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The Obamas’s first rental choice—where they stayed in 2009 and 2010—is impressive. The Plantation Estate, unofficially known as the “Winter White House”, opens up to a lagoon-style pool in the front courtyard with cascading waterfalls and a lavish heated spa. We imagine Barack and Michelle sipping piña coladas while Sasha and Malia splashed around in the heated pool.  Photo 2 of 10 in 10 Dream Modern Home Rentals In Hawaii