"Pee-wee's Big Holiday" received positive reviews from critics. On Rotten Tomatoes, the film got an 82% approval rating. 44 reviews gave it an average rating of 6.9/10. The site's said, "The simple story is a little short on laughs, but there's plenty of sweet wackiness for Pee-wee Herman fans to enjoy". On Metacritic, the film scorde 63 out of 100, from 19 critics, indicating "generally favorable reviews".