Candida endocarditis is a rare infection that is becoming an emerging and growing health concern, especially among risk groups such as the elderly and the immunosuppressed. It is associated with high morbidity and mortality. Dilemmas about Candida endocarditis treatment are still around, particularly about the treatment options and their duration. We report a case of Candida parapsilosis prosthetic valve endocarditis with septic embolisms. An elderly male patient with a biological prosthetic valve presented with fever and constitutional symptoms. Abdominal computed tomography (CT) showed an area suggestive of splenic emboli. Transesophageal echocardiography showed a vegetation attaching to the prosthetic valve. Due to several comorbidities, he was not considered a candidate for surgical treatment. He was treated with antifungal drugs (liposomal amphotericin B and caspofungin) and was discharged with per os fluconazole. Later he presented with evidence of lumbar spondylodiscitis due to septic embolization and relapsing fungemia with multidrug-resistant isolates was documented. Unfortunately, the patient outcome was ill-fated and he died in hospital due to sepsis-related to the candidemia and also nosocomial urinary sepsis. Here, we illustrate the complexity of diagnosing and managing fungal endocarditis due to its complications and poor prognosis.