Eleven Italian monovarietal extra virgin olive oils (MEVOOs) (Carboncella, Coratina, Frantoio, Leccino, Marzio, Maurino, Moraiolo, Piantone di Falerone, Pendolino, Rosciola, Sargano di Fermo) from olives grown in the same experimental olive orchard, under the same conditions (fertilization, irrigation), and processed with the same technology (three-way continuous plant) were investigated. As a result, the impact of the olive cultivar on fatty acid and triacylglycerols composition, oxidative stability, polar phenolic profile and sensory properties (panel test) of the oil was assessed. Pendolino, Maurino and Marzio oils presented the highest levels (p < 0.01) of palmitic, linoleic and linolenic acids % and the lowest oleic:linoleic ratio. Within triacylglycerols, triolein (OOO) strongly varied among the oils, with Coratina and Leccino having the highest content. Frantoio showed the lowest 1-Stearoyl-2-palmitoyl-3-oleylglycerol and 1,3-Distearoyl-2-oleylglycerol amounts. Rosciola showed the highest level (p < 0.01) for two of the most abundant secoiridoid derivatives (the dialdehydic forms of decarboxymethyl elenolic acid linked to hydroxytyrosol and tyrosol). A good correlation was found between total phenolic content and oxidative stability, indicating Marzio and Leccino respectively as the richest and poorest genotypes. Sensory variability among varieties was mainly linked to perceived bitterness, pungency and fruitiness, while no effects were found on secondary flavors.