A growing international human population and rising living standards are increasing the demand for agricultural products. Under higher pressure over natural resources, environmental concerns are increasing as well, challenging current water use decision-making processes in irrigated agriculture. Higher agricultural productivity means water should be applied more efficiently, which requires instant information on weather, soil, and plant conditions throughout the growing season. An information-based irrigation scheduling application tightened to the spatiotemporal variability of the fields is critical for enhancing the current irrigation system and making better irrigation scheduling decisions. The aim of this study is to review current irrigation scheduling methodologies based on two case studies (woody and field crops) located in semi-arid areas of Southeast Spain. We realize that optimal irrigation programming requires consistent investment in equipment, expenditure on operation and maintenance, and qualified technical and maintenance services. These technological approaches will be worthwhile in farms with low water availability, high profitability, and significant technical-economic capacity.