Some physiological, oxidative, and antioxidant enzymatic patterns were assessed in plants of three local Sicilian landraces of long shelf-life tomatoes (‘Custonaci’, ‘Salina’, and ‘Vulcano’), as compared to the commercial tomato hybrid ‘Faino’ (control). Three water treatments were considered in open-field: DRY (no irrigation); IRR (long-season full irrigation); REW (drought/rewatering cycles). During the growing season, soil water deficit (SWD) was estimated, and relative water content (RWC), specific leaf area (SLA), proline and malondialdehyde (MDA) content, and glutathione peroxidase (GPX), catalase (CAT), and superoxide dismutase (SOD) activities were measured in leaves. Differently from control, RWC in local landraces exhibited a similar pattern in REW and DRY, indicating a low capacity to re-hydrate after rewatering. Positive correlation of proline content vs. SWD in all local landraces highlights an osmotic adjustment occurring in these tomatoes in response to limited soil water content. Long shelf-life tomatoes suffered minor oxidative stress due to severe soil water deficit, as revealed by the lower levels of MDA with respect to the control. Significant correlation of CAT vs. SWD for all tomatoes indicates that this antioxidant enzyme, among those analyzed, may be considered as a biomarker for a water stress condition more than for oxidative stress due to water deficit.