Introduction: Intraosseous lipomas are benign tumors composed of mature fat that reside within the intramedullary canal. Although many cases are asymptomatic, some patients report pain that interferes with daily living. For patients presenting with refractory pain, surgical excision may be performed. These tumors were once thought to be rare, but a recent increase in awareness and diagnostic capability may contradict this. Case Presentations: A 27-year-old female presented with a 3-month history of deep and aching pain in her left shoulder. The second patient was a 24-year-old female who presented with a 3-year history of pain in her right tibia. The third was a 50 year old female who presented with a 4-month history of deep pain in her right humerus. The fourth patient was a 34-year-old female who presented with a 6-month history of the left heel pain. All were found to have intraosseous lipomas and were treated with excisional curettage, achieving resolution of symptoms. Conclusion: These cases may help orthopedists better understand the presentation and treatment of intraosseous lipomas due to several shared characteristics. We also hope that this report may lead clinicians to include this pathology in their differential diagnosis when patients present with similar symptoms. As the prevalence of these tumors appears to be increasing, efficient diagnosis and treatment will become increasingly valuable to orthopedists and patients.