(1) Background: Degradation of soils and erosion have been described for most of the soils presented along the Maule Valley. Organic and integrated management promotes agroecosystem health, improving soil biological activity. Due to this, the aim of this research was to study the effect of organic, integrated, and conventional management on the productive, oenological and soil variables of a vineyard cultivated under semiarid conditions during 5 consecutive seasons; (2) Methods: Yield, grape and wine oenological, and soil physicochemical parameters were evaluated. Bioclimatic indices were calculated in the studied seasons; (3) Results: Conventional management allowed to improve yield and the number of bunches per vine compared to organic management. However, this latter enhanced mineral nitrogen and potassium content in soil. Based on bioclimatic indices, heat accumulation improved number of bunches per plant and most of the soil physicochemical parameters; (4) Conclusions: Organic management improved the accumulation of some microelements in soils at the expense of yield. Organic matter decreased along the study was carried out. Season was the conditioning factor of the variability of most of the studied parameters, while the interaction between season and type of management affected soluble solids, probable alcohol and pH in grapes, and total polyphenol index and pH in wines.