The family arrived on Aug 23 after a four-hour delay in Washington to avoid Hurricane Bill, and as they drove to their vacation home, they were greeted along the way by dozens of waving and cheering supporters, who carried signs reading 'Aloha Obama Family' and 'Hope, Obama'.
Senior adviser Valerie Jarrett, who owns a house on the island, joined the first family, and Obama's half-sister Maya Soetoro-Ng was also with them.
Also travelling with the Obamas was their first dog Bo, who made an unscheduled appearance in the press cabin aboard Air Force One before being retrieved by Malia Obama.
Obama, through spokesman Bill Burton, said that there were no plans to visit ailing Sen. Ted Kennedy, and also dismissed speculation that the President might play golf with Tiger Woods as a 'bad rumour'.
Burton also said that the President asked that the press "respect the privacy of the girls while they are out here on vacation".
Burton also delivered "specific instructions from the president for the press corps" in a gaggle aboard Air Force One.
"He wants you to relax," Polictico.com quoted Burton as saying.
"Have a good time, take some walks on the beaches. Nobody's looking to make any news," he added.