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, prompting the toys to come to their rescue by digging them out and releasing them from a block of ice.
- Tom Hanks: Woody
- Michael Keaton: Ken
- Jodi Benson: Barbie
- 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
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.
- This is the first Toy Story production to be set after the events of Toy Story 3.
- This is also 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 as in a few seconds, we see Buzz speaking Spanish.
- When Buzz mispronounces "Hawaii" and Woody corrects him, they re-create the scene in Toy Story 2 where Buzz mispronounces "s'mores" and Woody corrects him.
- It can be assumed that Bonnie's family has a pet cat as Buzz mentioned (in Spanish) that he and the other toys removed the poop from the kitty litter.
- 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 it on the right side of your head signifies that the wearer is single.
- Wearing it on the left signifies that the wearer is either married or at least has a boyfriend (or girlfriend if the wearer is a boy).
- 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 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 symbolizes respect, appreciation, enlightenment, protection and peace. This could imply Buzz's new role of protecting Jessie.
- Hamm makes a comment that he had an uncle that was a pilot. This could be a reference to the 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.
- This is the only Toy Story Toons short to not be made by Pixar Canada.
- This is so far the only episode to feature Barbie, Ken, Chuckles and Peas-in-a-Pod, and have Dolly, Buttercup, Slinky and the Aliens speaking with the former first two as of now having the film rights owned by Sony.
- Hawaii's state fish, the Humuhumunukunukuapua'a, is a possible reference to a deleted song from High School Musical 2.
- Cars 2 DVD, Blu-ray combo pack and Blu-ray 3D combo pack released November 1, 2011
- Pixar Short Films Collection Volume 2 DVD and Blu-ray released November 13, 2012 with Small Fry.
- Toy Story of Terror! DVD and Blu-ray released August 19, 2014 with Small Fry and Partysaurus Rex.