After a review of the literature, two cases of osteoid osteoma involving phalanges of the toes are reported. Physical findings of osteoid osteoma vary with the site of the tumor; in the foot, particularly the toes, it presents various atypical and characteristic features. Its more frequent cancellous and subperiosteal localization in the small bones of hand and foot, showing atypical roentgenographic findings, poses particular problems in diagnosis. In the osteoid osteoma of the phalanges, characteristic enlargement of the toe or finger seems to be frequent and with a typical clinical history may be considered a reliable sign of suspected osteoid osteoma. Specialized imaging techniques may hasten diagnosis, but only an accurate clinical history and the characteristic findings with a high index of suspicion can allow for a proper diagnosis.