Even though the president and his family do not have any public events scheduled, locals are hopeful.
At Island Snow, an ice cream shop where Obama and his daughters showed up last year, owners have added his order to the menu under the moniker, "Snowbama," a tasty combination of guava orange, lemon lime and cherry, the three flavors Obama ordered.
"Everybody saw that picture. So everybody wanted to know what kind of shave ice he got, where he sat when he ate it, how he acted when he came and got it. So the curiosity factor was very high," manager Free Arndt told ABC News.
"A lot of people are like, yeah, he's coming back, he's coming back, gotta be ready for him," he added.
Some locals are complaining that the Obamas presence will be bad for business. Flight companies were worried that they would be grounded for the first family's Hawaii trip.
But David Earles, a member of the Kailua Chamber of Commerce, said in the long term, Obamas' will help the island.
"You could never ask for a better spokesman than what we've got in the president of the United States showing up here with his family," Earles told ABC News. "We certainly anticipate this is gonna bring a lot more people down the road just because of the fact that the president's been here."
Keika Albarado, owner of gift shop Buti Grove, said business has picked up in anticipation of the Obamas' arrival, especially merchandise that has anything to do with the first family.
"Anything with his face on it that says Hawaii," Albarado told ABC News. "I think his visits definitely boost the tourist industry."
Obama himself has a personal connection to this stretch of sand.
"His grandfather used to take him to Kailua beach because it's a great swimming beach," said Dave Zimel, owner of Paradise Points Estates. "So President Obama, I think, he probably learned to swim right out here."
It remains to be seen whether the public will see the president swimming in the ocean on this trip. Pictures of the president and his family in bathing suits caused quite a stir last year.
The beach outside Obamas' rental is world renowned -- it has been ranked the island's best and was a favorite of Hawaiian royalty -- but with so many prying eyes, this year the Obamas and their friends and family may just be relaxing indoors.
That might not be such a bad idea.
The $8.9 million vacation home -- which costs around $4,000 a night -- boasts a pool and breathtaking views.
ABC News' Jon Garcia contributed to this report.