To provide a positioning system, a positioning method, and a positioning server, which are capable of improving accuracy in detection of a position. In a positioning system, three or more access points connected to a terminal station by wireless communication are connected to a positioning server through a network, the access points transmit, to the positioning server, information regarding times of having received a signal transmitted from any one of the access points or the terminal station, and the positioning server measures a position of the terminal station based on the information regarding the times, the information having been received from the access points. In the positioning system, the access points select a communication method for maximizing a strength of the signal received from the terminal station and receive the signal from the terminal station, and the positioning server measures the position of the terminal station based on the information regarding the times, the information having been received from the access points.