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

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.

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.