Conservation agriculture (i.e., minimized soil disturbance and permanent soil covering) and living mulches represent two agroecological practices that can improve soil fertility, spontaneous flora, and beneficial insect communities. This research studied the effect of these practices in a young olive orchard in the Mediterranean area. Two Sicilian olive cultivars (‘Nocellara del Belice’ and ‘Nocellara etnea’) were used for the field experiment; inter-row minimum and zero tillage and four species of aromatic plants as living mulch along the row were tested. Spontaneous flora and beneficial insect communities, as well as tree growth, were monitored. The inter-row management did not influence the spontaneous flora dynamics. The species adopted for living mulch showed a very different degree of development and soil cover; 69 insect species (pollinators and predators) belonging to five orders (Hymenoptera, Lepidoptera, Diptera, Neuroptera, and Coleoptera) and 17 families were recorded. The growth of the olive trees was not affected by the conservative strategies.: In the inter-row, the growth of the spontaneous flora was limited by the high temperatures during the summer. Among the living mulch species, sage and lemongrass guaranteed an almost full soil cover, reducing the need for weed management along the row, as well as increasing the beneficial insects without influencing the young tree growth.