This study aimed to monitor the aerobic bioremediation of diesel oil-contaminated soil by measuring: a) the CO2 production; 2) the fluorescein production; 3) the residual diesel oil concentration. Moreover, the complex dielectric permittivity was monitored through an open-ended coaxial cable. Several microcosms were prepared, changing the water content (u% = 8–15% by weight), the carbon to nitrogen ratio (C/N = 20–450), and the soil amount (200 and 800 g of dry soil). The cumulative CO2 and fluorescein production showed similar trends, but different values since these two parameters reflect different features of the biological process occurring within each microcosm. The diesel oil removal efficiency depended on the microcosm characteristics. After 84 days, in the microcosms with 200 g of dry soil, the highest removal efficiency was achieved with a water content of 8% by weight and C/N = 120, while in the microcosms with 800 g of dry soil the best result was achieved with the water content equal to 12% by weight and C/N = 100. In the tested soil, the bioremediation process is efficient if the water content is in the range 8–12% by weight, and C/N is in the range 100–180; under these operative conditions, the diesel oil removal efficiency was about 65–70% after 84 days. The dielectric permittivity was monitored in microcosms with 200 g of dry soil. The open-ended coaxial cable detected significant variations of both the real and the imaginary component of the dielectric permittivity during the bioremediation process, due to the physical and chemical changes that occurred within the microcosms.