Movies Like Summer Vacation 1999

If you liked Summer Vacation 1999 (1988), a drama and romance movie directed by Shusuke Kaneko, 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
Heartstopper Forever (2026)
★ 7.2/10Also romance and drama
It's a new school year for the Truham-Higgs gang. As Nick and Charlie's relationship deepens, their thoughts turn to life after the last bell rings.
2
Winter's Tale (2014)
★ 6.3/10Also drama and fantasy
A burglar falls for an heiress as she dies in his arms. When he learns that he has the gift of reincarnation, he sets out to save her.
3
Aristotle and Dante Discover the Secrets of the Universe (2023)
★ 7.5/10Also romance and drama
Two teenage Mexican-American loners in 1987 El Paso explore a new, unusual friendship and the difficult road to self-discovery.
4
Yes, No, or Maybe? (2020)
★ 6.8/10Also drama and romance
A polished newscaster hides behind a mask when he meets a gentle artist—but the lie complicates everything when feelings start to grow.
5
Marked Men: Rule + Shaw (2025)
★ 6.7/10Also romance and drama
Shaw Landon has loved Rule Archer from the moment she laid eyes on him. Rule, a fiery-tempered rebel tattoo artist, doesn’t have time for a good girl pre-med student like Shaw — even if she’s the only one who can see…
6
Peter Ibbetson (1935)
★ 7/10Also drama and fantasy
When his mother dies, young Peter Ibbetson leaves Paris and his best friend, Mary, behind to live with a severe uncle in England. Years later, Peter is an architect with little time for women, until he begins a project…
7
Endless Love (2014)
★ 6.9/10Also drama and romance
A privileged girl and a charismatic boy's instant desire sparks a love affair made only more reckless by parents trying to keep them apart.
8
My Policeman (2022)
★ 7.5/10Also drama and romance
In the late 1990s, the arrival of elderly invalid Patrick into Marion and Tom’s home triggers the exploration of seismic events from 40 years previous: the passionate relationship between Tom and Patrick at a time when…
9
Departure (2016)
★ 6.3/10Also drama and romance
An English mother and her teenage son spend a week preparing the sale of their remote holiday house in the South of France. Fifteen-year-old Elliot struggles with his dawning sexuality and an increasing alienation from…
10
Given (2020)
★ 8.2/10Also drama and romance
Haruki secretly had feelings for Akihiko for years, but Akihiko was still in a relationship with his roommate, the violinist Ugetsu Murata. Haruki, Akihiko, and Ugetsu's love clashes and starts to move forward.
11
Hello, Goodbye, and Everything in Between (2022)
★ 6.1/10Also romance and drama
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?
12
Tuff Turf (1985)
★ 5.9/10Also drama and romance
The new guy in a Los Angeles high school, Morgan, does some singing and fights hotshot Nick over disco dancer Frankie.
13
After (2019)
★ 7.1/10Also drama and romance
Tessa Young is a dedicated student, dutiful daughter and loyal girlfriend to her high school sweetheart. Entering her first semester of college, Tessa's guarded world opens up when she meets Hardin Scott, a mysterious…
14
The Object of My Affection (1998)
★ 5.8/10Also drama and romance
A pregnant New York social worker begins to develop romantic feelings for her gay best friend, and decides she'd rather raise her child with him, much to the dismay of her overbearing boyfriend.
15
Wicked (2021)
★ 7.8/10Also fantasy and romance
Ivy Morgan, a college student in New Orleans, falls for Ren Owens, the last person she expected to enter her rigidly controlled life.
16
The Secret: Dare to Dream (2020)
★ 7.4/10Also drama and romance
A widow with three children hires a handyman to fix her house during a major storm. When not doing home repairs, he shares his philosophy of believing in the power of the universe to deliver what we want.
17
The Vanishing of Sidney Hall (2018)
★ 6.7/10Also drama and mystery
Over the course of 12 years, and three stages of life, Sidney Hall falls in love, writes the book of a generation and then disappears without a trace.
18
Blue Story (2019)
★ 7.3/10Also drama and romance
Blue Story is a tragic tale of a friendship between Timmy and Marco, two young boys from opposing postcodes. Timmy, a shy, smart, naive and timid young boy from Deptford, goes to school in Peckham where he strikes up a…
19
Sahara (1983)
★ 5.9/10Also drama and romance
Intent on winning a competition in place of her distinguished late father, beautiful young heiress Dale takes on the guise of a man and competes in his spot, embarking on a car race that crosses the unforgiving Sahara…
20
Before I Fall (2017)
★ 7/10Also drama and fantasy
Samantha Kingston has everything. Then, everything changes. After one fateful night, she wakes up with no future at all. Trapped into reliving the same day over and over, she begins to question just how perfect her…