Hillary Rodham Clinton has a speech planned at an old whaling church in need of fixing up and Mr. Clinton plans a round of golf.
Both will attend fund-raisers for an Irish-American charity and for the first lady's possible Senate bid in New York.
There are six fund-raisers for the first lady over the next two weeks, reports CBS White House Correspondent Bill Plante.
This is the fifth Vineyard vacation for the Clintons. They will spend nine days on the 20-acre Oyster Pond estate of developer Richard Friedman, their host for the past three years.
On Aug. 28, the Clintons leave the Vineyard to go to East Hampton, N.Y., where they will take part in a Democratic National Committee weekend retreat and other events to help raise money for Democratic candidates. On Aug. 30, they travel to Skaneateles in upstate New York, returning to Washington at the start of the Labor Day weekend.
The first family kicked off their vacation with a birthday party for the president at the home of Vernon Jordan. Aides say the president received numerous birthday wishes from friends and officials, including a congratulatory telegram from Boris Yeltsin, reports CBS station WBZ-TV in Boston.
Last year when the Clintons came to MarthaÂ's Vineyard for vacation, it was at the low point of the presidentÂ's personal and political fortunes.
On Aug. 17 last year, the president testified before a grand jury then admitted that he lied to his family and the nation about his affair with Monica Lewinsky.
A day later, the visibly strained family, linked by daughter Chelsea, took off for a vacation on which Mr. Clinton was almost invisible.
A year later, Mr. Clinton has survived impeachment, and the first lady is carving out her own political career. Arriving for this vacation, the first family Â— led by the presidentÂ's dog Buddy Â— seemed ready to relax.