The Caldwells take a family trip to Puerto Rico where their father is also securing a secret business deal, while the kids find their own paths. Eight years have passed since the events of Au Pair, and newly graduated as his high school's valedictorian, Alexander Caldwell joins his visiting sister, college freshman Katie and her roommate Ariana on a family summer vacation with father Oliver and stepmother Jenny. Oliver and Jenny's current nanny declines to join them and the over-worked parents/executives must take care of their newborn baby Sarah in Puerto Rico. Amidst corporate scheming by the young company CFO Walter Hausen, who is planning a takeover of Oliver's company CCI Tekhausen (formed in Au Pair II), Oliver and Jenny must contend with bridging the generation gap with the family, new career motivations and the romances of their 'newly reformed' prankster kids.
Andy "Brink" Brinker and his in-line skating crew--Peter, Jordy, and Gabriella--who call themselves "Soul-Skaters" (which means they skate for the fun of it, and not for the money), clash with a group of sponsored skaters, Team X-Bladz--led by Val--with whom they attend high school in southern California. When Brink discovers his family is in financial trouble, he goes against the wishes of his parents and his friends and joins Team X-Bladz. Brink tries to lead a double life but will be able to pull it off?
When Marty DePolo dies after eating a six-month-old hamburger, he is chosen to be his best friend's guardian angel.
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