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If you’re wondering where former President Barack Obama is staying during his Hawaii vacations, you’ve come to the right place. As a frequent visitor to the Aloha State, Obama has a few preferred residences he stays at when soaking up the sun and taking in Hawaii’s natural beauty.

If you’re short on time, here’s a quick answer: Obama typically stays at a oceanfront rental property in the the Kailua area on Oahu’s windward side when visiting Hawaii.

Obama’s Main Hawaii Residence

Beautiful Kailua Oceanfront Rental Property

When visiting his native Hawaii, former President Barack Obama enjoys staying at a beautiful oceanfront rental property in the town of Kailua on Oahu’s windward coast. The 5 bedroom, 7.5 bathroom mansion sits right on Kailua Beach with incredible views of the turquoise waters.

With nearly 7,000 square feet of living space, the home provides ample room for the former First Family to relax and unwind in a tranquil setting.

Privacy and Security

The Kailua residence offers great privacy thanks to its location at the end of a quiet street. Large perimeter walls and Secret Service patrols also help keep away prying eyes. According to neighbors, the Obamas keep a low profile when staying there but occasionally venture out to popular Kailua spots like Buzz’s Steakhouse.

The location provides both seclusion and easy access to beach activities the family enjoys.

Location Near Popular Kailua Beach

The rental property lies just steps away from the world famous Kailua Beach, acclaimed for its soft white sand and calm waters. When not golfing or visiting friends, the Obamas spend time strolling along the shore, boogie boarding in the waves, picnicking on the beach, or simply watching spectacular Hawaiian sunsets.

The incredible beach access allows the family to embrace the Hawaiian beach lifestyle during stays on Oahu.

Obama’s Other Hawaii Stays

Luxury Homes in Honolulu

When not staying at his private residence in Kailua, former President Barack Obama has enjoyed stays at some of Honolulu’s most luxurious homes over the years. During Christmas vacations with his family, the Obamas rented multi-million dollar beachfront mansions in Lanikai and Kahala.

One property the family stayed at is a gorgeous 5-bedroom, 5.5-bathroom oceanfront estate valued at over $10 million. The home features a large infinity pool, tropical gardens, and unobstructed views of the calm turquoise waters.

With over 6,500 square feet of living space, it had plenty of room for the Obamas to relax and enjoy quality family time together.

Another magnificent mansion Barack and Michelle rented for 2 weeks had a staggering rental rate of $25,000 per night. Situated right on sandy white beaches, this sprawling property oozed luxury with amenities like a home theater, game room, and even a disc golf course!

Family Visits to B&Bs Nearby

In addition to Honolulu, the Obamas often spend time on the windward side of Oahu as well. The family has stated their affection for the laidback town of Kailua, where Barack’s sister Maya Soetoro-Ng resides.

When paying a visit to Maya, the former First Family would stay at cozy bed and breakfast inns nearby. Options like Lanikai Beach Rentals or Pat’s at Punalu’u give the Obamas a more low-key, local experience than the grand estates of Honolulu.

Many of these B&Bs are family-run establishments that have been housing guests for over 30 years. With amenities like free breakfasts and outdoor lanais, they allow the Obamas to relax and reconnect as a family, away from the glare of the public eye.

Visiting Obama’s Hawaii Hangouts

As a native of Hawaii, former President Barack Obama has several favorite spots he likes to visit when he’s back on the islands. Here’s a look at some of the places you might catch a glimpse of the 44th president if you’re lucky during your Hawaiian vacation.

Sandy Beach on Oahu’s East Shore

This picturesque beach park on Oahu’s east shore is said to be one of Obama’s favorite spots to bodysurf when he’s home. He’s been spotted riding the waves here on several occasions. The beach is popular with locals and visitors alike.

Rainbow Drive-In in Honolulu

This iconic Hawaiian plate lunch drive-in restaurant has been around since 1961 and is a go-to for Obama when he’s craving local grinds. He’s been seen waiting in line here on several occasions to order favorites like the mixed plate, loco moco, and chicken katsu.

Hanauma Bay Nature Preserve

This picturesque natural bay located on Oahu’s southeastern shore was designated a protected marine life conservation area in 1967. Obama has been spotted snorkeling here on vacation. The bay’s pristine waters and abundance of tropical fish make it a great place to swim and snorkel.

Alan Wong’s Restaurant in Honolulu

This award-winning restaurant that pioneered Hawaii regional cuisine has long been a favorite dining spot for Obama when he’s in town. He’s hosted several gatherings for family and friends here over the years.

Dishes like the soy-glazed butterfish and molten lava chocolate cake come highly recommended.

Kailua Beach Park on Oahu’s Windward Side

The Obamas have rented homes near this beach park on previous Hawaiian vacations. Its warm turquoise waters, white sand, and panoramic views make it an ideal spot for swimming, kayaking, standup paddleboarding and kiteboarding.

Obama is known to enjoy standup paddleboarding here when he’s on vacation.

So if you’re looking to potentially spot Obama when visiting Oahu, be sure to check out some of his long-time favorite spots around the island. With a little luck, you may just cross paths with Hawaii’s most famous resident.


As you can see, Obama has some prime oceanfront real estate he frequents when taking Hawaii holidays. While privacy and security are priorities, his main Kailua rental property provides beautiful views and access to a tranquil beach he enjoys visiting.

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