The present technology relates to an information processing device, an information processing method, and a program capable of facilitating fixed-point observation on skin condition. The information processing device according to an aspect of the present technology acquires an image that shows a predetermined feature point of a user who is a measurer of skin condition, and a measurement portion of skin condition, and analyzes the image, and then recognizes a position of the feature point. Furthermore, information indicating the measurement portion is displayed at a predetermined position on the image while setting, as a reference, the recognized position of the feature point. The present technology is applicable to information processing devices such as a tablet terminal, a smartphone, and a personal computer.