14 ultra successful people who call Hawaii home (Part 2)

Wealth, fame, a house in Hawaii — not a bad plan if you can swing it. That’s exactly what many of elite do: they buy a private, usually oceanfront, property on their favorite Hawaiian island and steal away from their busy international lives to relax and recharge.

In Part 2, we reveal the who’s who on Maui, Kauai, and Lanai. Part 1 is all about Oahu and the Big Island. Enjoy!


Jeff Bezos

Amazon.com founder, space tourism entrepreneur at Blue Origin, and sometimes the world’s richest person (currently #2). Mr. Bezos recently bought a 14-acre property near La Pérouse Bay in Makena on Maui’s south shore.

Clint Eastwood

Legendary actor (“Dirty Harry,” among others), Oscar-winning director, and former mayor of Carmel, California. Owns an oceanfront house in Wailea in an undeveloped area knows as White Rock, near the Polo Beach Condos.

Mick Fleetwood

Founding member of Fleetwood Mac. Mick’s house is near Napili Bay, but you’re more likely to see him at “Fleetwood’s on Front Street,” his popular restaurant in Lahaina.

Woody Harrelson

Activist, vegan, and actor known for his roles in Natural Born Killers, Hunger Games, Zombieland, and the 80’s sitcom Cheers. Mr. Harrelson owns 2 properties on Maui — on the north and east sides, where he’s known to host infamous celebrity poker games.

Willie Nelson

Country music legend and environmentalist. Mr. Nelson owns a home in Paia, where he also has raised a family. His son Lukas, who grew up on Maui, is also a musician, and plays occasionally on island — sometimes with his dad. Willie Nelson has also played with Jack Johnson at Jack’s “Kokua Fest” on Oahu.

Stephen Tyler

Aerosmith front man with an unmistakable voice. Makena is where this rock n’ roll legend owns his home, set on a 1/4 acre with the ocean on one side and a natural preserve on the other. Not too shabby.

Oprah Winfrey

Media queen and mogul billionaire. Oprah owns a massive ranch on the slopes of Haleakala near Kula. She helped to commission a private road that starts in Wailea and ends in Keokea near her property, which saves all that time from going upcountry to Kihei through Central Maui.


Pierce Brosnan

Actor, best known as James Bond, Remington Steele, and Sam Carmichael from Mamma Mia. Now he’s a SUP dad who spends a great deal of time on Kauai’s North Shore near Tunnels Beach at Hā‘ena Point. He claims he feels most at home in the islands.

Steve Case

Founder of AOL and venture capitalist. Hawaii born and raised, Mr. Case bought Grove Farms in 2000, and also bought nearly 20,000 acres of former Lihuʻe Plantation lands.

Laird Hamilton

Big wave surfer, athlete, and entrepreneur. Laird is a local boy who grew up on the North Shore of Oahu surfing some of the world’s most challenging waves. Now he splits his time between Malibu and the north shore of Kauai with his wife Gabby Reece and their children.

Bette Midler

Legendary actress and singer from films like Big Business, Beaches, and Hocus Pocus. Ms. Midler grew up on Oahu and owns a home in Kilauea, along with some other parcels of land on the island.

Ben Stiller

Comedic actor from such films as Meet the Parents, Tropic Thunder, The Secret Life of Walter Mitty, and many more. Stiller’s home is in Kilauea, above Kalihiwai Bay on the end towards Secret Beach.

Mark Zuckerberg

Facebook/Meta founder. Mark Zuckerberg and his wife Priscilla have purchased over 1,400 acres on Kaua’i’s north shore, which cover portions of the Pila’a, Waipake and Lepeuli ahupua’a (traditional Hawaiian land division). Their house is on Ko’olau Ranch, which is home to sustainable ranching and farming operations.


Larry Ellison

Founder of Oracle. Mr. Ellison actually owns 98% of The Pineapple Island, which he bought for $300 million. Lanai is 90,000 acres and home to around 3,000 people, some of whom work at one of Larry’s 2 Four Seasons resorts.

Need a hand with your next Maui vacation? Please contact the Sunny Maui Vacations team at info@sunnymauivacations.com or call 808-240-1311, ext. 21. We’ll find you the best vacation rental condo or rental home in South Maui and help you with any and all recommendations and activities across Maui.

Image credits: Wikipedia, bishoff, 21438530@N03, globalsportsforum, montclairfilmfest, Scott Beale / Laughing Squid

Need a hand with your next Maui vacation? Please contact the Sunny Maui Vacations team at info@sunnymauivacations.com or call 808-240-1311, ext. 21. We’ll find you the best vacation rental condo or rental home in South Maui and help you with any and all recommendations and activities across Maui.