Many of us have that lottery winner moment. The one where we think about how we’d spend our money if finances and having a regular day job were no longer an issue – if we had an endless bucket of money to spend wherever we wanted. Some dream of giant homes, expensive jewels, and fast cars. Others prefer to entertain the spirit of wanderlust. We think about all of the places we’d love to travel, the luxurious resorts that we’d stay at, the foods we’d try, and the places on a map of the world that we’d happily stroke off of our travel bucket list.
Being a part of the Kardashian clan comes with some serious benefits. Travelling in style with a big bank roll, along with various locals dying for all the press that comes with a family sighting, have many exclusive vacation destinations panting over a booking from them. Just like the rest of the family, Kylie Jenner knows what she wants in terms of her vacation. Usually favouring a warm locale where she can show off her bikini bod, the star has gone all out in terms of where and how she travels. Here’s a sneak peek at 15 exclusive vacation photos from the life of the rich, young, and fabulous Kylie Jenner.
15 Mad PDA In Mexico
What’s better than a trip to Mexico with your BAE? Back in 2017, Kylie Jenner’s Instagram was filled with pictures of her PDA filled vacation with her then on again/off again boyfriend Tyga, his son King and her BF Jordy Woods, along with her inner circle.
The young entrepreneur made sure to debut a number of bathing suits over the course of the trip, which arrived on the net via her own social media channels as well as through gossip sites like TMZ and The Daily Mail. While their relationship didn’t last to the end of the year, we’re certain the memories and photos of sun, and sand will be popping up online along with the luxury locale for quite some time.
14 Yachting In Paradise
Anyone who has ever tried to rent a charter boat has an idea of just how expensive it can be. Make that boat a chartered, luxury yacht with a crew of 11 and you can expect to pay more than many pay for their home. While in Greece the Kardashian crew chartered the O'Ceanos, complete with a bar and Jacuzzi.
The cost for this family fun time - around two hundred thousand US dollars.
But can you put a price tag on family time? Apparently you can. Brody and Kylie decided to use their time on deck to practice their diving skills from the top of the yacht into the ocean, while pregnant (at the time) Kim chilled on deck and enjoyed the view.
13 Turks And Cacaos Birthday Blast
Most of us celebrate our birthdays with some cake, a few drinks, some close friends, and family. If you’re Kylie Jenner, your 19th birthday is more extravagant than even the most sparkling champagne birthdays - it's a spectacular trip.
Kylie celebrated with her friends (many whom are models, to help make her photos extra attractive), family, and boyfriend Tyga for stunning photos and fun at an exclusive resort on the islands of Turks and Caicos. Kylie appears pleased as punch with her super celebration, and why wouldn't she be? She's literally celebrating her birthday in a paradise filled with sparkling sand and blue skies. Very different than blowing out the candles and making a wish!
12 A Day To Remember
Most of us would find an all-inclusive vacation for our 19th birthday to be an extravagant undertaking. When Kylie celebrated her birthday, she wasn't going to spare any expense.
This weekend getaway reportedly cost $10,000 a night to rent.
This is a photo of the 50 million dollar property where she and her inner circle roamed, posed in bikinis for endless social media pics, and let the wind blow through their hair. Are you green with envy yet? Although it's absolutely stunning, we can't imagine many teens willing or able to spend a good chunk of a year’s salary for a weekend away. Then again, most 19 year olds aren't Kylie, and even though we weren't invited, at least we get to see the photos!
11 Memories Of Mexico
Some people go overboard on their Christmas spending, and Kylie Jenner is no different. In 2016, after selling her first house for a cool four million dollars, and flipping a Hidden Hills house for over five million dollars, Kylie decided that it was time to treat herself to a pricey New Year's getaway. The young mogul rented an expansive beachfront home located in Punta Mita, Mexico.
The villa, called Casa Amamara (given its name as a tribute the Huichol people and their goddess of life), is a $16,000 a night.
It contains 12 bedrooms and 13 bathrooms. For their multi-thousand dollar rental the couple were able to enjoy a paradise filled with a gigantic pool, well-groomed greenery, and breathtaking views.
10 Saying Hello To Hawaii
Ever wonder how Kylie Jenner keeps up with the sun kissed skin of her siblings? We're guessing it has to do with the time the family spends in the sun. This photo is a throwback to a 2012 family trip to Hawaii where the reality TV family soaked up some sun and seclusion.
We often forget just how young Kylie and Kendall are, (Kylie was just 14 and Kendall 16 at the time of this photo), simply because they've been on our radar and televisions for so many years. In this picture the two teens simply seem to be enjoying a little quiet sister time on a secluded beach without the hustle and bustle of their, or their family's celebrity.
9 Boating & Boasting In Greece
A family trip to Greece is a once in a life time for most, unless you're filming it as a part of your E! Reality Show, Keeping Up with the Kardashians. Fans were able to get a sneak peek of the trip before the season began thanks to the endless social media posts from the sisters highlighting their designer sandals, Mediterranean landscapes, and bikini clad bodies.
When Kendall posted pictures of herself and sis Kylie in their swim suits, Kylie rocking a cool mint green bikini wrote, "This is bliss man! dee dee deee".
So are you jealous yet? The family topped off their trip with some serious boating and posing time on a luxury yacht, horseback riding, ATVing, and delicious dining with a fabulous view.
8 Beverly Hills Rental
We're guessing that this exclusive Beverly Hills rental is the equivalent of a staycation for the young and rich Kylie Jenner.
While she was renovating her Hidden Hills home she decided to rent an enormous cliff-top Beverly Hills Mansion for a whopping 125K per month.
The rental digs, on a four acres property, houses the 6,025 square foot pad, and includes five bedrooms, and seven bathrooms.There is a pool, tennis court, movie theatre, mini golf course, and a private vineyard. Did we mention the fantastic view of the city? Anyone who was interested in purchasing Kylie's rental was welcome to, since the place was for sale at the time she was renting, so long as they have 35 million dollars in their bank account.
7 Trip To Thailand
Many travelers will boast that even though Thailand is a popular tourist destination, the hordes of people visiting each year have not ruined the sense of beauty and paradise offered. With crisp white sand and bright aqua waters, it's no wonder that Kendall and Kylie Jenner couldn't wait to get to the beach on their 2014 trip.
The two were anxious to show off their bathing suit bodies for paparazzi and their own private social media accounts alike, lounging by the water in their best swimwear. Kylie soaked up the sand and some sun in this sleek black bikini.
6 Heading To Houston
Sometimes, but very rarely, Kylie Jenner's travel plans don't involve a beach. Not too long ago Kylie Jenner and Travis Scott decided to take a trip to Houston (Scott's hometown). The two were routinely recognized by fans as they enjoyed one of the lowest key vacations possible if you're a Kardashian. The pair relaxed with a takeout lunch at MOD Pizza. An eye witness said,
“Kylie and Travis came in right after the lunch rush. There were only about eight people total in the restaurant. They came in at the perfect time because no one was in here."
The pair managed to fly under the radar and didn't attract a lot of attention for their takeout meal, but were back in the public eye when they enjoyed a Houston Rocket's game sitting court-side.
5 Long Weekend Lounging
Pool parties are the perfect place to pose, just ask Kylie and Hailey Baldwin who spent their Memorial Day posing with their micro tattoos and posting the pics on social media. Who needs to take a weekend away when your house is a virtual paradise anyway, and you can celebrate in the comfort of your own home?
The lovely ladies posted both close up and personal shots of their vibrant coloured bikinis and poolside antics. Sometimes a long weekend at home is the perfect way to reconnect with friends and family. Jenner and Baldwin enjoyed the company of Kylie's sister Kendall Jenner and model friend Cami Morrone, all clad in bikinis, enjoying the sun and relaxation, and dipping their feet into the Jacuzzi.
4 Philanthropy In Peru
Sometimes it's time to put your money where your mouth is, and that's just what Kylie Jenner did when she decided to put her money and time towards a good cause. In her series, Life of Kylie, Jenner was filmed in Peru along with some friends and her mother, Kris.
Kylie had partnered with a charity called Smile Train for a special-edition lip kit recently. Funds raised help provide surgery to correct cleft lip and palate for children in need. Kylie visited a health clinic in Lima as a part of this collaboration and met with several children who had undergone surgery. During the visit, Kylie was photographed cuddling a baby, and later visited some baby goats and alpacas in Cusco. Kylie posted on social media that her visit was the "Best Day Ever."
3 Modern Miami Mansion
Miami is a vacation destination of the young and eligible. This is no different for young makeup mogul Kylie Jenner. While Kylie and her crew holidayed in Miami they enjoyed their time in an 18 million dollar waterfront mansion.
The home is located on Hibiscus Island and has a breath-taking view of South Beach just outside the door. The place has six bedrooms, seven bathrooms, an infinity edge lap pool, and a movie theatre with leather recliners. Want to rent it with your BFFs? It's listed on Airbnb for ten thousand dollars a night for anyone who wants to feel fancy and fabulous for a weekend and has the cash to burn. Kylie's favourite feature of the home was the elevator, which she repeatedly featured on Snapchat.
2 Stylish Ski Trip
Turns out Kylie Jenner fancies herself more of a snowboarder than a ski bunny, who knew?
"The name speaks to the size of the mountains, the expanse of the valleys, the incredible number of crystal clear mountain lakes and the endless opportunities for adventure just outside your door."
Sounds breathtaking and envy inducing. Kylie proves that she can look just as on fleek bundled up as she can in her bikini, and is a celebrity for all seasons. The star went on a cool and collected vacation with boyfriend Tyga and some of her inner circle to hit the slopes in style. Kylie even posted video on Instagram of her snowboarding skills while shredding at Mammoth Lakes, California, a highly fashionable ski vacation destination.
1 New York City Nights
Is New York City an impressive enough destination to mend a broken heart? Apparently Kylie Jenner is putting this theory to the test, with the pregnant celeb spending time in one of her favourite places to help distract her from her recent split with Travis Scott.
A source who is close to Kylie reportedly said, "Kylie really thought her future was with Travis and the baby, so the split came as a huge surprise."
"She’s going through a very dark time with her mood swings and changing body shape, plus her romance is in ruins, so she’s decided she needs a change and has always loved New York." It's believed that she's considering a move to the Big Apple, hoping that it will help give her and baby a fresh start.