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20 Movies Like The Holiday (2006)

He's Just Not That Into You (2009) poster

1 He's Just Not That Into You (2009) ★ 6.4

Similar to The Holiday (2006)?

The needy Gigi Haim is a young woman seeking her prince charming somewhere amongst her unsuccessful dates. After dating estate agent Conor Barry, Gigi anxiously expects to receive a phone call from him. However Conor never calls her. Gigi decides to go to the bar where he frequents to see him, but she meets his friend Alex who works there. They become friends and Alex helps Gigi to interpret the subtle signs given out by her dates.
Ghosts of Girlfriends Past (2009) poster

2 Ghosts of Girlfriends Past (2009) ★ 5.8

Similar to The Holiday (2006)?

Connor Mead is a womanizer who can dump three girlfriends. At the same time. By conference call. So when he gets to his brother's wedding, his only goal is to seduce the bridesmaid who hasn't yet fallen into his net. But the ghost of his late Uncle Wayne - the same one who taught him to fall in love with women and leave them - has another thing on his mind.

He wants to restore Connor's faith in true love, and that's a real challenge, one that will require the help of the Ghosts of Ex-Girlfriends.

The Ugly Truth (2009) poster

3 The Ugly Truth (2009) ★ 6.4

Similar to The Holiday (2006)?

An uptight television producer takes control of a morning show segment on modern relationships hosted by a misogynistic man.
Rumor Has It... (2005) poster

4 Rumor Has It... (2005) ★ 5.5

Like The Holiday (2006) film?

Sarah Huttinger is a woman who learns that her family was the inspiration for the book and film "The Graduate" -- and that she just might be the offspring of the well-documented event.
Leap Year (2010) poster

5 Leap Year (2010) ★ 6.4

Like The Holiday (2006) film?

Anna Brady plans to travel to Dublin, Ireland to propose to her boyfriend Jeremy on February 29, leap day, because, according to Irish tradition, a man who receives a marriage proposal on a leap day must accept it.
Must Love Dogs (2005) poster

6 Must Love Dogs (2005) ★ 5.9

Like The Holiday (2006) film?

A thirty-something preschool teacher looks to the personals for a change of pace and a relationship, with hilarious results.
The Break-Up (2006) poster

7 The Break-Up (2006) ★ 5.8

Like The Holiday (2006) film?

In a bid to keep their luxurious condo from their significant other, a couple's break-up proceeds to get uglier and nastier by the moment.
Serendipity (2001) poster

8 Serendipity (2001) ★ 6.8

A couple search for each other years after the night they first met, fell in love, and separated, convinced that one day they'd end up together.
How to Lose a Guy in 10 Days (2003) poster

9 How to Lose a Guy in 10 Days (2003) ★ 6.4

Journalist Andy Anderson decides to write an article on "Typical Mistakes Women Make to Drive Men Away". She plans to find a guy, get an acquaintance, and then get him to break up with her by his behavior. The editor gives her ten days to do this. To Andy's misfortune, her choice falls on a young advertising agent, Benjamin Barry, who has just made a bet with his boss that he can make a girl fall in love with him in ten days. Can such a strange acquaintance, based on a gamble and mixed up in lies, lead to reciprocity?
Last Holiday (2006) poster

10 Last Holiday (2006) ★ 6.5

Upon learning of a terminal illness, a shy woman decides to sell all her possessions and live it up at a posh Central European hotel.
The Family Stone (2005) poster

11 The Family Stone (2005) ★ 6.3

An uptight, conservative businesswoman accompanies her boyfriend to his eccentric and outgoing family's annual Christmas celebration and finds that she's a fish out of water in their free-spirited way of life.
Failure to Launch (2006) poster

12 Failure to Launch (2006) ★ 5.6

Despite being in his 30s, the handsome Tripp has been hesitant to leave his father's house and get his own family nest. Every time he finds a good reason, in his opinion, for this.

But one day Tripp's parents took it upon themselves to arrange his fate. They hired a beautiful and talented girl, hoping that their son, falling in love with her, will finally leave their home...

A Good Year (2006) poster

13 A Good Year (2006) ★ 6.9

A British investment broker inherits his uncle's chateau and vineyard in Provence, where he spent much of his childhood. He discovers a new laid-back lifestyle as he tries to renovate the estate to be sold.
Hitch (2005) poster

14 Hitch (2005) ★ 6.6

Alex "Hitch" Hitchens is a legendary New York City "matchmaker doctor. He has helped a lot of men get the women of their dreams to like him. Hitch is not disinterested; he receives a fee for his work, but he is careful to keep his way of making a living a secret.

Hitch's new client is Albert, a shy accountant who is madly in love with glamorous starlet Allegra Cole. For Hitch, this case should be the pinnacle of his career. However, while working on the case, he suddenly meets a worthy adversary in the form of the spectacular and shrewd Sarah Melas, a gossip columnist who follows Allegra's every move.

Something's Gotta Give (2003) poster

15 Something's Gotta Give (2003) ★ 6.7

Is Something's Gotta Give (2003) similar to The Holiday (2006) film?

A swinger on the cusp of being a senior citizen with a taste for young women falls in love with an accomplished woman closer to his age.
Just Go with It (2011) poster

16 Just Go with It (2011) ★ 6.4

Is Just Go with It (2011) similar to The Holiday (2006) film?

Danny meets Palmer, and to impress her, he talks about his nonexistent wife and the hardships of married life. Instead of the expected sympathy, Palmer wants to meet his wife, and Danny urgently needs to figure out how to get out of such an interesting situation. Fortunately, he has a colleague he knows, Katherine, who is charming and has children, and who will play the role of his family for a while.

What Happens in Vegas (2008) poster

17 What Happens in Vegas (2008) ★ 6.1

Is What Happens in Vegas (2008) similar to The Holiday (2006) film?

After a night of partying in Sin City, two complete strangers wake up in the same bed and try to reconstruct the events of the evening. It turns out that they got married and hit a huge jackpot. And now with a clear head the newlyweds (each by himself) develop a plan to get rid of his "other half" and get all the jackpot. Where money is involved, there is no place for love. Although all sorts of things happen in Vegas...
It's Complicated (2009) poster

18 It's Complicated (2009) ★ 6.5

Is It's Complicated (2009) similar to The Holiday (2006) film?

When attending their son's college graduation, a couple reignite the spark in their relationship. But the complicated fact is they're divorced and he's remarried.
In Her Shoes (2005) poster

19 In Her Shoes (2005) ★ 6.5

Is In Her Shoes (2005) similar to The Holiday (2006) film?

Strait-laced Rose breaks off relations with her party girl sister, Maggie, over an indiscretion involving Rose's boyfriend. The chilly atmosphere is broken with the arrival of Ella, the grandmother neither sister knew existed.
The Proposal (2009) poster

20 The Proposal (2009) ★ 6.7

Is The Proposal (2009) similar to The Holiday (2006) film?

The main character of the film is a responsible manager who faces deportation to Canada. In order to avoid exile in the land of lakes, the heroine is ready to do anything - even fictitiously marry her young assistant...

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