Popsugar Celebrity Celebrity Families Obama Family Vacation Pictures 33 Times the Obamas Bonded During Their Family Vacations August 24, 2016 by Kelsie Gibson View On One Page Photo 30 of 33 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 30 The whole family walked across the South Lawn of the White House on Dec. 24, 2009 to jet off to Hawaii for Christmas and New Year's Day. Previous Next Start Slideshow Michelle ObamaBarack ObamaCelebrity FamiliesCelebrity KidsCelebrity VacationsSasha ObamaMalia Obama