Movies like Cinderella in the Caribbean (2023)
The best movies like Cinderella in the Caribbean (2023) are My Christmas Prince (2017), Picture a Perfect Christmas (2019) and Jingle Bell Princess (2021). If Cinderella in the Caribbean hooked you with its tv movie and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedPurple Hearts (2022)8.0/10 from 2,979 votes
- NewestMadea's Destination Wedding (2025)Released 2025
My Christmas Prince (2017)
Samantha, a dedicated teacher in Manhattan, returns to her home town of Maple Falls, Wyoming every year for Christmas. This year, she’s delighted when her boyfriend Alex, a European diplomat from the tiny country of Madelvia, decides to joins her. Samantha later discovers Alex is actually a prince destined for the throne, turning her entire world upside down. Realizing that staying with Alex means spending her life in the constant glare of publicity and giving up the job opportunity of a lifetime, Samantha must decide if she loves Alex enough to make the transition from teacher to royal – or will it be too big a leap
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisPicture a Perfect Christmas (2019)
An extreme-sports photographer returns home for the holiday to take care of her grandmother, only to have a neighbor grab her attention as he needs assistance watching his young nephew.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisJingle Bell Princess (2021)
An actual princess has some mechanical issues and is temporarily grounded. Does she have time for a lobster roll? It is Christmas time in Maine which means snow, quaint scenery, and lots of Christmas lights near the ocean. With the crew distracted attending to the repair, Princess Amelia deplanes to walk through a magical Christmas tree lot near the airport perimeter.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisGrace (2018)
A famous writer begins suffering from a crippling case of writer's block. His agent sends him a strange, belligerent woman to be his new assistant, hoping the change will inspire him.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisThe Nine Kittens of Christmas (2021)
Cat lovers Zachary and Marilee are thrown back together at Christmas when they're tasked with finding homes for a litter of adorable kittens.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisFather of the Bride (2022)
A father comes to grips with his daughter’s upcoming wedding through the prism of multiple relationships within a big, sprawling Cuban-American family.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Enchanted Christmas Cake (2021)
Gwen recently lose her grandmother and she is struggling to run their bakery and regain the Christmas spirit, and figure out her grandmother's magical recipe for the town's legendary Enchanted Christmas Cake.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisFour Christmases and a Wedding (2017)
When event planner Chloe is hired to plan the local Christmas Festival, she is beyond thrilled to embrace the challenge. Professionally, everything is going great, but much to the dismay of her mother, Chloe confesses she has given up on ever finding Mr. Right. That all changes the night of the opening of the festival when she meets Evan. The two begin a whirlwind romance, but as Christmas Day nears, Chloe learns that Evan is being transferred overseas for work. What follows is three more Christmases where Chloe and Evan cross paths at the annual festival, but each year something - or someone - stands in the way of true love. Will a touch of Santa's magic on their fourth Christmas Eve finally bring them together?
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisChéri (2009)
The son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisMuch Ado About Nothing (1993)
In this Shakespearean farce, Hero and her groom-to-be, Claudio, team up with Claudio's commanding officer, Don Pedro, the week before their wedding to hatch a matchmaking scheme. Their targets are sharp-witted duo Benedick and Beatrice -- a tough task indeed, considering their corresponding distaste for love and each other. Meanwhile, meddling Don John plots to ruin the wedding.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisBefore We Go (2014)
A chance encounter between two strangers in Grand Central Terminal sparks a life-changing, nighttime sojourn through New York City. They grow into each other's most trusted confidants when an evening of unexpected adventure forces them to confront their fears and take control of their lives.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisPlaying by Heart (1998)
In a vibrant tapestry of love and longing, nine interconnected souls navigate romance and heartbreak in L.A., where passions collide and truths unfold, revealing that the heart's desires often lead us where we least expect.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisA California Christmas: City Lights (2021)
Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisPaper Heart (2009)
Paper Heart follows Nick and Charlyne on a cross-country journey to document what exactly "love" is. Interviewing ministers, happily married couples, chemists, romance novelists, divorce lawyers, a group of children and more, the determined young girl attempts to find definition and perhaps even experience the mysterious emotion.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisMadea's Destination Wedding (2025)
Madea packs her best floral dresses and a whole lot of chaos when the Simmons family heads to the Bahamas for her grandniece's whirlwind wedding.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisSaving Silverman (2001)
A pair of buddies conspire to save their best friend from marrying the wrong woman, a cold-hearted beauty who snatches him from them and breaks up their Neil Diamond cover band.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisValentine's Day (2010)
Intertwining couples and singles in Los Angeles break-up and make-up based on the pressures and expectations of Valentine's Day.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisPurple Hearts (2022)
An aspiring musician agrees to a marriage of convenience with a soon-to-deploy Marine, but a tragedy soon turns their fake relationship all too real.
Why it matches: Recommended by TMDB viewers · both romance & drama
Absolute CinemaMovies like thisLittle Manhattan (2005)
Ten-year-old Gabe Burton is just an average kid growing up in Manhattan until Rosemary Telesco walks into his karate class. But before Gabe can tell Rosemary how he feels, she reveals that she won't be going to public school any more. Gabe has a lot more to learn about life, love, and girls.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisLast Chance Harvey (2008)
In London for his daughter's wedding, a struggling jingle-writer, Harvey Shine, misses his plane to New York, and thus loses his job. While drowning his sorrows in the airport pub, Harvey meets Kate, a British government worker stuck in an endless cycle of work, phone calls from her mother, and blind dates. A connection forms between the unhappy pair, who soon find themselves falling in love.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisThe Guru (2002)
Bored with Bollywood movies but fascinated with their Hollywood counterparts from his youth, Ram dreams to become a singer and actor in America, the country where dreams are made. He is encouraged when his American-based close friend, Vijay Rao, comes for visit, and brags about driving a Mercedes and living in a penthouse.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisAll Aboard for Love (2023)
As Alison prepares for new ocean adventures, business executive Joel navigates his way into her heart and they become co-captains for life.
Why it matches: Similar story and style · both comedy & romance
Monsoon Wedding (2001)
A stressed father, a bride-to-be with a secret, a smitten event planner, and relatives from around the world create much ado about the preparations for an arranged marriage in India.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisThe Party 2 (1982)
After moving to a new city, a young French teenage girl falls in love with a boy and thinks of having sex with him, since her girl friends have already done it.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisThe Heartbreak Kid (2007)
Eddie, the 40-year-old confirmed bachelor finally says "I do" to the beautiful and sexy Lila. But during their honeymoon in Mexico, the woman of his dreams turns out to be a total nightmare, and the guy who could never pull the trigger realizes he’s jumped the gun.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisCoast to Coast (2004)
Barnaby and Maxine Pierce, an embattled married couple in Connecticut, are on the verge of divorce. Their son is getting married in California and they decide to drive across the country to attend. Along the way, as they visit family and friends, they reflect on their tattered relationship and the events that transpired to create the estrangement.
Why it matches: Similar story and style · both drama
My Best Friend's Wedding (1997)
When she receives word that her longtime platonic pal Michael O'Neal is getting married to debutante Kimberly Wallace, food critic Julianne Potter realizes her true feelings for Michael -- and sets out to sabotage the wedding.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisWhat Happens in Vegas (2008)
During a wild vacation in Las Vegas, career woman Joy McNally and playboy Jack Fuller come to the sober realization that they have married each other after a night of drunken abandon. They are then compelled, for legal reasons, to live life as a couple for a limited period of time. At stake is a large amount of money.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisThe Wedding Party (2016)
Filmed in one continuous 119-minute shot, THE WEDDING PARTY tells the story of a groomsman who must navigate a slew of disasters and maintain order at his best friend's wedding reception.
Why it matches: Similar story and style · both romance & comedy
The Shell Seekers (2007)
Penelope Keeling, a sixty-four-year-old daughter of a famous artist, reflects on her life, and the fate and choices that defined it, when she arrives in the Mediterranean to stay with her headstrong daughter. Shifting through time, and falling into place like the pieces of a jigsaw, the truth of Penelope's rich, heartbreaking and surprising life unfolds.
Why it matches: Similar story and style · both drama & romance
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Frequently asked questions
What are the best movies like Cinderella in the Caribbean?
The closest matches to Cinderella in the Caribbean are My Christmas Prince (2017), Picture a Perfect Christmas (2019) and Jingle Bell Princess (2021). Below are 27 more, each with the reason it matches.
What should I watch after Cinderella in the Caribbean?
Start with My Christmas Prince (2017), the closest match to Cinderella in the Caribbean.
What is the highest-rated movie like Cinderella in the Caribbean?
Purple Hearts (2022), rated 8.0/10 by 2,979 TMDB users.
What is the newest movie like Cinderella in the Caribbean?
Madea's Destination Wedding (2025) is the most recent release on this list.
Are there English movies like Cinderella in the Caribbean?
Yes: My Christmas Prince (2017), Picture a Perfect Christmas (2019) and Jingle Bell Princess (2021).
How are movies similar to Cinderella in the Caribbean chosen?
First come films that Trakt’s viewers watch alongside Cinderella in the Caribbean, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.