Skeeter Bronson (ADAM SANDLER) has lived his entire life at the Sunny Vista Hotel, first as a kid with his sister when their dad ran the place, and now for the past 25 years serving as the handyman for owner Barry Nottingham (RICHARD GRIFFITHS). Despite being quite good at his job, the likes of manager Kendall Duncan (GUY PEARCE) and front desk attendant Aspen (LUCY LAWLESS) look down on him, while Nottingham's high society daughter, Violet (TERESA PALMER), doesn't give him much notice. Accordingly, that only adds to his disappointment when Mr. Nottingham announces that Kendall, rather than Skeeter, will be the general manager of their newest, but yet-to-be-built property.
At the same time, Skeeter ends up having to watch his young niece, Bobbi (LAURA ANN KESLING), and nephew, Patrick (JONATHAN MORGAN HEIT), when their divorced school principal mom, Wendy (COURTNEY COX), has to go out of town to look for a new job, what with her school scheduled to be shuttered. Besides somewhat spacey hotel waiter Mickey (RUSSELL BRAND) helping him watch the kids, Skeeter also gets assistance from Wendy's friend, teacher Jill Hastings (KERI RUSSELL). Even so, it's up to Skeeter to tell the kids their bedtime stories, and since he has no experience with that, he comes up with some unorthodox tales, with his young charges throwing in various details.
To his surprise, some of the latter then end up actually happening in real life. And since Mr. Nottingham has changed his mind and will allow Skeeter to compete against Kendall for the new position, the handyman figures he can use those bedtime stories to ensure that he gets the job. Yet, as he starts to fall for Jill, he soon learns that his best laid plans don't always work out the way he, and the kids, have imagined.