Food product transportation is one of the most problematic tasks considering the specific expectations in the context of the transport conditions. It seems to be a significant challenge for the freight carriers’ decision-makers. The proper organization and management of that process is the basis for the appropriate fulfilment of the needs of customers, related, among others, to the proper quality of delivered products (such as freshness, expiration date, etc.). The additional challenge in this context is the efficient delivery at the city area, taking into account typical city transportation problems, such as congestion, narrow ways, lack of the unloading areas, etc. The role of these tasks is analyzed in this paper, on the basis of the chosen parameters and technologies of the transportation process. The purpose of this paper is to study the rational freight fleet formation in the case of changing the parameters of material flow in time. It was found that with the other unchanged parameters of material flow, the change in ambient temperature affects the technological process of transportation, the type of vehicle for its movement and the structure of the vehicle fleet. Accordingly, the types of vehicles (tent or insulated) necessary for the movement of certain material flows, which require special conditions for their transportation, have been determined, in compliance with the temperature regime and periods of their use. The organization scenarios of the transport service of the studied distribution processes were proposed, taking into consideration the change in conditions for the transportation of material flow, purchase of insulated semitrailers or their rent. The proposed versions were calculated and evaluated under the given conditions, and based on the net present value, the best of the proposed options was found: the purchase of one insulated semi-trailer while hiring the remaining insufficient insulated vehicles.