14 High-End Vacation Destinations of the Rich and Famous

A-listers spend a lot of time working, but they also know how to kick back and relax in style. Many members of the wealthy jet-set crowd own vacation properties in the world’s most beautiful locales, while others rent out luxury accommodations featuring all the top amenities.

From the slopes of Telluride to the beaches of Bali, the below destinations are top picks among celebrity travelers the world over.

Larry Ellison owns many homes he could use as vacation retreats. The Oracle founder, who is now worth more than $153 billion, according to Forbes, can often be found on the Hawaiian island he purchased in 2012, though.

Ellison paid $300 million to buy 98% of Lanai, which boasts two Four Seasons resorts, as well as world-class golf courses. The lowest rate found for a room at the Four Seasons Resort Lanai was $1,075 per night.

Bill and Melinda Gates were married on Lanai in 1994, and since Ellison overhauled the Four Seasons Resort Lanai in 2016, it’s been inundated with celebrity guests. Some of the high-profile vacationers include Cindy Crawford, Will Smith and Derek Jeter.

Running Facebook is a big job, so it’s no surprise that Mark Zuckerberg — the company’s co-founder, chairman and CEO — likes to jet off to Hawaii to relax. In 2014, he purchased the 357-acre Kahu’aina Plantation on Kauai’s North Shore for $66 million, according to Forbes. Zuckerberg — whose net worth exceeds $174.5 billion — then bought 350 more acres of land at the adjacent Pila’a Beach for $49.6 million.

Carlos Santana, the famous musician, sold his vacation home on the island for about $12 million a few years ago.

Tropical locales aren’t the only places the rich and famous go to relax. Hewlett Packard Enterprise CEO Meg Whitman heads to the mountains for leisure time.

Along with her husband, Whitman, whose net worth Forbes puts at $3.4 billion, owns a ski resort condo, dude ranch and hundreds of acres of land around the Alta Lakes in Telluride. It has been reported that her Skyline Ranch is worth around $18 million.

Tony Robbins spends most of his time working — in fact, he is generally on the road 200 days per year. The New York Times No. 1 best-selling author enjoys spending downtime at his tropical hideaway, Namale Resort, though.

Robbins, who has a net worth of $600 million, according to Celebrity Net Worth, created the 525-acre resort in the Fiji islands. Popular with A-listers, the site has hosted numerous stars, including Edward Norton and Meg Ryan. Rates for rooms at Namale Resort start at $1,755 per night, but discounts are available for booking multi-night stays.

The Hamptons are associated with the rich and famous as a high-end vacation destination. Jerry Seinfeld has owned a 12-acre East Hampton estate since 2000, purchased from Billy Joel for $32 million. In 2017, Jay-Z and Beyoncé bought a 12,000-square-foot East Hampton home for nearly $26 million. Billy Joel recently wanted to return and purchased a 3,500-square-foot home for $10.7 million.

If you want to travel like a millionaire, head to Italy. Two-time Oscar winner George Clooney has a busy work schedule, but he still finds time to relax there with his wife, Amal. The couple owns several homes, including two luxury villas in Lake Como, Italy: Villa Oleandra and the adjoining Villa Margherita.

Clooney, who has a net worth of $500 million, according to Celebrity Net Worth, spends up to four months a year at the lakeside Villa Oleandra. He purchased the property for $10 million in 2001, according to the Daily Mail. It was recently rumored that Clooney would be selling this property for over $100 million, but he has since denied the claims. 

Sting’s net worth is $550 million, according to Celebrity Net Worth, so it’s only fitting that the Grammy winner and his wife Trudie Styler own a Tuscan villa. The couple purchased the 900-acre Villa Palagio — located 16 miles from Florence, Italy — in 1997.

When the “If You Love Somebody Set Them Free” singer isn’t relaxing at his villa, he rents it out to the public. If you want to stay there, you’ll need to rent out the entire property.

While the luxury Tuscan estate can cost over $7,000 per week to rent, this didn’t prevent Kanye West and Bianca Censori from allegedly throwing all-night parties during their Italian vacation in 2023.

Long-time Malibu resident Cindy Crawford lives in a beach town, but that doesn’t stop her from heading to the ocean for vacations. Along with family friend George Clooney, the former supermodel and her husband Rande Gerber sold their Cabo San Lucas, Mexico, compound for $100 million in 2016, according to TMZ.

Justin Bieber and his supermodel wife, Hailey, have been spotted vacationing in Los Cabos annually. Nick Jonas even held a special birthday celebration for his wife Priyanka Chopra’s 40th birthday in town.

Incredibly, the extended Bush family — which boasts a combined net worth of $400 million, according to Celebrity Net Worth — includes two former presidents and a former Florida governor. Like many families, though, the group enjoys taking vacations together.

Located in Kennebunkport, Maine, Walker’s Point has been the family’s getaway for years. George H.W. Bush and his wife Barbara purchased a 26-room house on 11 acres of land from his aunt in the 1980s, and the family has since turned it into a compound.

In 2015, the former president and his wife built a brand-new house on the property for son Jeb and his family. Located on a 1.3-acre site worth at least $1.4 million, the 3,000-square-foot home cost $600,000, according to the Boston Globe.

A wintry playground for A-listers, Aspen is a favorite spot of Mariah Carey — i.e., the “queen of Christmas.” In fact, she spent time in a $22 million Aspen rental home, courtesy of Airbnb, during the 2016 holiday season. Known for top-notch ski resorts and luxury chalets, this is the ideal vacation spot for those who want the combination of gorgeous scenery and first-class amenities. 

Celebrities like Kurt Russel and Goldie Hawn have made Aspen their permanent residence. In 2022, the “Real Housewives of Beverly Hills” star Kyle Richards listed the Aspen residence that she owned with her husband, Mauricio Umansky, for $9.75 million. While the couple spent some time at the home, they had it available for $89,000 per month as a luxury rental.

The Indonesian island of Bali is a celebrity favorite. John Lennon and wife Chriss Teigan took their family on a vacation to the luxury resort Como Shambhala Estate, where rooms average around $540 a night. Other celebrities, like George Clooney, Demi Moore, Brad Pitt and Madonna, have been spotted vacationing on the island.

After leaving the White House, President Barack Obama checked in with his family to the Four Seasons Sayan, where they have a three-story palatial private pad.

The crown jewel of French Polynesia, Bora Bora frequently attracts A-list guests. The Kardashian family — along with Kim’s then-boyfriend Kris Humphries — vacationed at the Hilton Bora Bora Nui Resort in April 2011, and their trip was documented on their hit reality series “Keeping Up With the Kardashians.”

According to the Daily Mail, Four Seasons Bora Bora has welcomed a variety of celebrity guests, from Courtney Cox to Jimmy Kimmel. Guests are picked up from the airport on a private boat, but the highly private bungalows come with a steep cost. The average cost for a room at the resort ranges from $4,009 to $26,000.

Located off the east coast of Spain, Ibiza is a top destination for celebrities. Revered by the fashion crowd, the island played host to models Doutzen Kroes and Alessandra Ambrosio in 2017. Plus, it’s still cheaper to live in Ibiza than New York City, and Ibiza is only one of the many beautiful places in Spain.

Lionel Messi visits regularly and can be spotted tanning on his luxury yacht off the White Isle’s coast with his family. Rafael Nadal also co-owns a restaurant with friends on Mallorca and is known for visiting the White Isle in Ibiza. You may also be able to spot Beyoncé, Nicole Scherzinger or Elle Macpherson at the exclusive beach club Blue Marlin.

Who wouldn’t want to escape to one of the most beautiful beaches in the world? When he’s not traveling for work, Richard Branson, the Virgin Group founder — who is worth $3.6 billion, according to Forbes — heads to his private island in the British Virgin Islands.

Known for being a place where Branson and his celebrity pals can kick back and party, the island has hosted events ranging from Kate Moss’s 40th birthday party to the wedding of Google co-founder Larry Page. Branson bought Necker Island for $180,000 decades ago and has since turned it into a resort.

The all-inclusive property features a main house and six smaller houses, as well as pools, on-site dining, tennis courts and a disco DJ. Nightly rates vary by season, with rates for couples starting at around $5,650.

Martin Dasko contributed to the reporting for this article.