Leaf-level morphological and structural adaptations to reduce water loss were examined in five olive (Olea europaea L.) tree cultivars (Arbequina, Blanqueta, Cobrançosa, Manzanilla and Negrinha) growing under field conditions with low water availability. Leaf measurements included leaf tissue thickness, stomatal density, leaf area, leaf mass per unit area, density of leaf tissue, relative water content, succulence, water saturation deficit, water content at saturation and cuticular transpiration rate. We found considerable genotypic differences among the cultivars. Negrinha, Manzanilla and Cobrançosa had more morphological and structural leaf adaptations to protect against water loss than the other cultivars. Manzanilla and Negrinha enhanced their sclerophylly by building parenchyma tissues and increasing protective structures like the upper cuticle and both the upper and lower epidermis. Cobrançosa exhibited good protection against water loss through high density of foliar tissue and by thick cuticle and trichome layers. Compared with the Negrinha, Manzanilla and Cobrançosa cultivars, Arbequina leaves had a thinner trichome layer, implying that the leaves were less protected against water loss; however, the development of smaller leaves may reduce water loss at the whole-plant level. Among cultivars, Blanqueta had the largest leaves and some anatomical traits that may lead to high water loss, especially from the adaxial surface. The mechanisms employed by the cultivars to cope with summer stress are discussed at the morpho-structural level.