An information processing system according to the present disclosure includes an owner terminal, a user terminal, and a management device. The owner terminal outputs vehicle information indicating whether at least a partial period of a lendable period is designated as a standing period in which a vehicle is not traveling. The user terminal outputs driver’s license information indicating whether a user is holding a driver’s license. The managing apparatus selects a vehicle at least a vehicle cabin of which is available to the user from a plurality of vehicles including a vehicle in a standing period in a lendable period, based on matching permission information, in which correspondences among whether vehicles are in respective standing periods, whether users are holding respective driver’s licenses, and whether vehicle lending is permitted are registered in advance, the vehicle information, and the driver’s license information, and outputs information indicating the selected vehicle.