Movies Like Caribbean Summer

If you liked Caribbean Summer (2022), a tv movie and romance movie directed by Steven R. Monroe, 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
As Luck Would Have It (2021)
★ 6.5/10Also tv movie and comedy
When Lindsey travels to Ireland to acquire land that is perfect for a resort, she decides to enter the town's matchmaking festival to prove her investment—and win over a handsome local.
2
A Prince in Paradise (2023)
★ 7.2/10Also tv movie and romance
Olivia, struggling with writer's block after a break up, takes a tropical holiday in hope of some inspiration and meets Prince Alexander, who needs some distance from his duty to marry royalty.
3
A Merry Christmas Wish (2022)
★ 5.9/10Also tv movie and comedy
Janie, a rising marketing executive living in The Big Apple, returns to her hometown of Woodland Falls when her Great-Uncle Randall passes away. Randall has even arranged for his farmhand, Dylan to help at the event…
4
Prom Pact (2023)
★ 7.2/10Also comedy and romance
It's prom season, and high school senior Mandy and her best friend and fellow outsider Ben are surrounded by over-the-top "promposals." Mandy is only focused on getting into her dream school Harvard, but as she starts…
5
Christmas at the Drive-In (2022)
★ 5.8/10Also tv movie and comedy
Sadie Walker is starting over in her hometown of Chesterfield, New York, following a series of major life disruptions that include leaving her law practice after losing her biggest case and no longer being engaged.
6
Marrying Mr. Darcy (2018)
★ 6.1/10Also tv movie and comedy
Schoolteacher Elizabeth Scott and businessman/philanthropist Donovan Darcy are blissfully in love and newly engaged. As the weeks fly by and the arrangements for their small autumn wedding grow more elaborate and…
7
Love on Harbor Island (2020)
★ 6.2/10Also romance and tv movie
Interior designer Lily returns home to help her Aunt Maggie run her marina-side bed and breakfast when she meets Marcus, a handsome seaplane pilot whose work delivering rescue dogs helps Lily discover that home really…
8
Catering Christmas (2022)
★ 6.3/10Also tv movie and comedy
A fledgling caterer, Molly Frost, is hired by Jean Harrison, the perfectionistic director of the renowned Harrison Foundation, to cater this year’s annual Christmas Gala dinner. Things get complicated when Molly falls…
9
My Favorite Wedding (2017)
★ 6.9/10Also comedy and romance
Potential Northwestern fellow Tess Harper lasers through her best friend's wedding planning like the star doctor she hopes to soon become. In fact, Tess puzzles through any problem - provided it's not her own. When she…
10
A Royal Date for Christmas (2023)
★ 5.8/10Also romance and comedy
Bella Sparks, owner of Bella’s Boutique, takes on a demanding new client named Stefan, who needs to be outfitted for a week of high-stakes meetings and events after his luggage goes missing. Imagine Bella’s reaction…
11
Winter Castle (2019)
★ 6.8/10Also tv movie and romance
When Jenny attends her sister’s winter wedding at an ice hotel, her heart melts over the best man, the problem is he unexpectedly brings a “plus one,” seemingly dashing her hopes for a wintery romance.
12
Her Pen Pal (2021)
★ 6.8/10Also romance and comedy
Event planner Victoria can’t wait to attend –- and plan –- her best friend’s wedding in Paris. But when she finds out her ex is bringing a date, Victoria reconnects with her French childhood pen pal.
13
Brimming with Love (2018)
★ 6.3/10Also tv movie and romance
Allie is an aspiring journalist who meets Sam, a coffee shop owner who plays matchmaker for his customers. Allie agrees to be matched but going though Sam's process causes her to see that her perfect match might just…
14
A Kindhearted Christmas (2021)
★ 6.1/10Also tv movie and comedy
Jamie owns a sightseeing and tour company in the small town of Cooperville, New York. Navigating the holidays with enthusiasm is trickier for Jamie since her husband Matt passed. Matt loved Christmas and found…
15
The Enchanted Christmas Cake (2021)
★ 5.8/10Also tv movie and comedy
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.
16
The Seven Year Hitch (2012)
★ 6/10Also romance and comedy
Jennifer and Kevin are childhood best friends who have lived together, platonically, as adults for many years. When Jennifer decides to marry her cheating, manipulative boyfriend, Bryce Kevin has to stop the wedding to…
17
The Wrong Paris (2025)
★ 6.7/10Also romance and comedy
Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.
18
Holiday Harmony (2022)
★ 6.7/10Also romance and comedy
A likeable and talented underdog gets momentarily sidelined from chasing her musical dreams when her van breaks down in a welcoming small town just before Christmas.
19
Love in Winterland (2020)
★ 6.6/10Also tv movie and romance
Ally, a final contestant on a dating show, must face her high school sweetheart when she is chosen for the Hometown Date.
20
Secret Millionaire (2018)
★ 6.5/10Also romance and tv movie
When a bored millionaire (Steve Lund) is mistaken for a parking attendant by a beautiful girl (Siobhan Williams) who is protesting against his family’s intention of closing a local park, he uses the misunderstanding to…