The soil erosion rates are high in the rainfed olive (Olea europaea L.) mountain plantations applying conventional practices in a semi-arid Mediterranean environment, which compromise their long-term sustainability. The implementation of sustainable soil management strategies is vital for hillslopes and low-fertility soils where plantations cover vast tracts of land. In Lanjarón (Granada, Spain), the soil erosion and runoff patterns over a 4-year monitoring period were studied in erosion plots on a mountainside under four types of production systems: (1) organic (spontaneous vegetation and leguminous covers), (2) conservation agriculture (combinations of minimum tillage with spontaneous and leguminous strips), (3) integrated (combinations of no-tillage with spontaneous vegetation and leguminous strips), and (4) conventional tillage. The olive yield responses to each production system were evaluated, and the selected physico-chemical soil properties (pH, bulk density, soil organic carbon, cation exchange capacity, and total N, P, and K), soil enzymes (β-glucosidase, protease, dehydrogenase, and phosphatase activities), and soil-microbial biomass C and N were monitored. Throughout the study period, the erosion rates for organic, conservation, integrated, and conventional systems averaged 0.70, 2.10, 1.52, and 3.25 t ha −1 year −1 with runoff of 5.8, 6.3, 11.9, and 17.6 mm year −1 , respectively. The mean olive yield was not significantly affected by the production system applied, being 2.43, 2.10, 2.04, and 2.11 t ha −1 year −1 for integrated, organic, conservation, and conventional, respectively. Here, we show a substantial improvement in soil health restoration using the organic rather than a conventional system. Our findings suggest that sustainable cropping systems on hillslopes integrating a blend between organic and conventional doctrines better maintain or improve soil ecosystem functioning. This study highlights a balanced design for an integrated production system for rainfed olive orchards that can maintain productivity while suitably encouraging environmental quality and ecosystem services.