Air Force One touched down shortly before midnight local time. The president headed to the rented oceanfront home in Kailua Bay where his wife, Michelle, daughters Malia and Sasha, and dog Bo have been vacationing since Saturday.
The president had planned to arrive Saturday, too, but pushed back his departure to stay in Washington while lawmakers wrapped up a frenzied and productive lame-duck session.
He begins his vacation on a high note, having secured victories on a nuclear arms treaty with Russia and the . He also struck a deal with Republican lawmakers , a compromise that angered some liberals but won Mr. Obama rare support from the GOP.
Before taking off for Hawaii, the president held a press conference that sounded much like a victory lap, reports CBS News correspondent Chip Reid.
Mr. Obama said the accomplishments of a postelection session of Congress demonstrateHe described the six-week lame duck session as "a season of progress for the American people."
The waning weeks of 2010 provided the president a much-needed boost following a volatile year and a self-proclaimed "shellacking" in the November midterm elections. Awaiting Mr. Obama come January is an economy still struggling to achieve steady growth, a Congress more heavily laden with Republicans and a host of GOP challengers poised to run for his job in 2012.
"[It's] extraordinary to have this kind of lame-duck session after this extraordinary midterm where Democrats lost the most seats either party has lost in any midterm since 1938," Ron Brownstein, editorial director of the National Journal Group, told CBS' "The Early Show".
"The president showed more nimbleness and more … ability to roll with the punch than we have seen at other points in his. He is resilient, he is persistent. After Scott Brown was elected last January, people said health care was doomed and of course they found their footing and were able to get it passed. What he showed here was more flexibility in being able to bring in Republicans."
With that in mind, the White House says the president is looking forward to spending a few days outside the glare of the Washington spotlight.
"He is as much as anything anxious to spend time where he grew up with his family and to see his sister," White House press secretary Robert Gibbs said.
Mr. Obama's half-sister, Maya Soetoro-Ng, and her family also live on Oahu. The president plans to visit with several childhood friends while on the island as well, Gibbs said.
Christmas in Hawaii has become a family tradition for the Obamas, who are spending their third straight year in Kailua. Mr. Obama also was forced to delay his departure last December due to action on Capitol Hill, where lawmakers worked until Christmas Eve to pass his signature health care overhaul legislation.
At the time, Obama spokesman Bill Burton told reporters traveling to Hawaii with Mr. Obama that the president's Christmas wish for the press corps was to "relax and to not anticipate any public announcements or news-making events."
It wasn't meant to be. On Christmas Day, a 23-year-old Nigerian man allegedly attempted to blow up a jetliner bound for Detroit. The incident consumed Mr. Obama's vacation, with the president receiving thrice-daily updates from the White House Situation Room and national security staffers briefing reporters, often at a moment's notice.
Administration officials will be prepared for any similar surprises this year. A small team of White House advisers, including Burton, deputy chief of staff Jim Messina and deputy national security adviser Ben Rhodes, are traveling with the president, who will receive daily briefings.
But unless outside events interfere, there will be little else on the president's schedule. As in past years, the president and first lady are likely to start their day with a morning workout at a gym at Marine Corps Base Hawaii. Mr. Obama has said he loves a secluded beach at the base and intends to "hit a couple of golf courses" while on the island.
Still, locals are likely to catch a few glimpses of the president during outings around town. Mr. Obama and his daughters have been regular visitors to Island Snow, a beachwear store famous for its shave ice - a version of what mainlanders know as snow cones.
If there's anything threatening to intrude on Mr. Obama's vacation plans, it could be Mother Nature. Oahu has been pounded with rain throughout the week, and more showers are forecast for the days ahead.