Angiomatoid Spitz nevus is a recently described subtype of desmoplastic Spitz nevus. Six cases have been described in the literature thus far. Here, we describe six additional cases of angiomatoid Spitz nevus and provide a review of the literature on this entity. The features of classic angiomatoid Spitz nevus are described in the context of important differential diagnostic considerations, particularly regressed malignant melanoma.