Inside the $4,500-a-night Hawaiian estate where the Obamas and celebrities like Angelina Jolie have vacationed

December 31, 2020

Inside the $4,500-a-night Hawaiian estate where the Obamas and celebrities like Angelina Jolie have vacationed

obama family hawaii vacation — President Barack Obama, Michelle Obama, Malia Obama, and Sasha Obama at the Honolulu Zoo in January 2009.
Kent Nishimura-Pool/Getty Images

During his presidency, Barack Obama usually spent the Christmas and New Year's holidays in Hawaii with his wife, Michelle, and their two daughters, Malia and Sasha.
For three years in a row, the Obama family stayed at a luxury vacation rental known as Paradise Point Estates, the estate's manager, Glenn Weinberg, told Business Insider.
Other high-profile guests who have stayed at the Oahu home include Ryan Reynolds and Blake Lively, Bradley Cooper, and Angelina Jolie and her sons, according to Weinberg.
Paradise Point Estates is open for anybody to book starting at $4,500 per night for a minimum seven-night stay — not including tax and a $1,000 cleaning fee.
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The Obamas have long escaped to Hawaii for their annual Christmas vacation - and this year was no exception.

In early December, former President Barack Obama was spotted playing golf in Hawaii while on his annual holiday vacation with his wife, Michelle.

During Obama's first term, the former president and his family typically returned each year to one vacation rental that became known as the "Winter White House." The Obamas spent the Christmas and New Year's holidays of 2008, 2009, and 2010 at a luxury vacation home known as Paradise Point Estates, the estate's manager, Glenn Weinberg, told Business Insider.

According to Weinberg, the Obamas inquired about staying each following year of his presidency, but Weinberg started using the home for his own family holidays starting in 2011.

Paradise Point Estates sits right on the beach and comes with a heated lagoon-style pool and pavilion with tropical waterfalls. Other high-profile guests have included Ryan Reynolds and Blake Lively, Bradley Cooper, and Angelina Jolie and her sons, Weinberg told Business Insider. (Their reps did not immediately respond to a request for comment.)

But the five-bedroom home isn't just for presidents and celebrities. It's available for anyone to book starting at $4,500 per night with a seven-night minimum stay - not including tax or a $1,000 cleaning fee.

Take a look inside Paradise Point Estates.

The Obamas have long spent their Christmas and New Year's holidays in President Obama's birthplace of Hawaii.

While vacationing in Hawaii during his presidency, Obama was often spotted at Oahu's golf courses, and the family could be seen on outings to the beach and to get shaved ice.

For three years in a row during Obama's first term, the family spent their winter holidays at the same vacation home: a secluded beach house in Kailua, Hawaii known as the Paradise Point Estates.

obama hawaii vacation house — Paradise Point Estates

According to the estate's manager, Glenn Weinberg, the Obamas spent the Christmas and New Year's holidays of 2008, 2009, and 2010 at Paradise Point Estates, which was also nicknamed the "Winter White House."

The Obamas also inquired about staying at Paradise Points Estates in the following year, Weinberg said, but starting in 2011 Weinberg used the home with his own family over the winter holidays.

According to Weinberg, President Obama once wrote in the property's guest book: "My family and staff have grown very fond of our time at your home, and your generosity is much appreciated."

A spokesperson for the Obamas' nonprofit organization did not immediately respond to Business Insider's request for comment for this story.

Paradise Point Estates is a plantation-style, single-level home with five bedrooms and 5.5 bathrooms.

The nearly 5,000-square-foot house is surrounded by lush foliage and palm trees.

The vacation rental is steps from Kailua Beach, a 2.5-mile stretch of pristine sand that's considered one of the most beautiful beaches on Oahu.

Source: Best of Oahu

A night's stay at the Paradise Points Estates starts at $4,500, with a required seven-night minimum stay.

That doesn't include Hawaii state tax and a $1,000 cleaning fee. A minimum $10,000 security deposit is also required, although Weinberg said he's never had to keep any part of a guest's security deposit.

To request to book the property, guests must fill out a rental inquiry from.

The home's expansive great room has vaulted ceilings and opens up to the outdoor living areas.

Source: Paradise Point Estates

The living area is adjacent to the home's gourmet kitchen, which comes with a wine fridge, multiple coffee makers, ice makers, and two dishwashers.

Guests often have private chefs prepare their meals in the kitchen, Weinberg said.

There's also a spacious formal dining area.

Source: Paradise Point Estates

The spacious master suite includes a chaise lounge, a sofa, a writing desk, and a walk-in closet.

The master bathroom has a steam shower and a deep soaking tub with views of the water.

Source: Paradise Point Estates

The master suite is situated to have the best view of Kailua Beach and the sunrise.

Source: Paradise Point Estates

Outside is a private patio with lounge chairs looking toward the ocean.

In addition to the master suite, the home has a guest suite and three other guest bedrooms.

The house also has a home theater and a fitness center.

The home gym is equipped with a treadmill, elliptical, stationary bike, Summit Climber, Smith Machine, a dumbbell rack, hand towels, and a refrigerator.

The vacation rental showcases the Hawaiian outdoor-indoor lifestyle, according to the property's website.

Source: Paradise Point Estates

The centerpiece of the property is a courtyard with a heated, lagoon-style swimming pool.

Source: Paradise Point Estates

Elevated slightly above the pool is a hot tub with tropical waterfalls.

In the pool pavilion, guests can also enjoy a pool bar with an ice maker, a TV, and a gas grill.

Throughout the courtyard are several "lanais," the Hawaiian term for a covered outdoor patio.

Guests staying at Paradise Point Estates have access to a complimentary concierge service to help with restaurant reservations, golf club reservations, or suggestions for activities.

They also have the option to book a private in-home massage or private chef.

Beyond the prime beachside location and resort-like amenities, it may also have been the security features that drew the Obama family to Paradise Point Estates.

According to Weinberg, the home is equipped with "celebrity-level" security.

For one, its sits in a gated community. Upon arrival, guests step out of their cars into a private motor court. And the property has a zoned alarm system and a six-foot fence on all non-ocean view sides.

There's also a "state-of-the-art" security system with cameras around the property, Weinberg said.

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