The youngest child (hence, the nickname "Bebe" meaning "Baby" in Spanish) of Cuban immigrants to Tampa, Florida, Matias and Carmen, Rebozo owned several businesses in Florida, including a chain of coin laundry outlets, before starting his own bank, the Key Biscayne Bank & Trust, in Key Biscayne in 1964. Although of Cuban ancestry, Rebozo regularly attended Key Biscayne Presbyterian Church, sometimes accompanied in later years by Richard Nixon.
Rebozo first met then U.S. Representative Nixon in 1950 through Florida Representative George Smathers. Smathers had recommended Key Biscayne as a vacation destination to Nixon, who eventually set up the Florida White House in the area. While Nixon was vacationing in Key Biscayne, Smathers had Rebozo take Nixon deep sea fishing. Rebozo and Nixon then started a friendship that lasted 44 years.
In 1976, Rebozo was the subject of a bank fraud investigation. The loan application filed with Hudson Valley National Bank (Yonkers, New York), stated that the loan was for real estate when it was actually used as a business loan. Rebozo repaid the loan with interest, and the bank declined to file a complaint.