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The Most Random Yet Brilliant Groups Of Celebrity Friends Holidaying Together

How do we wangle an invite?

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It's summer so, naturally, our Instagram accounts are flooded with enviable pictures of celebrities on incredible holidays.

We've become very accustomed to seeing the bikini selfies, yacht pictures and snaps of the picturesque Positano hillside. But every now and again, a post will catch our eye because of who the celebrity has chosen to go on holiday with.

Matthew McConaughey and Bono? Check. Paul McCartney and Karlie Kloss? It's happened. Scroll down for more.

Karlie Kloss, Harry Styles and Diane Von Furstenberg

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Any follower of DVF will be aware of her luxurious holidays with a bevy of famous friends (see further posts below) but this year's one was a real surprise.

The legendary designer has been sharing snaps from her yacht trip around the Sicilian coast and was joined by supermodel Karlie (also someone who appears to have many surprising jet-setting friends) and former One Directioner Harry Styles.

While Harry and Karlie have most probably crossed paths in similar circles (he did famously date Taylor Swift who she used to be joined at the hip of) we're not sure how this threesome came to be so close to holiday together. But we are here for it, nonetheless.

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Matthew McConaughey, Woody Harrelson, Sacha Baron Cohen, Isla Fisher, Bono and Chris Rock

In a photo reminiscent of Ellen DeGeneres' record-breaking Oscar selfie, Madonna and U2's longtime manager Guy O'Seary shared a photo from his July holiday in a beautiful Chateau in Provence in the south of France.

However, on second glances, this friendship group was no ordinary one: There was Sacha Baron Cohen (Borat/Ali G/Bruno etc), Isla Fisher, U2 frontman Bono, comedian Chris Rock, Matthew McConaughey and Camilla Alves and Woody Harrelson. Too much A-list for us to handle, to be honest.

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Karlie Kloss, Joshua Kushner, Ellie Goulding, Princess Beatrice and Misha Nonoo

A few months before their engagement announcement, supermodel Kloss and Kushner (brother to Jared Kushner, Ivanka Trump's husband and now a White House advisor to Donald Trump) holidayed in the Jordanian dessert with Ellie Goulding and her boyfriend Caspar Jopling, Princess Beatrice and the designer Misha Nonoo - who was rumoured to have set up Meghan Markle and Prince Harry. Who knew they were all such good friends?

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Paul McCartney, Misha Nonoo, Karlie Kloss and Josh Kushner

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Misha NoNoo//Instagram

Misha Nonoo and Karlie Kloss continue to surprise us with their group holidays.

Recently, the two - and their partners - joined legendary Beatle Paul McCartney and his wife Nancy aboard a yacht which sailed around the Italian coast. Dreamy.

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Bradley Cooper, Irina Shayk, Alison Williams, Anderson Cooper and Diane Von Furstenberg

Last summer, a group including designer Diane Von Fürstenberg, Girls actress Alison Williams and her husband Ricky Van Veen, Bradley Cooper and Irina Shayk, Watch What Happens Live presenter Andy Cohen and respected US news anchor Anderson Cooper all headed out to the French Polynesian island of Tahiti.

According to Vanity Fair, the unlikely group can be explained as follows: Anderson and Andy are very good friends, Andy is also very close with DVF, Andy is also good friends with Alison, Bradley has appeared on Andy's show and Irina has modelled for Diane. Got it?

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Justin Theroux, Sienna Miller, Emma Stone, Laura Harrier and Derek Blasberg

Chilling at the eternally exclusive resort of Hotel du Cap-Eden-Roc in Cannes a couple of months ago was Justin Theroux and Emma Stone, who both star in the upcoming Netflix series Maniac together, along with Sienna Miller, BlacKkKlansman actress Laura Harrier and journalist Derek Blasberg.

Now that is a seriously cool holiday gang we would very much like to be part of.

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Harry Styles, Kendall Jenner, Kris Jenner, Ellen DeGeneres and Portia de Rossi

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Over the Christmas and New Year holidays of 2015/2016, Kendall Jenner and Harry Styles seemed to answer everyone's questions of whether they were romantically involved when they were pictured kissing on a yacht in St Barts.

But this wasn't the end of it. On one of their first, and only, PDA moments that was caught on camera, Ellen DeGeneres and her wife Portia hopped on board the next day to hang out with the (sadly, short-lived) beautiful couple.

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Barack and Michelle Obama, Tom Hanks, Oprah Winfrey and Bruce Springsteen

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We're unsure if it's physically possible to get any more A-list than this holiday squad. After finishing his term as president of the United States, Barack and Michelle had Hanks, Springsteen and Winfrey join them on reportedly the world's 11th largest yacht around the French Polynesian islands in April 2017.

Hanks later told the Stephen Colbert show: 'Both Oprah and I were really pissed off because is this where we are in the world that Oprah and I cannot go on a billionaire's boat to Tahiti with a former president of the United States and not keep it secret, for god's sakes?' Oh, Tom <3

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Oprah Winfrey, Gayle King, Will.I.Am, Jimmy Iovine

While it's no surprise that longtime BFFs Oprah and TV host Gayle King holiday together, the fact they chose to spend their vacation clubbing in Ibiza might be one 0f the more unexpected aspects.

Not only this, on their 2015 trip to the White Isle, they also chose to hang out in the club with Will.I.Am and do tequila shots with Apple Music boss Jimmy Iovine.

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Olivia Blair
Entertainment Editor (Luxury)

Olivia Blair is Entertainment Editor (Luxury) at Hearst UK, working across ELLE, Esquire and Harper's Bazaar. Olivia covers all things entertainment and has interviewed the likes of Margot Robbie, Emma Stone, Michaela Coel and Ryan Gosling over the years.

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