As agriculture has an increasing impact on the environment, new techniques can help meet future food needs while maintaining or reducing the environmental footprint. Those techniques must incorporate a range of sensing, communication, and data analysis technologies to make informed management decisions, such as those related to the use of water, fertilizer, pesticides, seeds, fuel, labor, etc., to help increase crop production and reduce water and nutrient losses, as well as negative environmental impacts. In this study, a Bidirectional Long Short-Term Memory (BiLSTM) model was trained on real data from Internet of Things sensors in a vineyard located in the Douro wine-growing region, from 2018–2021, to evaluate the ability of this model to predict the Fraction of Transpirable Soil Water (FTSW). The model uses historical data, including reference evapotranspiration, relative humidity, vapor pressure deficit, and rainfall, and outputs the FTSW for periods of one, three, five, and seven days. The model achieved an RMSE between 8.3% and 16.6% and an R2-score between 0.75 and 0.93. The model was validated on an independent dataset collected in 2002–2004 from a different vineyard located in the Lisbon wine-growing region, Portugal, and achieved an R2-score of 87% and an RMSE of 10.36%. Finally, the performance of the FTSW in the vineyard prediction model was compared with that of the Random Forest model, support vector regression, and linear regression. The results showed that BiLSTM performed better than the RF model on the unseen data, and the BiLSTM model can be considered a suitable model for the accurate prediction of the FTSW.