Movies Like Captiva Island

If you liked Captiva Island (1995), a comedy movie directed by John Biffar, 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
Duplex (2003)
★ 6.1/10Also comedy
When a young couple buys their dream home, they have no idea what the sweet little old lady upstairs is going to put them through!
2
Thunderstruck (2012)
★ 6.2/10Also comedy
After NBA star Kevin Durant switches talent with 16 year old Brian, the teenager becomes the star of his high school team, but Durant starts struggling and eventually learns an important lesson.
3
Gabriel Iglesias: I'm Sorry for What I Said When I Was Hungry (2016)
★ 7.1/10Also comedy
Hawaiian-shirt enthusiast Gabriel "Fluffy" Iglesias finds the laughs in racist gift baskets, Prius-driving cops and all-female taco trucks.
4
The Three Stooges (2012)
★ 5.8/10Also comedy
Left on the doorstep of an orphanage run by nuns, three newborn knuckleheads grow up to be finger-poking, nyuk-nyuking janitors named Larry, Curly and Moe. When they learn that financial problems will soon force the…
5
Taking Care of Business (1990)
★ 6.3/10Also comedy
An uptight advertising exec has his entire life in a filofax organizer which mistakenly ends up in the hands of a friendly convict who poses as him.
6
American Dreamer (2022)
★ 6/10Also comedy
In this winsome comedy, an entitled Economics professor pursues a tactic to buy an ailing widow’s mansion for nothing, but he quickly realizes that his seemingly foolproof strategy won’t be as easy as he thought.
7
Fired Up! (2009)
★ 6.1/10Also comedy
Popular high schoolers and best friends Shawn and Nick decide to ditch football camp for cheerleader camp. For the girls and for the glory.
8
Stewie Griffin: The Untold Story (2005)
★ 6.9/10Also comedy
The maniacal baby of the Griffin family, Stewie, meets his future self. In doing this he discovers that his future image is not what he has anticipated because of a near death experience.
9
Problem Child 2 (1991)
★ 6/10Also comedy
Junior and his father, Ben, move from Cold River to Mortville. Junior becomes threatened by Ben's desire to date again and find a new mother for Junior, and sabotages each of his dates.
10
The Thursday Murder Club (2025)
★ 6.6/10Also comedy
A group of senior sleuths passionate about solving cold cases get plunged into a real-life murder mystery in this comic crime caper.
11
Rock 'n' Roll High School (1979)
★ 6.3/10Also comedy
A group of rock-music-loving students, with the help of the Ramones, take over their school to combat its newly installed oppressive administration.
12
The Distinguished Gentleman (1992)
★ 6/10Also comedy
A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, the U.S. Congress, where the money flows…
13
Swindle (2014)
★ 7/10Also comedy
A boy named Griffin finds a valuable multi-million dollar baseball card. After accidentally selling the card for a million dollar loss, he enlists the help of his best friend Ben and his colleagues to regain the…
14
The Mouse That Roared (1959)
★ 6.4/10Also comedy
The Duchy of Grand Fenwick decides that the only way to get out of their economic woes is to declare war on the United States, lose and accept foreign aid. They send an invasion force (in chain mail, armed with bows…
15
Jim Jefferies: Freedumb (2016)
★ 7.2/10Also comedy
Returning for a second Netflix comedy special, Jim Jefferies unleashes his famously ferocious black humor to a packed house in Nashville, Tennessee.
16
Daria in 'Is It Fall Yet?' (2000)
★ 7.3/10Also comedy
Daria is a 17-year-old girl who is a little too smart and funny to fit in with the crowd. It’s summertime and the livin' is hard. Daria finds herself forced into volunteering at the OK To Cry Corral, a summer camp for…
17
Shorts (2009)
★ 5.9/10Also comedy
A young boy's discovery of a colorful, wish-granting rock causes chaos in the suburban town of Black Falls when jealous kids and scheming adults alike set out to get their hands on it.
18
Psych: The Movie (2017)
★ 7.2/10Also comedy
The ambitious friends come together during the holidays after a mystery assailant targets one of their own. A comedic thrill-ride follows, as the wild and unpredictable Psych team pursues the bad guys, justice … and…
19
Grown Ups 2 (2013)
★ 6.2/10Also comedy
Lenny has relocated his family back to the small town where he and his friends grew up. This time around, the grown ups are the ones learning lessons from their kids on a day notoriously full of surprises—the last day…
20
The Ladykillers (2004)
★ 6.1/10Also comedy
An eccentric, if not charming Southern professor and his crew pose as a band in order to rob a casino, all under the nose of his unsuspecting landlord – a sharp old woman.