Coccidioidomycosis, also known as San Joaquin Valley Fever or Valley Fever, is mostly a pulmonary infection caused by inhalation of spores in an endemic region. Dissemination to bone, joints, meninges, and skin occurs less than one percent of the time. Skeletal involvement accounts for approximately half of the disseminated coccidioidomycosis with the vertebrae as the most common skeletal region. We present a very rare case of disseminated coccidioidomycosis with osteomyelitis and compression fracture of the lumbar vertebral body. This case depicts some of the potential issues that can arise in managing coccidioidomycosis, especially when noncompliance to initial azoles occurs, that can lead to dissemination and complicated bone infections necessitating surgical intervention along with continuous medical therapy.