Culture / Travel

Inside an Austin Billionaire’s Lavish Hawaii Resort Wonderland — Your Guide to Hualalai

Four Seasons Hotel, Celebrity Adored Homes and Aloha Spirit Bring Oceanside Thrills

photography Hualalai Resort

“If you could go anywhere in the world for your next vacation, where would it be?”

During an oceanside dinner at the impeccable Hawaiian island resort of Hualalai, it is not unordinary to overhear a family in deep conversation discussing their ideal destinations over fresh seafood — the latest five-star awarded hotels in Italy or the Isle of France, or the highly acclaimed safari site in Tanzania, or perhaps the boundary-pushing wellness hideaways in the depths of Asia. The names mentioned are amongst the most above and beyond properties, the creme de la creme in vacation options.

One such family had sharp and educated arguments for their choices. This family was not only well-traveled, but understood the meaning of authentic luxury.

This family represents the quintessential visitor of Hualalai, the lavish oceanfront resort community spanning 865 acres, located on the exclusive Kona-Kohala coast of the Hawaii Island.

Now owned by Austin billionaire Michael Dell’s MSD Hospitality, the amenity-filled residential resort with award-winning golf courses, spas, restaurants and state-of-the-art facilities and programming boasts vacation dream homes, villas and the lauded Four Seasons Resort Hualālai.

Golf Course Haualalai (Photo by Hualalai Resort)
Hualalai boasts two famous golf courses that attract the biggest names in the sport. (Photo by Hualalai Resort)

The property is a magnet for the global traveler and some of the highest profile names in business. Homeowners include Citadel founder Ken Griffin, Columbia Sportswear CEO Tim Boyle, Charles Schwab and Howard Schultz, not to mention other countless noteworthy names including Lebron James and Jay Z and Beyoncé that have graced that gates for a hotel stay or home rental.


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These icons no doubt fell in love with the low-key, casually elegant luxury that this billionaire’s paradise touts.

“They either don’t know who I am or don’t give a shit,” says one billionaire homeowner.

The focus is on the precise and doting service, a generous and welcoming “Aloha Spirit,” and the advanced amenities. It is not about flash.

Hualālai Homes

Visitors yearning to extend their stay beyond the hotel can seek ownership of coveted Hualālai real estate.

Luxury vacation real estate aficionado Rob Kildow leads the charge in helping the discerning homeowners fall in love with the property and the buying opportunities including custom homes, home sites and villas.

Options range from a two- or three-bedroom condo style villa for around $1.4 million to five bedroom custom homes for $14 million and beyond.

A large percentage of real estate sales are from already existing homeowners who fall in love with the resort so much that an expansion or upgrade is needed. 

Homeownership buys an exclusive Hualālai Club Membership that offers access to two 18-hole championship golf courses designed by legends of the game, Jack Nicklaus and Tom Weiskopf, each with its own clubhouse, the award-winning Hualālai Sports and Tennis Club, Hualālai Spa, the Hualālai Canoe Club, and the oceanfront Residents’ Beach House.

Membership also provides access to all amenities at Four Seasons Hualālai Resort, including the beach and pools and stellar dining spots — all just a golf cart ride away.

If the expertly designed homes all with perfect vacation features like outdoor showers, enormous Lanai patios ideal for entertaining, or sliding glass walls for seamless indoor/outdoor living won’t seal the sale, the views will.

The entire resort was designed specifically so that each property has a view of the brilliant band of ocean combined with the sparkling white sand beaches and black lava landscape.

Four Seasons Resort

The Four Seasons Resort at Hualālai has continued to be one of the top-performing hotels in the brand’s portfolio year-over-year and sets a high standard standard for exceptional service.

The 243 rooms, divided into quaint sections of two-story bungalows carved into island lava rock, each boast their own uniquely spectacular view of the ocean and natural sound machine of crashing ocean waves just a few yards away.

Catering to all varieties of affluent travelers, with different “neighborhoods” of rooms, including rooms surrounding the lively pools for families, more quiet enclaves of rooms fit for honeymooners or incredibly private villas and suites for high profile guests, the property tailor-curates each guests experience down to the room location.

Four Seasons Haualalai (Photo by Hualalai Resort)
The Four Seasons sits perched upon the sparkling white sand beaches allowing for a complimentary sound machine of crashing ocean waves. (Photo by Hualalai Resort)

The spread-out resort offering amenities and activities to meet every whim sets the standard for attention to detail and one-on-one service that complements the guests’ well-curated experience.

The five dining destinations have carefully crafted menus with gourmet food using fresh ingredients from the jsland and exceptional service.

Expect staffers like Lilibet at ‘Ulu Oceanside Grill to give you knowledgable menu and wine pairings off the cuff to make you feel like you’re the most VIP guest in the room.

The newly renovated spa offers extravagant services drawing from ancient Hawaiian wellness principles such as scrubs with sandalwood harvested just a few miles away and wellness walks through a finely landscaped garden to facilitate full inner peace.

There are family pools, lively adult pools complete with swim up bar, quiet pools, beachfront lounge areas, water activity docks and even a brackish water pond for up-close-and-personal snorkeling to see more than 3,000 species of fish and marine life.

Enjoy all of this with doting attendants bringing your fresh-made popsicles, aloe vera, phone chargers and even pool side concierge services.

The resort’s renowned multi-million dollar art collection will set the tone for the type of true extravagance that vacationers appreciate. The distinctive collection that pervades the property, from the lobby to the ballroom foyer to the restaurants and guests suites add to the divine surroundings that give the hotel its luxury feel.

Resort events that keep the property on the map include the Mitsubishi Electric PGA Tournament that happens each January, bringing big golf names to the sought after golf facilities.

The Four Seasons Chef Fest brings leading industry chefs and affluent foodies to the resort. The one-of-a-kind dinners inspired by the island and cooking classes based on the sustainably grown food resources on the property make for a foodie dream trip.

Hawaii’s Aloha Spirit

Few things carry as much happy mystique as Hawaii’s “Aloha Spirit.” The charm, warmth and sincerity of Hawaiians is legendary — and this luxury enclave works to protect it.

The resort’s Natural Resources Team of scientists and ecologists are dedicated to preserving the unique wildlife in the 14 ponds and surrounding natural areas on the property, in addition to cultivating their own shrimp, oysters and home-grown native vegetables for farm-to-table meals.

The team even offers programs for guests of all ages to learn more about the natural habitat and the Hawaiian principles of sustainability that place such an importance on the resorts ecosystem.

The Cultural Center, curated by the Cultural Ambassador nicknamed Uncle Earl, keeps resort guests in tune with the sacred history of the land. The center honors local customs and traditions withukulele lessons, lei making and countless other offerings.

As Uncle Earl says, “You cant teach Aloha, it is meant to be shared.”

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