Movies like The Holiday are always going to be capable of finding a massive audience, because if handled correctly, they can really elevate the genre.
Rom-com veteran Nancy Myers directs the holiday classic sees two down on their luck women swap homes and eventually fall for a couple of locals, with suitably schmaltzy results.
Because of this, we’ve got ten very similar movies that will pull at the heartstrings and have you laughing through tears at tales of love, loss, and sheer sentimentality. Let’s get started!
10 Cozy & Warm Romantic Movies Like The Holiday
1. Love Actually (2003)
One of the defining rom-coms of the 21st Century, Love Actually is another one of those movies like The Holiday that finds itself being re-watched by fans around the world on an annual basis.
Richard Curtis tells nine interconnected stories that follow love in all of its various forms, covering all aspects of society and the various dynamics that it takes to make a relationship work.
Star-studded, sweet, and sentimental, Love Actually is the textbook example of how to precision engineer a genre film to the target audience.
2. You’ve Got Mail (1998)
Sleepless in Seattle trio Nora Ephron, Tom Hanks and Meg Ryan reunite for another rom-com, and unsurprisingly the end result was a critical and commercial smash hit.
Two very different bookstore owners inadvertently start an online romance, with the incredibly on-the-nose message being that you shouldn’t judge a book by its cover.
Movies like The Holiday can be described as the big-screen equivalent of sitting by a roaring fire with a hot cup of cocoa, and  You’ve Got Mail definitely fits the bill.
3. Pretty Woman (1990)
If you enjoy movies like The Holiday but feel they lack a little bit of bite, Gary Marshall’s classic should satisfy your cravings, thanks to a couple of crackling leads and lashings of postmodernism.
A prostitute and a businessman fall in love with each other, and Pretty Woman throws ideas of class, status, wealth, and professionalism into something of a Cinderella story.
Julia Roberts’ performance rocketed her to the top of the Hollywood A-list, but there’s much more to Pretty Woman than just watching a star being born.
4. Bridget Jones’s Diary (2001)
Bridget Jones’s Diary turned Renee Zellweger into a star, and Sharon Maguire’s beloved rom-com would go on to earn over ten times its budget back at the box office.
The title heroine is a single writer that decides to take control of her own life, and soon finds herself in all sorts of mishaps and adventures.
One of the better movies like The Holiday that hits many of the same beats, Bridget Jones’s Diary has become required viewing for anyone with even a passing interest in the genre.
5. Hitch (2005)
A dating coach takes a new client under his wing, but finds himself developing feelings of his own as two potential relationships take shape in Andy Tennant’s fluffy rom-com.
Will Smith has charisma and star power for days, so it shouldn’t come as a surprise that he effortlessly breezes through his debut in the genre.
The supporting cast are all solid, and as predictable as things turn out in the end, the central premise is still fairly unique when it comes to romantic movies like The Holiday.
6. Last Holiday (2006)
Wayne Wang tackles the remake of a 1950 British comedy that follows a woman attempting to live the best life possible after receiving a terminal cancer diagnosis.
In the wrong hands, The Last Holiday could have turned out as either relentlessly depressing or offensively insensitive, but luckily the movie is nothing but entirely lovable from start to finish.
Movies like The Holiday always face a delicate balancing act to getting stuck in their own syrupy natures, and Queen Latifah’s energetic and positive performance stops that from happening.
7. The Proposal (2009)
Not all movies like The Holiday need to be aimed straight for the heart, and The Proposal focuses more on laughs than sentimentality, although there’s also plenty of that.
Sandra Bullock and Ryan Reynolds headline Anne Fletcher’s rom-com as a high-flying executive who ropes her subordinate into a sham engagement to stop herself from being deported.
Questionable morals aside, The Proposal coats through the motions based entirely on the charisma and chemistry of the two leads, which is in this case is more than enough.
8. Just Go with It (2011)
Adam Sandler isn’t the first name that comes to mind when you think of romantic leads, but he acquits himself well in Dennis Dugan’s relatively straightforward comedy.
Sandler plays a plastic surgeon who pretends to be married to avoid commitment and have a series of flings, but after roping in his assistant to play his wife, complications inevitably arise.
Jennifer Aniston can play these kinds of roles in her sleep, but she generated a surprising amount of sparks opposite Sandler, who thankfully dials down his usual shtick in favor of something more reserved.
9. The Ugly Truth (2009)
A TV producer finds herself pitted opposite a cocky alpha male on morning TV but wouldn’t you know it, the two polar opposites slowly start falling for each other.
Director Robert Luketic is no stranger to the rom-com, and he unsurprisingly proves to be a safe pair of hands behind the camera, although the script could have used a lot more work.
Gerard Butler’s gruff magnetism makes him a surprisingly good foil for the uptight Heigl, and their chemistry is the undoubted highlight of this more cynical spin on movies like The Holiday.
10. The Family Stone (2005)
An uptight woman struggles to deal with her boyfriend’s eccentric family when meeting them for the first time in Thomas Bezucha’s comedy that features plenty of drama as well as romance.
There’s an awful lot of jarring tonal shifts in The Family Stone but Sarah Jessica Parker, Craig T. Nelson, Rachel McAdams, Claire Danes and Diane Keaton are all fantastic in their roles.
Sometimes, movies like The Holiday can be elevated solely by the strength of their casts, and The Family Stone would be a far less enjoyable effort if it wasn’t for the ensemble.