A vehicle monitoring system includes at least one camera, and a server that is communicably connected to a client terminal. The camera performs capturing a vehicle while switching a first capturing condition including an image parameter for capturing a number of the vehicle entering an angle of view of the camera and a second capturing condition including an image parameter for capturing an occupant's face of the vehicle, and transmits a first captured video under the first capturing condition and a second captured video under the second capturing condition to the server. The server arranges reproduction screens for the first captured video and the second captured video that are reproduceable in the client terminal and displays the reproduction screens on the client terminal based on the first captured video and the second captured video.