Dynamic Watchlist Hub: Apr 17, 2026

10 Best Movies Like Holiday for Bill

If you loved Holiday for Bill, 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 Holiday for Bill.

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#1
Boot Camp

Boot Camp

2024★ 6.4

Why watch this? A perfect follow-up to Holiday for Bill for fans of Romance. It captures a similar light-hearted atmosphere.

Unathletic Whitney Carmichael signs up for an intense summer boot camp to reinvent herself and falls for her personal trainer. She then finds the strength to embrace her true self ...

#2
A California Christmas

A California Christmas

2020★ 6.4

Why watch this? A perfect follow-up to Holiday for Bill for fans of Romance. It captures a similar light-hearted atmosphere.

With his carefree lifestyle on the line, a wealthy charmer poses as a ranch hand to get a hardworking farmer to sell her family’s land before Christmas....

#3
The Matchmaker's Playbook

The Matchmaker's Playbook

2018★ 7.2

Why watch this? A perfect follow-up to Holiday for Bill for fans of Romance. It captures a similar heartwarming atmosphere.

After a career-ending accident, former NFL recruit Ian Hunter is back on campus, and he's putting his extensive skills with women to work as one of the masterminds behind a success...

#4
Love in Taipei

Love in Taipei

2023★ 6.7

Why watch this? A perfect follow-up to Holiday for Bill for fans of Romance. It captures a similar light-hearted atmosphere.

A young American woman is sent by her parents to a cultural immersion program in Taipei where she begins a new journey of self-discovery and romance....

#5
Players

Players

2024★ 6.1

Why watch this? A perfect follow-up to Holiday for Bill for fans of Romance. It captures a similar light-hearted atmosphere.

New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it take...

#6
Hello, Goodbye, and Everything in Between

Hello, Goodbye, and Everything in Between

2022★ 6.2

Why watch this? A perfect follow-up to Holiday for Bill for fans of Romance. It captures a similar emotionally gripping atmosphere.

Clare and Aidan make a pact to break up before college — no regrets, no broken hearts. But will one epic goodbye date offer them a last chance at love?...

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