Months after Toy Story 3, it's winter time, and winter break for Bonnie, who is going on vacation to Hawaii with her mother for a week. The toys are excited to have a week of relaxation, but Barbie and Ken reveal themselves to have stowed away in Bonnie's backpack, hoping to join her in Hawaii. Bonnie leaves them in her room, however, much to Ken's horror when he realizes they are not going to Hawaii. Barbie reveals to Woody that Ken planned to have their first kiss on a beach at sunset (based off of a travel brochure for Hawaii), inspiring Woody, Buzz, and the rest of Bonnie's toys to go all out and recreate Hawaii for the two. After various "adventures" in Hawaii, Ken and Barbie share their first kiss in the snow at sunrise, recreating the scene from the brochure. However, the two end up being buried in snow when they step off the front porch, and the toys work to free them from a block of ice.
Most of the voice actors of the toys of Toy Story 3 returned in the short.
- Jodi Benson: Barbie
- Michael Keaton: Ken
- Tom Hanks: Woody
- Tim Allen: Buzz Lightyear
- Joan Cusack: Jessie
- Don Rickles: Mr. Potato Head
- Estelle Harris: Mrs. Potato Head
- Wallace Shawn: Rex
- John Ratzenberger: Hamm
- Blake Clark: Slinky Dog
- Jeff Pidgeon: Aliens
- Emily Hahn: Bonnie Anderson
- Lori Alan: Bonnie's Mom
- Timothy Dalton: Mr. Pricklepants
- Jeff Garlin: Buttercup
- Kristen Schaal: Trixie
- Bonnie Hunt: Dolly
- Bud Luckey: Chuckles
- Zoe Levin: Peas-in-a-Pod
- Angus MacLane: Captain Zip
Bullseye is a non-speaking character.
Hawaiian Vacation was first announced by Lee Unkrich in July 2010. As quoted: "We have announced we're going to do a short film in front of Cars 2 that uses the Toy Story characters. We're going to keep them alive; they're not going away forever."
In mid-December 2010, veteran Disney and Pixar animator Floyd Norman tweeted twice on Twitter about the short film saying, "Saw the Pixar Hawaii short. Cute." and "Ken and Barbie want to go to Hawaii. I don't know what it's gonna be attached to. Fun stuff, however."
On February 3, 2011, Tom Hanks recorded new dialogue for his character Woody, as seen in his tweet on Twitter: "3 directors boss "Woody" around for Toy Story shorts. Come on, guys!", meaning that he was recording for more than one episode.
- Hawaiian Vacation is the first Pixar short based on one of their movies to be released theatrically with their latest film rather than made for a DVD or Blu-ray release.
- This is also the first, and so far only, Pixar short to contain subtitles.
- It can be assumed that Bonnie's family has a pet cat as sand was emptied from a litter box that Buzz mentioned (in Spanish) they removed poop from.
- When Bonnie opens the door at the beginning, Trixie is slammed against the wall. When Bonnie closes the door, she ends up leaning against the wall, and falls down. This is the same action that happened to Rocky Gibraltar when Andy opens the door during his birthday party in the original Toy Story.
- Like some women in Hawaii, Jessie wears a flower on her head to let everyone know her relationship status. Wearing the flower on the left signals that the wearer is married or in a relationship. If it is worn on the right side, it means that the wearer is single. Jessie wears her flower on the left side of her head which shows in a subtle way that she and Buzz are in a relationship without having any love scenes between the two.
- The end of the first Toy Story film took place around winter time.
- Lei's colors also have different meanings, the pink lei that Jessie wears is one of three colors that usually symbolizes love.
- The Kukui lei that Buzz wears symbloizes respect, appreciation, enlightenment, protection and peace.
- Hamm makes a comment that he had an uncle that was a pilot, this could be a reference to the film Studio Ghibli film, Porco Rosso.
- This is the second time that live-action footage was used in a Pixar film, the first being WALL-E. This is the first short film to do so.