A presidential retreat in Kailua, Hawaii

The Obama family has rented the Plantation Estate, a 5,000-square-foot with five bedrooms, on Oahu.

The Obama family has rented the Plantation Estate, a 5,000-square-foot with five bedrooms, on Oahu.

(Beverly Beyette / For The Times)
Special to the Los Angeles Times

This laid-back beach town 12 miles northeast of Honolulu on windward Oahu has no hotels — which is just fine with the locals — but it can boast of being home to what some call the “winter White House.” Kailua hosted the vacationing Obamas in December and on two previous occasions. Most residents are just fine with that too, despite the disruptions caused by the arrival of the presidential entourage.

On a recent day I toured the Plantation Estate, which the Obamas leased in December 2008 and again last December. If it’s not paradise, it’s close: A perfect green lawn slopes down to the white sand and turquoise water of beautiful Kailua Beach, and a very private lagoon pool and a presidential suite with king bed and sliding glass doors open onto sweeping views of the beach, bay and Mokulua Islands.

The estate, in a complex of three homes, is exquisitely furnished. It has an open-plan living room, dining room and kitchen; a media room, travertine and African mahogany floors; and state-of-the-art kitchen. A shaded poolside lanai has a built-in flat-screen TV, a favorite after-swim retreat of the Obama girls, Sasha and Malia.

The 5,000-square-foot property, recently sold to Glenn Weinberg of Baltimore for $6.9 million, has five bedrooms and four outdoor entertaining areas, and it’s available to just plain folks for $3,500 to $6,000 a night, depending on the season and length of stay. (The minimum is a week.) The Obamas paid their own way, property manager Allison Pettersson said.


On Kailuana Place, a cul-de-sac with a guard house and a “no trespassing” sign, it was a happy choice for the Secret Service (who operated out of one of the bedrooms). Part of the beach was blocked off during the Obamas’ stay.

The president, who grew up in Honolulu, has longtime ties to Kailua (population 50,000), where his grandparents once lived. In his 1995 memoir, “Dreams From My Father: A Story of Race and Inheritance,” he recalled spearfishing with his grandfather in Kailua Bay.

Kailua is about a 30-minute drive from Honolulu over the Pali Highway — and light-years away. “Basically, this is country,” said Herman Allerstorfer, who was behind the desk recently at the Kailua Information Center downtown. “Young people are more comfortable in Honolulu.”

Favorite local hangouts include Teddy’s Bigger Burgers, with its ‘50s theme, and Buzz’s, an indoor-outdoor steakhouse and 48-year institution.

Lucy’s Grill & Bar, with bare tabletops, surfboards on the walls and a menu with ethnic influences — Hawaiian, Asian, Indian — was Barack and Michelle Obama’s pick one night for dinner. I, too, ate there, choosing the dinner-sized appetizer of spicy Balinese chicken in a butter lettuce cup with peanut and mint sauces for $11.

Sasha and Malia were partial to Island Snow, which dishes up shave ice — up to three flavors plus a scoop of ice cream — for $2.75. “The president has been here twice,” said manager Richard Whaley, “and the girls four or five times.” (For the record, the president favored cherry-lemon-lime and guava-orange.) The logistics of such a visit are complicated.

“If he comes, the Secret Service shuts down everything within a mile radius,” Whaley said, “and every car in the parking lot is checked with bomb-sniffing dogs.

“It was good for us, but probably bad for everybody else.”


And Sasha and Malia were a big hit. “The little girls are cool,” Whaley said.

While in Kailua, all four Obamas acquired clothing from Muumuu Heaven, a super-chic boutique on Kailua Road. The co-owner, Deborah Mascia, is a friend of the president’s half-sister, Maya Soetoro-Ng, and Mascia did some original designs with Michelle Obama in mind. She bought a sleeveless, V-necked, long black bamboo gown ($245) and a halter-neck, long column gown in a brown print ‘60s fabric ($265).

The black gown has an inset belt of vintage fabric from a muumuu that belonged to the president’s grandmother, Madelyn Dunham, who died in 2008. Some of her muumuus were given to Mascia who, with her husband and shop co-owner, Eric, helped the family vacate Dunham’s apartment. The president also owns a cummerbund and matching bow tie made by Muumuu Heaven from one of his grandmother’s muumuus.

When the Obamas vacation in Kailua, it’s mostly about being with friends and family. The president was seen regularly at the fitness center at nearby Kaneohe Bay Marine Corps Base. For other visitors, it’s mostly about the beaches at Kailua and Lanikai bays for snorkeling, stand-up paddle boarding and kayaking, but there are a few sightseeing options.


Byodo-In Temple in Kaneohe is a replica of one in Uji, Japan. It has an impressive Buddha and a magnificent setting with the verdant, craggy mountains as a backdrop. It’s a peaceful place, with extensive koi ponds, swans and peacocks.

Close to the center of Kailua is Ulupo Heiau, the remains of a temple once 140 by 180 feet with 30-foot-high walls, which was a sacred site for early Polynesians who are believed to have conducted rituals here seeking blessings such as a bountiful crop. Some still consider the site sacred; the day I visited, a fresh orchid lei had been placed over the temple site marker.

On a ridge overlooking neighboring Lanikai are the remains of abandoned pillboxes installed when there was a threat of Japanese invasion. With its sweeping views, the site is said to be a favorite place for marriage proposals. It’s a steep uphill hike.

The town is a down-home kind of place, where everybody seems to know everybody, people in shops and restaurants are friendly and you just get the idea that they’re happy living here. The Thursday night farmers market at Kailua Town Center is a traditional gathering spot. Several artists call Kailua home, and one happy consequence is the Art in Public Places project. Strolling on Kailua Road, the main artery through the business district, you may pass a mosaic of canoers or a bronze sculpture of a beach girl.


The Kailua area is no stranger to the rich and famous. Paul Mitchell, the late Scottish-born hair products king, fled New York in the ‘70s and moved to Hawaii, where his first home was a $450-a-month beach cottage. Here in Hawaii, he made a fortune in hair care and built several homes, including one in Lanikai, Kailua’s neighboring town. I visited the complex of seven structures on 1.3 beachfront acres.

This seven-bedroom and nine-bath place is available for $35,000 to $53,800 a week ( The woods are exquisite, including hand-carved teak doors from Bali and a spiral staircase from wood from a monkey pod tree on the property.

Although there is no hotel, bed-and-breakfasts abound in Kailua and Lanikai, “some legal, some illegal,” said Allerstorfer, whose family has three vacation rentals (

The Obamas have not rebooked the Plantation Estate (, Weinberg said. Would he like to have them again as tenants? Oh, yes. “I’d like to rent to anyone who’d pay the rent, including them.”


For information: Kailua Information Center, 600 Kailua Road, Oahu; (808) 261-2727,