Coriandrum sativum L. and Foeniculum vulgare Mill. are two aromatic and medicinal Apiaceae species commonly grown in Portugal, whose essential oils (EOs) are used in the food, pharmaceutical, and cosmetics industries. The present study evaluated EOs isolated from the fruits and vegetative aerial parts (VAPs) of 11 samples of Coriandrum sativum L. and from the fruits of 19 samples of Foeniculum vulgare Mill. The plant material was grown in experimental fields, after collection from several regions of mainland Portugal. The EOs were isolated by hydrodistillation and analyzed by gas chromatography and gas chromatography–mass spectrometry. The coriander EOs analysis evidenced two main clusters, with the first containing the fruits’ EOs dominated by linalool (60–73%), γ-terpinene, and α-pinene and the second with the VAPs’ EOs, which showed 2-trans-decenal (37–63%) and n-decanal (13–30%) as the main compounds. The fennel EOs analysis revealed two well correlated clusters, the first dominated by estragole (34–76%) and fenchone (16–30%) and the other dominated by trans-anethole (37–56%) and fenchone (14–34%). The present data suggest coriander EOs’ chemical descriptors as linalool for the fruits’ EOs and 2-trans-decenal with n-decanal for the VAPs’ EOs. For the fennel fruit EOs, the putative descriptors were trans-anethole and estragole, with variable fenchone content. The gathered data reinforce the relevance of clarifying variability of these species’ EOs, particularly when considering aromatic and medicinal plants with such a wide range of applications.