A vehicle insurance system includes: a registration unit that registers a subject vehicle including a power storage device and a subject period in response to payment of an insurance premium for the subject period when the subject vehicle is sold; a ranking unit that ranks a purchaser of the subject vehicle based on vehicle usage information about vehicle usage of the purchaser; an insurance premium determination unit that determines at least one of the insurance premium for the subject period and a renewal fee for extending the subject period, based on a rank of the purchaser; and an insurance benefit determination unit that determines an insurance benefit compensating for at least a part of a loss of asset value of the power storage device due to degradation of the power storage device, when the subject vehicle is sold within the subject period.