Kiwifruit decline syndrome (KiDS) has affected kiwifruit orchards for more than ten years in the Mediterranean area, severely compromising productivity and causing extensive uprooting. The affected plants go through an irreversible and fast wilting process. The problem has not been solved yet, and a single cause has not been identified. In this work, we carried out a survey on ten five-year-old healthy kiwifruit cv. Hayward plants cultivated in an area strongly affected by KiDS are characterised by a rising temperature and vapor pressure deficit (VPD). Five plants were located in a KiDS-affected orchard. Our goal was to assess the hydraulic conductance of asymptomatic plants in a KiDS-affected area where rising climate change stress is underway. Our hypothesis was that a rising temperature and VPD could impair xylem functionality, leading the plants to develop strategies of tolerance, such as vessel narrowing, or stress symptoms, such as cavitation or implosion, inducing a higher risk of KiDS onset. Hydraulic conductance was investigated using a physiological and morphological approach to detect trunk sap flow; trunk growth and daily diameter variations; leaf gas exchanges and temperature; stem water potential; and the root xylem vessel diameter and vulnerability to cavitation. A strong xylem vessel narrowing was observed in all plants, with the highest frequency in the 30–45 µm diameter class, which is an indicator of long-term adaptation to a rising VPD. In some plants, cavitation and implosion were also observed, which are indicative of a short-term stress response; this behaviour was detected in the plants in the KiDS-affected orchard, where a high leaf temperature (>39 °C), low stomatal conductance (<0.20 mol H2O m−2 s−1) and transpiration (<3 mmol H2O m−2 s−1), low stem water potential (<−1 MPa), high vulnerability to cavitation (3.7 μm mm−2), low trunk sap flow and high daily stem diameter variation confirmed the water stress status. The concurrence of climate stress and agronomic management in predisposing conditions favourable to KiDS onset are discussed, evidencing the role of soil preparation, propagation material and previous crop.