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Plantation Estates is an exclusive and gated Hawaii estate. It is located on Kailua Beach. The estate contains lush landscaping and ocean and garden lanais. The home where the Obamas stay is a 4,951 square foot residence containing five bedrooms, five bathrooms and a media room. There is an additional 1,945 square-foot covered lanai, and it’s near a U.S. Marine base where the president exercises when he stays there. The ocean-bay view is spectacular, and the home’s courtyard has a lagoon-style pool with a waterfall and island spa.
The Obamas used the home not only as a summer escape, but also as a winter getaway. They stayed there for their winter holidays from 2008 to 2012. They were almost always guaranteed good weather there. Pacific trade winds keep the temperature in the 70s and 80s all year. There are 40 public and private golf courses within easy-driving distance of Plantation Estates. Plantation Estates’ website makes this boast: “Kailua’s breathtaking beauty alone is believed to have inspired the famous Hawaiian farewell song Aloha Òe.”
From August 8-14, 2008 the Obamas visited Kailua during the 2008 U.S. Presidential Election, but they stayed at a different house belonging to Jill Tate Higgins, the general partner of Lakeside Enterprises, a Burbank, California private family investment company. During the visit he made what would be his last visit with his grandmother Madelyn Dunham who had raised him in Honolulu from age 10 on. She died on November 2, 2008, just two days before her grandson was elected President.
Obama returned to the area from December 20-31, 2008, when he made his first visit to Plantation Estate for a two-week vacation after winning the election. Among the activities was the scattering of his grandmother's ashes at Lanai Lookout at the same location where he had scattered his mother Stanley Ann Dunham's ashes in 1995.
Obama returned the following year from December 24, 2009-January 3, 2010. He stayed at Plantation Estates foe that trip. During the visit he went to his maternal grandfather Stanley Armour Dunham's grave at National Memorial Cemetery of the Pacific. Obama's trip was cut short after he had to address the the attempted Christmas bombing of Northwest Flight 253.
Obama was back for the next Christmas season from December 23, 2010-January 3, 2011. The visit was planbed to be 11 days, but he arrived day later than planned because he was awaiting Congressional approval of the New START treaty. First Lady Michelle Obama, first daughters Malia Obama and Sasha Obama and first dog Bo arrived earlier on December 18 flying on a C-40B Special Mission Aircraft. The Obamas were criticized because of press reports which indicated that the family not flying with the President cost the taxpayer an extra $63,000 to $100,000. Obama postponed his departure date one day to January 4. During the vacation he made a number of recess appointments. During the trip Hawaii Governor Neil Abercrombie who knew Obama and his family as a child, made arrangements to release the President's original birth certificate showing that Obama was born in Hawaii and not in Kenya as so-called "birthers" claimed. On the trip Obama dined with his half sister Maya Soetoro-Ng at Alan Wong's Restaurant near his boyhood home in Honolulu. He also went snorkeling with his family at Hanauma Bay on a Tuesday when the bay is normally closed to tourists. On the trip Obama was reported to have read The Thousand Autumns of Jacob de Zoet by David Mitchell (author), Our Kind of Traitor by John le Carré and President Reagan: The Role of a Lifetime by Lou Cannon.
The following winter, Obama and his family arrived on December 23, 2011 and stayed until January 1, 2012. He visited once again on December 21, 2012.
This year the Obamas once again plan to return to Hawaii. Their proposed itinerary from December 18, 2015 to January 2, 2016 can be found here.