Dynamic Watchlist Hub: May 14, 2026

10 Best Movies Like How to Take a Vacation

If you loved How to Take a Vacation, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

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Expert Review & Ratings

See our full critical analysis and audience score for How to Take a Vacation.

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#1
Me Time

Me Time

2022★ 5.9

Why watch this? A perfect follow-up to How to Take a Vacation for fans of Comedy. It captures a similar light-hearted atmosphere.

With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure....

#2
What We Did on Our Holiday

What We Did on Our Holiday

2014★ 6.7

Why watch this? A perfect follow-up to How to Take a Vacation for fans of Comedy. It captures a similar light-hearted atmosphere.

Doug and Abi and their three children travel to the Scottish Highlands for Doug's father Gordie's birthday party. It's soon clear that when it comes to keeping a secret under wrap...

#3
Held Up

Held Up

1999★ 5.8

Why watch this? A perfect follow-up to How to Take a Vacation for fans of Comedy. It captures a similar light-hearted atmosphere.

What should have been a romantic getaway turns into one hilarious debacle after another when Michael's woman dumps him in the desert where he gets carjacked by a teenager and he is...

#4
Tommy Boy

Tommy Boy

1995★ 6.8

Why watch this? A perfect follow-up to How to Take a Vacation for fans of Comedy. It captures a similar light-hearted atmosphere.

To save the family business, two ne’er-do-well traveling salesmen hit the road with disastrously funny consequences....

#5
Dave Chappelle: The Closer

Dave Chappelle: The Closer

2021★ 7.2

Why watch this? A perfect follow-up to How to Take a Vacation for fans of Comedy. It captures a similar light-hearted atmosphere.

As he closes out his slate of comedy specials, Dave takes the stage to try and set the record straight — and get a few things off his chest....

#6
Chris Rock: Never Scared

Chris Rock: Never Scared

2004★ 7.5

Why watch this? A perfect follow-up to How to Take a Vacation for fans of Comedy. It captures a similar light-hearted atmosphere.

Chris Rock, the three-time Emmy Award-winner, comedian, actor, and host of HBO's acclaimed The Chris Show, stars in his fourth solo stand-up special for HBO, Chris Rock: Never Scar...

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