There is provided an information processing apparatus to measure a distance in a real space with a simpler operation, the information processing apparatus including: an acquisition section that acquires an image captured by a predetermined imaging section, and position information based on at least any of a position and a direction of the imaging section; an estimation section that estimates a first position and a second position in a real space, on a basis of a first image and a second image which are the image captured at each of a first viewpoint and a second viewpoint, and first position information and second position information which are the position information about each of the first viewpoint and the second viewpoint; and a measurement section that measures a distance between the first position and the second position on a basis of the estimation result.