On an episode of The Tonight Show with Jay Leno (1992), Dustin Hoffman said that his cameo in the film was unplanned and not scripted. He was driving by the Blockbuster shown in the film and saw all of the cameras and equipment so he decided to stop in and see what was happening. Because he knew director Nancy Meyers, they worked up a scene which ultimately made the final cut.
Iris's tiny cottage is contrasted to Amanda's stunning house but in reality thanks to UK property prices an unspoiled cottage like that in a good location could easily be worth a million pounds, not far off two million dollars. She's far from slumming it, no matter how basic the kitchen.
Within Hollywood, director Nancy Meyers is known for doing a rather large number of re-takes for any given scene segment. And during the shooting for The Holiday, at the end of a large number of re-takes for one particular segment of the newspaper Christmas party scene, lead actress Kate Winslet aroused a good-natured laugh from everyone on set when, after the end of what she felt was a particularly good take following another long series of takes, she dropped to her knees in front of a table, clasped her hands together on the tabletop, and began to pantomime a prayer for that to be the last take of the segment.
Director Nancy Meyers states in the commentary that she bases elements in her movies off of real life events that she's experienced, for example the esophageal spasms that Cameron Diaz's character has, which is something Meyers used to experience herself.
Several references to Ennio Morricone: The movie's main theme starts with the same five chords as "Deborah's theme" from Once Upon a Time in America (1984), Miles urges Iris to rent The Mission (1986) because of its score, and the main theme of Cinema Paradiso (1988) plays on Miles' car stereo the first time he and Iris meet (he even tells her that it was composed by Ennio Morricone). Also, Eli Wallach was in The Good, The Bad and The Ugly, one of the most famous films Morricone composed for.
Upon arriving at Amanda's Los Angeles home, she runs around excitedly and eventually finds a wall of DVD cases. She scans through them and selects one. Pulling one the shelf and opening it, she's interrupted by Jack Black's character at the gate. The movie Iris selected was Punch-Drunk Love (2002).
There is a scene in the film in which Cameron Diaz and Jude Law are chasing one another in a field after having lunch, which features a bossa nova-style piece from the musical score. Director Nancy Meyers was so intent on having this scene in the film as a tribute to similar scenes featured in the films of Rock Hudson and Doris Day. Meyers was so intent on having the right music for the scene, that the score's composer, Hans Zimmer, actually named the piece "For Nancy."
Reportedly, the three members of British indie rock band The Wombats went to see this movie, expecting a rom-com in the spirit of Bridget Jones's Diary (2001). They ended up hating the film so much, that they wrote the song 'Kill the Director' about it, which contains lyrics like "If this is a rom-com, kill the director" and "This is no Bridget Jones!"
Rufus Sewell who plays "Jasper" is connected to Venice in another movie. The movie Dangerous Beauty is set in Venice and in this movie his character Jasper asks Iris if she wants to sneak away to Venice when she gets back to London.