10 Celebrities Living the Hawaii Life

Drawn to the world-famous beaches and secluded hideaways, these VIPs — including Obama, Oprah, and Rihanna — love to escape the red carpet for Hawaii’s island paradise. Take a look inside these exclusive residences with million-dollar ocean views, sprawling beachfront grounds and floor-to-ceiling star appeal.

By: Kathleen Rellihan
Show: Hawaii Life
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Photo By: Paradise Point Estates

Photo By: Paradise Point Estates

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Photo By: Hilton & Hyland, a member of Luxury Portfolio International

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Obama's Winter White House

Hawaii’s most famous local? President Obama, of course. The President spent his annual winter vacations with his family at Paradise Point Estates in Kailua Bay Beach, the same beach he would visit as a child growing up in Oahu. A world away from Washington, DC, the 44th president and his family unwind in the secluded, heated, lagoon-style pool, complete with lava rocks and waterfalls. 

Obama's Winter White House

The First Family’s luxury beachfront rental features a gourmet kitchen, fitness center, oceanfront lanais and secure lava-wall-fenced grounds. 

Emma Stone’s Diamond Head Villa on Oahu

While filming Aloha, Emma Stone rented this multi-million dollar villa on the base of Diamond Head that starts at $4000 a night. Natural stone and wood details are featured in this high-tech home that is fully controlled by wall-mounted iPads. And perfect for the Hollywood set, the Oahu villa includes a private movie theater. 

Emma Stone’s Diamond Head Villa on Oahu

Thanks to this home's emphasis on indoor-outdoor living, VIP vacationers spend their days and nights watching the waves break or the sun set in the heated pool or lounging in the poolside cabana, complete with large flat screen TV. 

Oprah’s Farmhouse on Maui

The talk show queen’s remote ranch sits at almost 4,000 feet above sea level on the side of Mount Haleakala on Maui. The self-made billionaire owns approximately 780 acres on the Hawaii island.

Oprah’s Farmhouse on Maui

With fond memories of growing up on a farm on Mississippi, Oprah turned 16 acres of her Hawaiian estate into a working farm that produces 145 pounds of food each week. She donates the produce grown on her farm to the local community. We can almost picture the media mogul rocking on her farmhouse’s wraparound porch after spending a day picking turnips. Almost. 

Julia Roberts' $30M Kauai Estate

Hollywood darling Julia Roberts recently put her beachfront estate in Hawaii on the market for nearly $30 million. The Oscar-winning actress’s two-acre property is located on Kauai’s sought-after North Shore, a celebrity favorite with beachfront homes in the median of $1 million. Buy this property and you might run into some famous neighbors like Chuck Norris and Facebook’s Mark Zuckerberg.

Julia Roberts' $30M Kauai Estate

The 3,792-square-foot home sits on the famed Hanalei Bay, with 200 feet of beachfront. The property, known as “The Faye Estate” for the sugar plantation manager who bought it in 1915, is one of the only original large estates on Hanalei Bay that hasn’t been subdivided. 

Beyonce and Jay Z’s Hawaiian Haven

This Hollywood power couple kicks back in a private estate on Kailua, in the same neighborhood where President Obama vacations. This 15,000-square-foot-plus home sits on 1.5 lush acres with a rock-lined pool. With eight bedrooms and 11 baths, Beyonce and Jay Z can invite a few friends over, too. (Perhaps for a movie night — the home’s private theater includes stadium seating.) 

Beyonce and Jay Z’s Hawaiian Haven

In addition to Beyonce and Jay Z, this celebrity-favorite has served as a vacation home for Jessica Simpson, and Eddie Vedder of Pearl Jam was married on the property. The private Hawaiian estate offers 600 feet of white sand beachfront, and natural rock wall landscaping provides privacy from the peering paparazzi. 

Rihanna’s Luxe Vacation Pad on Oahu

Taking a break after lots of “work, work, work” on her latest hit, the pop diva decompressed in Paul Mitchell’s estate on Oahu, which rents for $6000 a night. The Hollywood hairdresser’s super luxe estate is set on an acre of coveted oceanfront in Kailua with breathtaking views of the Mokulua Islands.

Rihanna’s Luxe Vacation Pad on Oahu

Paul Mitchell’s coconut-tree lined estate includes tropical gardens, a Japanese bath house, a salt water lagoon, stone fire pit with lave benches, and a secluded beach cove, perfect for high-profile guests like RiRi. For the full star treatment, the property also provides a personal concierge service.

Neil Young’s Hideaway on Big Island

“Old man look at my life” on the Big Island and be pretty jealous, croons Neil Young. For $20 million, the singer-songwriter sold his secluded estate that sits between two bays and right off a popular surf break and white-sand beach. 

Neil Young’s Hideaway on Big Island

The two-time Rock and Roll Hall of Famer’s former island retreat includes over 800 feet of rock-strewn oceanfront, a five-bedroom beach house, two guest cottages, two green houses, and a swimming pool with pool house. 

Terry Bradshaw's Big Island Estate

The NFL Hall of Famer scored $2.7 million for his 12-acre estate on the Big Island. The Hawaiian property includes a waterfall, two koi ponds, and a lap pool surrounded by stunning ocean and mountain views. 

Terry Bradshaw's Big Island Estate

The pro football star’s former house has four bedrooms, four and a half baths, a great room, and a dining room/kitchen that open onto a spacious lanai. And perfect for entertaining, the estate also has a guesthouse with its own private lanai. 

Frank Lloyd Wright's Hawaiian Home

Frank Lloyd Wright designed this half-moon shaped Hawaiian home to offer panoramic views of the Big Island’s ocean and volcanoes. In the architect’s signature  “organic architecture” style, the home has rounded walls made of coral aggregate block from Oahu and floor-to-ceiling windows along the entire span of the house.  

Frank Lloyd Wright's Hawaiian Home

This architectural wonder is full of seating areas indoors and out, perfect for admiring the island’s sprawling lush landscapes. There’s even a small soccer field on the estate’s property. For $891 a night, you can rent this historic Frank Lloyd Wright property in paradise.

Kareem Abdul-Jabbar High-End Home on Kauai

One of the benefits of buying a custom-built home for a NBA star? Vaulted ceilings and extra-high doorways. Basketball legend Kareem Abdul-Jabbar’s ocean-view home rests on more than 3 acres on Kauai’s famed North Shore. 

Kareem Abdul-Jabbar High-End Home on Kauai

The 6,000-square-foot island retreat sits on a bluff and has access to Kauapea Beach, known as Secret Beach for its seclusion. The estate includes a fruit orchard, a guest carriage house, and while there is no basketball court there is a tennis court on the property.