His sojourns have, without question, put this laid-back beach town on the map. Property values have soared here and in neighboring Lanikai, where the president likes to play golf. Chinese buyers now pop into local real estate offices inquiring about houses in "the president's neighborhood." And to the annoyance of residents, tourists wheel through the streets on fat-tired bikes snapping pictures of the Obamas' vacation rentals.
But in the hours before the first family arrived around midnight Friday, it was quiet on Kailuana Place, an unassuming street where the president's backyard opens to the turquoise waves of Kailua Bay and views of the peninsula that houses the nearby Marine base. At his last news conference of the year at the White House, Obama said he was looking forward to skipping town for "a couple of days of sleep and sun," and his Hawaiian neighbors seemed content to give him the privacy to do just that.
"I pity the guy that he's had such an adversarial Congress with the Republicans," said Doug Miller, a retired Honolulu police officer who lives up the street from the house that the Obamas are renting this year. "If he came up with a cure for cancer, they would somehow be against it."
Miller, who was in his front yard Friday steering his family's pet tortoise, Petrie, away from chewing the Christmas light cords, had already put out his Obama Chia Head, which was sprouting green tendrils of hair, and said he planned to put up a sign inviting the president to come by for a beer.
After the shaky rollout of his new healthcare law, Miller said Obama needed a real break: "It's unfortunate that there's been so many glitches — that's not his fault — it's a monster for him to unfold that kind of a thing. So I'm OK with him staying here despite the significant inconvenience that it does cause the neighborhood."
Those headaches were set to begin this weekend, first with the 24-hour parking ban on the streets around his house and later with the movements of the president's motorcade, which residents say can bring traffic on the two-lane roads of Kailua to a halt for as long as 45 minutes.
That is in part because of the intimacy of this small town, which curves along the southeast shore of the island about a 40-minute drive from the crowded beaches and shopping malls of Waikiki.
Separated from the bustling commerce of the south by a towering mountain range, Kailua and Lanikai were once unspoiled acres of farmland. Photos from the 1920s of the Kalapawai Market — a general store that sits in between Kailua Beach and Obama's favorite shave ice shop — show coconut plantations lining the ocean, and later watermelon and papaya farms that were established by Japanese immigrants.
Much of the home-building in these once-sleepy beach towns came after the construction of the Pali tunnels through the mountains, and residents have tried ever since to keep the development in check. Dash Holland, a real estate agent at Century 21 in Kailua, said the market here recovered faster than any other part of the island after the recession and "competition is fierce" for properties, particularly like the ones the Obamas have rented that look out on the ocean and the Mokulua Islands.
One property on Kailuana Place is listed for $4.9 million; another for $4.2 million. "We can't keep them in the magazines" because they sell so fast, she said.
Recently the Kailua Neighborhood Board went to battle with the state tourism agency, which was encouraging visitors on its website to seek rentals in Kailua if they could not find places to stay in Waikiki. Neighborhood board President Chuck Prentiss said only about 65 properties in Kailua can be rented legally, but hundreds are being advertised on websites like rental giants Airbnb and VRBO, which he said have no place in a residential neighborhood.
Prentiss, however, does not blame the president. "We like having him here," he said. "He's a local boy."
On each visit, the Obamas have done their best to blend in, spending much of their time at home and at low-key gatherings with friends. On Friday, Secret Service officers in striped short-sleeved shirts readied a small, white tent they will use while keeping watch over the Obamas' stretch of beach. On the street side of the house, black patrol boats were in place along the canal that runs beside Kailuana Place.
The Obamas' Christmas trimmings were spare: evergreen wreaths at either end of the driveway with small red bows. But before the family arrived, gardeners were busy in the front yard clearing palm fronds and trimming back the bushes blooming with tropical flowers.
If world events permit — moments after he landed Friday night, the president's vacation was interrupted for a briefing on the four servicemen injured in an attack in South Sudan — Obama is expected to frequent his favorite golf courses, work out at the Marine base, where he golfed on Saturday, and step out for hikes and shave ice with his daughters. Island Snow, which has doubled in size since they first visited, began serving the president's shave ice order — flavored with lemon-lime, cherry and guava syrup — as the "Snowbama" long ago.
Though Obama's visits are no longer a novelty, they still stir excitement here among some locals, including Henrick Vanryzin, a 41-year-old animator and illustrator who sells his handmade Tiki mugs (best known as the vehicle for mai tais) at a stand outside the Kalapawai Market.
"Growing up here, it's still surreal that he is from here," said Vanryzin. "Ninety percent of the kids I grew up with never left this island. I think it's good for the youth of Hawaii to see that you can succeed on the mainland."
Though he frequented the Baskin-Robbins where Obama once worked, Vanryzin said he'd never met the president, but would be keeping an eye out for the motorcade. "I've seen his hand," he said. "Twice."