This work presents a monitoring system for the environmental conditions of rose flower-cultivation in greenhouses. Its main objective is to improve the quality of the crops while regulating the production time. To this end, a system consisting of autonomous quadruped vehicles connected with a wireless sensor network (WSN) is developed, which supports the decision-making on type of action to be carried out in a greenhouse to maintain the appropriate environmental conditions for rose cultivation. A data analysis process was carried out, aimed at designing an in-situ intelligent system able to make proper decisions regarding the cultivation process. This process involves stages for balancing data, prototype selection, and supervised classification. The proposed system produces a significant reduction of data in the training set obtained by the WSN while reaching a high classification performance in real conditions—amounting to 90% and 97.5%, respectively. As a remarkable outcome, it is also provided an approach to ensure correct planning and selection of routes for the autonomous vehicle through the global positioning system.