Table olives represent one of the most important fermented products in Greece. Their highly appreciated flavor is directly associated with the volatile composition. However, extensive data on the volatile profile of table olives from Greek cultivars are scarce in the literature. For this reason, the volatile components of industrially fermented table olives from Kalamata, Conservolea and Halkidiki cultivars grown in different geographical areas within Greece were determined using headspace solid-phase microextraction combined with gas chromatography–mass spectrometry. More than 100 volatile compounds were identified and distributed over different chemical classes. All samples were rich in esters, alcohols and acids, whereas the samples of cv. Halkidiki were also characterized by increased levels of volatile phenols. Both qualitative and quantitative differences were observed, which resulted in the discrimination of the table olives according to olive cultivar and growing location. To the best of our knowledge, this is the first systematic study on the volatile profiles of table olives from Greek cultivars that also highlights the pronounced effect of olives’ growing location.