Vascular tumors of bone can be diagnostically challenging because of their rarity and histologic overlap with diverse mimics. Vascular tumors of bone can be categorized as benign (hemangioma), intermediate-locally aggressive (epithelioid hemangioma), intermediate-rarely metastasizing (pseudomyogenic hemangioendothelioma), and malignant (epithelioid hemangioendothelioma and angiosarcoma). Recurrent genetic alterations have been described, such as FOSB rearrangements in pseudomyogenic hemangioendothelioma and a subset of epithelioid hemangiomas; CAMTA1 or TFE3 rearrangements in epithelioid hemangioendothelioma. This review discusses the clinical, histologic, and molecular features of vascular tumors of bone, along with diagnostic pitfalls and strategies for avoidance.