A method and system are disclosed and include obtaining, using a processor configured to execute instructions stored in a nontransitory computer-readable medium and in response to receiving a vehicle-sharing request, contextual information, which includes at least one of (i) vehicle selection history information associated with a vehicle-sharing account corresponding to the vehicle-sharing request, (ii) location information associated with the vehicle-sharing request, and (iii) application information associated with a portable device corresponding to the vehicle-sharing request. The method also includes generating, using the processor, vehicle recommendations based on the contextual information. The method also includes transmitting, using the processor, a first set of vehicle recommendations to the portable device. The method also includes assigning, using the processor and in response to receiving a signal indicating a selection of a vehicle from the first set of vehicle recommendations, the vehicle to a user associated with the vehicle-sharing request.