The Caldwell family embarks on a vacation to Puerto Rico, where the father is also involved in a covert business negotiation, while the children explore their own interests. It’s been eight years since the events of “Au Pair,” and Alexander Caldwell, now a high school valedictorian, joins his sister Katie, a college freshman, and her roommate Ariana for a summer getaway with their father Oliver and stepmother Jenny. Their current nanny opts out of the trip, leaving the busy parents to care for their newborn, Sarah, in Puerto Rico. Meanwhile, the young CFO, Walter Hausen, is plotting a takeover of Oliver’s company, CCI Tekhausen, which was established in “Au Pair II.” Oliver and Jenny must navigate the challenges of connecting with their children across generational divides, new career aspirations, and the romantic escapades of their once mischievous kids.