Every summer the Vineyard, as it's known to locals, serves as summer haven for a bevy of well-known, well-heeled celebs, offering the president and his brood the chance to sip coffee with the likes of Meg Ryan, spend a day at the beach next to "Cheers" alums Ted Danson and Woody Harrelson, or even play a round of golf with his predecessor, President Bill Clinton.
"If the Obamas are so inclined, the likelihood that they could mingle with a few celebrities while they're on the island is very high," said Dawn Bellante-Holand, the general manager of Martha's Vineyard Online, MVOL.com.
According to island insiders, the family is likely to get invites to several of the many star-studded functions that take place on the island every summer.
"There is a very active social scene here," said Bellante-Holand. "There are lots of cultural events and gatherings and fun activities to do with kids that really bring people out."
Bellante-Holand said that the island's summer season is in full swing -- last week was the vastly popular Agricultural County Fair that is known to attract celebrities such as Reese Witherspoon and her beau Jake Gyllenhaal, along with Witherspoon's two children. Gyllenhaal and his sister Maggie have been long-time residents of the island.
Obama's Martha's Vineyard Vacation Spot a Big Draw for Celebs
Academy Award-nominated actress Diane Lane and fellow screen star Meg Ryan are also frequently spotted taking advantage of the island's activities.
"At any given time you can see Ryan at one of the breakfast places in nearby Edgartown for coffee and breakfast," said Kim Wells, the publisher of Vineyard Style magazine. "It's not like they can hide in their houses -- how could you?"
And if the president is in the mood to hit the links, he need not look farther than the Emmy-winning Woody Harrelson, who Wells saw teeing off on an island golf course just last week.
"The Obamas are likely to be in the company of some pretty big stars," said Wells. "The summers here are definitely star-studded."
Dan Aykroyd, Bill Murray and notable film producers Peter and Bobby Farrelly are also island regulars.
Danson and his wife Mary Steenburgen, considered one of the more active celebrity couples on the Vineyard, spend time on the island year-round and are never hard to find, according to Wells.
In addition to the rumor that avid Obama fan Oprah Winfrey may be summering on the island at the same time the Obamas visit, there are whispers around town about a secret, high-profile sailing trip, Wells said.
"I heard Carly Simon was going to be going sailing with the Obama family one day," she said. "That would be great."
Simon and her ex-husband and fellow musician James Taylor are both considered island fixtures, almost as much as the Brooklyn Dodger flag that actor and director Spike Lee flies above his estate in Oak Bluffs.
"He's very proud of that flag," Wells said.
Plenty of Politicos
And if the Obamas feel out of place among the Hollywood elite, fear not, there are plenty of Washington, D.C., regulars on the island, too.
Former President Clinton was spotted golfing last weekend, and the rest of his family is rumored to be in tow.
Speaker of the House Nancy Pelosi is also expected to visit this summer.
"The people who come here are very accomplished in whatever they decide to pursue," said Bellante-Holand of the eclectic mix of people who travel to the island. "That makes for some great chance meetings."
Martha's Vineyard Offers Safe Haven to President, Celebs
So what does the Vineyard offer these celebrities who remain loyal to the island year after year?
Despite the opportunity to stalk your favorite celebrity, locals on the island really respect the stars' space, said Bellante-Holand.
"Everyone here tries to value the privacy of the people who visit here, and that's one of the reasons it's such a popular vacation spot for stars," she said. "It makes it very easy to enjoy themselves and enjoy their friends or family who come with them."
Nancy Gardella, the executive director of the Martha's Vineyard Chamber of Commerce, says that it's the escape from the lens of intrusive photographers that makes Martha's Vineyard so appealing.
"They can move around and be themselves and people are pretty laid back," she said. "They can have a real family vacation without having to worry about being chased down by paparazzi."
As for the stars that Malia and Sasha Obama might like to see, there's no word yet on the chance of a Jonas Brothers sighting.