Air Force One touched down in Honolulu minutes after midnight local time on Saturday. The first family departed the plane and traveled quickly to their vacation house in the beach town of Kailua, a scenic, sleepy beach town on the east side of Oahu.
Kailua is roughly 12 miles from downtown Honolulu. Obama's vacation house sits near a Marine base, on the north end of a five-mile stretch of beach popular among windsurfers and paddle surfers.
As the president and his family departed Air Force One, Obama had shed the jacket he was wearing when he left Washington and was in a dress shirt with the sleeves rolled up. The first family left Washington on Friday night.
White House officials say the president's vacation itinerary doesn't include any scheduled public events.
No return date has been given by the White House. Obama himself said earlier Friday that, since a deal hasn't been reached to avert the so-called "fiscal cliff," he would be returning to Washington after Christmas.
Associated Press writer Oskar Garcia contributed to this report.