If you're flying into the Oakland Airport, why not add a connector flight to John Wayne Airport (Orange County) which is the closest to Disneyland, LAX, Long Beach, Ontario or Burbank because it doesn't sound like you're planning a sightseeing drive from Oakland to Disneyland. If you need a car once in SoCal you can rent one at whichever airport you fly into.
The fastest driving route from Oakland to Disneyland is via I-5, but there is nothing scenic about it. Bakersfield is about 4 hours from Oakland, but you will be running into East Bay commute traffic when arriving at 5 PM.
If you take 99, Fresno is about 3 hours from Oakland, but from there it will take another 4 hours to Anaheim.
If you stop overnight on the way, you will have to factor in heavy traffic in LA the next morning. If you're going to arrive in Oakland at 5 PM, have dinner first, then head down to Anaheim after commute traffic lightens up. If you leave around 7 you'll probably get to Anaheim around 1:30 AM.