Movies Like Holiday in Handcuffs

If you liked Holiday in Handcuffs (2007), a comedy and romance movie directed by Ron Underwood, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Merry Christmas, Drake & Josh (2008)
★ 7.3/10Also comedy and family
Step brothers Drake and Josh must give a foster family the best Christmas ever or face years in jail for a Christmas party gone wrong.
2
'Twas the Text Before Christmas (2023)
★ 6.5/10Also romance and comedy
Addie is a New York City chiropractor mistakenly receives a text from “Nana.” The accidental text turns into a loving friendship between the matronly Nana and Addie who now communicate regularly. Nana invites Addie to…
3
A Christmas Prince: The Royal Baby (2019)
★ 6.3/10Also romance and family
Christmas brings the ultimate gift to Aldovia: a royal baby. But first, Queen Amber must help her family and kingdom by finding a missing peace treaty.
4
Candy Cane Lane (2023)
★ 6/10Also comedy and family
Determined to win the neighborhood's annual Christmas decorating contest, family man Chris makes a pact with an elf to help him out-do the competition. However, the elf casts a spell bringing the twelve days of…
5
The Princess Switch: Switched Again (2020)
★ 6.8/10Also family and romance
When Duchess Margaret unexpectedly inherits the throne & hits a rough patch with Kevin, it’s up to Stacy to save the day before a new lookalike — party girl Fiona — foils their plans.
6
Christmas on Windmill Way (2023)
★ 5.9/10Also romance and comedy
Mia Meijer gets ready for the Christmas Market Dutch Bake-Off and suspects that her grandmother, Ann, will walk away with the cherished Golden Rolling Pin thanks to her Kerststol, a traditional Dutch fruited Christmas…
7
A Christmas Miracle for Daisy (2021)
★ 5.9/10Also romance and comedy
Whitney Alder owns interior design firm Marietta Designs, which she runs with her friend Andi in the small town of Marietta, Montana. Whitney is designing Santa’s float for the annual Marietta Christmas Parade when a…
8
Beethoven's Christmas Adventure (2011)
★ 6/10Also family and comedy
A Christmas elf accidentally takes off in Santa's sleigh, crash lands in a small town, and loses the magic toy bag. Beethoven must rescue the elf, recover the bag from greedy crooks, and return the sleigh to Santa in…
9
Never Kiss a Man in a Christmas Sweater (2020)
★ 6.5/10Also romance and comedy
Single mom Maggie is facing Christmas alone until Lucas crashes into her life and becomes an unexpected house guest. Together they overcome Christmas while finding comfort in their growing bond.
10
12 Gifts of Christmas (2015)
★ 6.1/10Also family and tv movie
When Anna Parisi, an unemployed fine arts painter, is unable to make ends meet, she is hired to become a personal Christmas shopper for Marc, an uptight corporate exec. As they begin working together, Marc learns that…
11
Christmas in Evergreen: Letters to Santa (2018)
★ 6.8/10Also family and romance
Lisa's trip home to Evergreen for the holidays finds her shepherding an effort to save the town's beloved general store, fulfilling the wishes of a Christmas past and finding a romance full of Christmas magic.
12
Family Switch (2023)
★ 6.4/10Also comedy and family
When the Walker family members switch bodies with each other during a rare planetary alignment, their hilarious journey to find their way back to normal will bring them closer together than they ever thought possible.
13
EXmas (2023)
★ 6.4/10Also romance and comedy
When Graham decides to surprise his family by traveling home for Christmas, he is shocked to discover them already celebrating with an unexpected guest of honor, his ex-fiancée, Ali. The two exes battle it out to see…
14
Dolly Parton's Christmas on the Square (2020)
★ 5.9/10Also comedy and family
A rich and nasty woman returns to her hometown to evict everyone but discovers the true meaning of Christmas thanks to the local townsfolk – and an actual angel. Features 14 original songs with music and lyrics by…
15
Noelle (2019)
★ 6.6/10Also family and comedy
Kris Kringle's daughter, Noelle, sets off on a mission to find and bring back her brother, after he gets cold feet when it's his turn to take over as Santa.
16
To Grandmother's House We Go (1992)
★ 6.5/10Also family and comedy
When precocious twins Sarah and Julie feel like Mom is tired of them, they take off on an exciting adventure to their grandmother's house and encounter a pair of villains along the way.
17
Falling for Christmas (2022)
★ 6.2/10Also romance and comedy
An engaged, spoiled hotel heiress finds herself in the care of a handsome, blue-collar lodge owner and his precocious daughter after getting amnesia in a skiing accident.
18
A Christmas Story Christmas (2022)
★ 6.3/10Also comedy and family
Follows Ralphie, now adult, who returns to the house on Cleveland Street to give his kids a magical Christmas like the one he had as a child, reconnecting with childhood friends, and reconciling the passing of his Old…
19
Christmas at Grand Valley (2018)
★ 6.4/10Also tv movie and family
Burned out from the hubbub of the Chicago gallery world, artist Kelly returns home to the picturesque Grand Valley just in time for Christmas. Leo, businessman and all-star dad to his children, struggles to balance his…
20
Secret Summer (2016)
★ 6.7/10Also romance and family
Appraiser Rachel (Lindsey Shaw) receives the news that her top-notched client wants to buyout a small town’s beloved library to build a resort and spa on the land. Rachel is completely against the idea of leaving NYC…