Best movies like Last Holiday

Similar in 82%

Elizabethtown (2005)

Plot Summary:

Drew Baylor is fired after causing his shoe company to lose hundreds of millions of dollars. To make matters worse, he's also dumped by his girlfriend. On the verge of ending it all, Drew gets a new lease on life when he returns to his family's small Kentucky hometown after his father dies. Along the way, he meets a flight attendant with whom he falls in love.

Similar in 82%

Griffin & Phoenix (2006)

Plot Summary:

A terminally ill man falls in love with a woman who has a secret that threatens their time spent together.

Similar in 86%

New Year's Eve (2011)

Plot Summary:

The lives of several couples and singles in New York intertwine over the course of New Year's Eve.

Similar in 82%

New in Town (2009)

Plot Summary:

Lucy Hill is an ambitious up-and-coming executive living in Miami. She loves her shoes, she loves her cars and she loves climbing the corporate ladder. When she is offered a temporary assignment – in the middle of nowhere – to restructure a manufacturing plant, she jumps at the opportunity, knowing that a big promotion is close at hand. What begins as a straight-forward assignment becomes a life-changing experience as Lucy discovers greater meaning in her life and, most unexpectedly, the man of her dreams.

Similar in 89%

Because I Said So (2007)

Plot Summary:

In an effort to prevent family history from repeating itself, meddlesome mom Daphne Wilder attempts to set up her youngest daughter, Milly, with Mr. Right. Meanwhile, her other daughters try to keep their mom's good intentions under control.

Similar in 86%

When in Rome (2010)

Plot Summary:

After fishing out coins from a water fountain in Italy, cynical New Yorker Beth Harper finds herself being wooed by several ardent suitors. As she deals with the attention, Beth tries to figure out whether a charming reporter really loves her.

Similar in 76%

Sweet Home Alabama (2002)

Plot Summary:

New York fashion designer Melanie Carmichael suddenly finds herself engaged to the city's most eligible bachelor. But Melanie's past holds many secrets, including Jake, the redneck husband she married in high school, who refuses to divorce her. Bound and determined to end their contentious relationship once and for all, Melanie sneaks back home to Alabama to confront her past.

Similar in 88%

It Could Happen to You (1994)

Plot Summary:

Charlie Lang is a simple, kindhearted New York City cop. When he realizes he has no money to tip waitress Yvonne Biasi, Lang offers her half the winnings of his lottery ticket. Amazingly, the ticket happens to be a winner, in the sum of $4 million. True to his word, Lang proceeds to share the prize money with Biasi, which infuriates his greedy wife, Muriel. Not content with the arrangement, Muriel begins scheming to take all the money.

Similar in 78%

Sweet November (2001)

Plot Summary:

Nelson is a man devoted to his advertising career in San Francisco. One day, while taking a driving test at the DMV, he meets Sara. She is very different from the other women in his life. Nelson causes her to miss out on taking the test and later that day she tracks him down. One thing leads to another and Nelson ends up living with her through a November that will change his life forever.

Similar in 78%

P.S. I Love You (2007)

Plot Summary:

A young widow discovers that her late husband has left her 10 messages intended to help ease her pain and start a new life.

Similar in 77%

Sex and the City 2 (2010)

Plot Summary:

Carrie, Charlotte, and Miranda are all married now, but they're still up for a little fun in the sun. When Samantha gets the chance to visit one of the most extravagant vacation destinations on the planet and offers to bring them all along, they surmise that a women-only retreat may be the perfect excuse to eschew their responsibilities and remember what life was like before they decided to settle down.

Similar in 83%

Raising Helen (2004)

Plot Summary:

Helen Harris has a glamorous, big-city life working for one of New York's hottest modeling agencies. But suddenly her free-spirited life gets turned upside down when she must chose between the life she's always loved, and the new loves of her life!.

Similar in 89%

Life as We Know It (2010)

Plot Summary:

After a distastrous first date for caterer Holly and network sports director Messer, all they have is common is a dislike for each other and their love for their goddaughter Sophie. But when they suddenly become all Sophie has in this world, Holly and Messer must set their differences aside. Juggling careers and social calendars, they'll have to find common ground while living under the same roof.

Similar in 84%

Uptown Girls (2003)

Plot Summary:

Molly Gunn, the freewheeling daughter of a deceased rock legend, is forced to get a job when her manager steals her money. As nanny for precocious Ray, the oft ignored daughter of a music executive she learns what it means to be an adult while teaching Ray how to be a child.

Similar in 85%

No Reservations (2007)

Plot Summary:

Master chef Kate Armstrong runs her life and her kitchen with intimidating intensity. However, a recipe for disaster may be in the works when she becomes the guardian of her young niece while crossing forks with the brash sous-chef who just joined her staff. Though romance blooms in the face of rivalry, Kate needs to look outside the kitchen to find true happiness.

Similar in 85%

Under the Tuscan Sun (2003)

Plot Summary:

After a rough divoce, Frances, a 35 year old book editor from San Francisco takes a tour of Tuscany at the urgings of her friends. On a whim she buys Bramasole, a run down villa in the Tuscan countryside and begins to piece her life together starting with the villa and finds that life sometimes has unexpected ways of giving her everything she wanted.

Similar in 79%

While You Were Sleeping (1995)

Plot Summary:

A love story built on a misunderstanding. A transit worker pulls commuter Peter off the tracks after he's mugged. But while he's in a coma, his family mistakenly thinks she's Peter's fiancée, and she doesn't correct them. Things get more complicated when she falls for his brother, who's not quite sure that she's who she claims to be.

Similar in 84%

The Family Stone (2005)

Plot Summary:

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.

Similar in 76%

Return to Me (2000)

Plot Summary:

It took a lot of cajoling to get Bob (Duchovny), a recently widowed architect, to go on a blind date at a quirky Irish-Italian eatery. Once there, he's smitten instantly not with his date but with the sharp-witted waitress, Grace (Driver). Everything seems to be going great until an unbelievable truth is revealed, one that could easily break both of their hearts for good.

Similar in 77%

Leap Year (2010)

Plot Summary:

When yet another anniversary passes without a marriage proposal from her boyfriend, Anna decides to take action. Aware of a Celtic tradition that allows women to pop the question on Feb. 29, she plans to follow her lover to Dublin and ask him to marry her. Fate has other plans, however, and Anna winds up on the other side of the Emerald Isle with handsome, but surly, Declan -- an Irishman who may just lead Anna down the road to true love.

Similar in 89%

Maid in Manhattan (2002)

Plot Summary:

Marisa Ventura is a struggling single mom who works at a posh Manhattan hotel and dreams of a better life for her and her young son. One fateful day, hotel guest and senatorial candidate Christopher Marshall meets Marisa and mistakes her for a wealthy socialite. After an enchanting evening together, the two fall madly in love. But when Marisa's true identity is revealed, issues of class and social status threaten to separate them. Can two people from very different worlds overcome their differences and live happily ever after?.

Similar in 84%

Pretty Woman (1990)

Plot Summary:

When a millionaire wheeler-dealer enters a business contract with a Hollywood sex worker Vivian Ward, he loses his heart in the bargain.

Similar in 82%

27 Dresses (2008)

Plot Summary:

Altruistic Jane finds herself facing her worst nightmare as her younger sister announces her engagement to the man Jane secretly adores.

Similar in 84%

50 First Dates (2004)

Plot Summary:

Henry is a player skilled at seducing women. But when this veterinarian meets Lucy, a girl with a quirky problem when it comes to total recall, he realizes it's possible to fall in love all over again…and again, and again. That's because the delightful Lucy has no short-term memory, so Henry must woo her day after day until he finally sweeps her off her feet.

Similar in 88%

Two Weeks Notice (2002)

Plot Summary:

Dedicated environmental lawyer Lucy Kelson goes to work for billionaire George Wade as part of a deal to preserve a community center. Indecisive and weak-willed George grows dependent on Lucy's guidance on everything from legal matters to clothing. Exasperated, Lucy gives notice and picks Harvard graduate June Carter as her replacement. As Lucy's time at the firm nears an end, she grows jealous of June and has second thoughts about leaving George.

Similar in 88%

Letters to Juliet (2010)

Plot Summary:

An American girl on vacation in Italy finds an unanswered "letter to Juliet" -- one of thousands of missives left at the fictional lover's Verona courtyard, which are typically answered by a the "secretaries of Juliet" -- and she goes on a quest to find the lovers referenced in the letter.

Similar in 83%

The Holiday (2006)

Plot Summary:

Two women, one (Cameron Diaz) from America and one (Kate Winslet) from Britain, swap homes at Christmastime after bad breakups with their boyfriends. Each woman finds romance with a local man (Jude Law, Jack Black) but realizes that the imminent return home may end the relationship.

Similar in 86%

How to Lose a Guy in 10 Days (2003)

Plot Summary:

An advice columnist, Andie Anderson (Kate Hudson), tries pushing the boundaries of what she can write about in her new piece about how to get a man to leave you in 10 days. Her editor, Lana (Bebe Neuwirth), loves it, and Andie goes off to find a man she can use for the experiment. Enter executive Ben Berry (Matthew McConaughey), who is so confident in his romantic prowess that he thinks he can make any woman fall in love with him in 10 days. When Andie and Ben meet, their plans backfire.

Similar in 82%

The Bucket List (2007)

Plot Summary:

Corporate billionaire Edward Cole and working class mechanic Carter Chambers are worlds apart. At a crossroads in their lives, they share a hospital room and discover they have two things in common: a desire to spend the time they have left doing everything they ever wanted to do and an unrealized need to come to terms with who they are. Together they embark on the road trip of a lifetime, becoming friends along the way and learning to live life to the fullest, with insight and humor.

Similar in 84%

Hitch (2005)

Plot Summary:

Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.