with while away? Former Secretary of State, and presidential front-runner, Hillary Clinton.
They are both expected to attend a birthday party for Ann Jordan, the wife of Democratic adviser Vernon Jordan.
Reporting by SANDRA SOBIERAJ WESTFALL