Inside Obama's Kailua Beach Vacation Homes

Landowners are being cagey this year about where Obama is staying on chic Hawaii beach.

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The Plantation Estate on Kailua Beach in Oahu, Hawaii.

With the fiscal cliff averted at last on New Year's Day, President Barack Obama returned to his vacation spot on Kailua Beach in Oahu, Hawaii Wednesday morning for some much-needed R & R. Obama had previously cut the vacation short to deal with the fiscal crisis.

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Each U.S. president has found his own way to unwind from the stresses of leading the free world, including Harry Truman, who once called the White House the "crown jewel of the federal penal system" because he felt so confined there. Ronald Reagan and George W. Bush both escaped to ranches out west.

But Obama prefers to spend the holidays at lavish rented estates in his former home state of Hawaii, where he plays golf, works out at the nearby Marine Corps base, and spends time with wife Michelle and daughters Sasha and Malia on the beach.

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The First Family rents a home each year on Paradise Point, a lush, green stretch of land in Kailua Beach, Oahu, that juts out over the ocean and contains an exclusive gated community.

From 2008 to 2010, that home was the "Plantation Estate," a lavish, 5,000-square-foot ocean-front home on Paradise Point described on its web site as "built for exceptional security, comfort and elegance just steps from the silky white sands of Kailua Beach." The home's security is due in no small part to its proximity to the Marine Corps Base Hawaii on Kaneohe Bay, which houses nearly 10,000 Marines, sailors and civilian employees.

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In 2011, the Obamas moved to a unnamed but similar vacation home down the street, which the Washington Post reported is 6,000-square-feet and contains an inner courtyard and expansive lawn that leads down to the beach.

This year, the Obamas are believed to be staying in the same unnamed home. But, which has been tracking the Obama's vacations since 2008, says that while it can "normally pinpoint" POTUS's Hawaii home, Kailua residents were "more cagey" about his whereabouts this year.

Glenn L. Weinberg, who owns Plantation Estate, did not respond to request for information from Whispers.

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The real estate website does know that the First Family remains on Paradise Point, however, where homes cost approximately $25,000 a week. The Obamas pay this fee out of their personal funds. But according to Keith Koffler at the White House Dossier blog, Obama's Hawaii vacation has cost taxpayers $7 million, due to the costs of flying Air Force One and an extensive security operation.

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  • Elizabeth Flock is a staff writer for U.S. News & World Report. You can follow her on Twitter or Facebook or reach her at

    Update, 01/04/12, 10:45 a.m.: Glenn Weinberg, who owns Plantation Estate, says the Obamas are not staying at his home this year because he rented it to another family.