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The cliff rose (<i>Armeria maritima</i>), like other halophytes, has a phenolics-based antioxidant system that allows it to grow in saline habitats. Provided that antioxidant properties are usually accompanied by antimicrobial activity, in this study we investigated the phytochemicals present in a hydromethanolic extract of <i>A. maritima</i> flowers and explored its antifungal potential. The main phytocompounds, identified by gas chromatography–mass spectrometry, were: hexadecanoic acid, octadecanoic acid, 9-octadecenoic acid, 3-(3,4-dihydroxy-phenyl)-acrylic acid ethyl ester, and benzeneacetaldehyde. The antifungal activity of the extract and its main constituents—alone and in combination with chitosan oligomers—was tested against six pathogenic taxa associated with soil-borne diseases of plant hosts in the family Cucurbitaceae: <i>Fusarium equiseti</i>, <i>F. oxysporum</i> f. sp. <i>niveum</i>, <i>Macrophomina phaseolina</i>, <i>Neocosmospora falciformis</i>, <i>N. keratoplastica</i>, and <i>Sclerotinia sclerotiorum</i>. In in vitro tests, EC₉₀ effective concentrations in the 166−865 μg·mL⁻¹ range were obtained for the chitosan oligomers–<i>A. maritima</i> extract conjugate complexes, lower than those obtained for fosetyl-Al and azoxystrobin synthetic fungicides tested for comparison purposes, and even outperforming mancozeb against <i>F. equiseti</i>. In ex situ tests against <i>S. sclerotiorum</i> conducted on artificially inoculated cucumber slices, full protection was achieved at a dose of 250 μg·mL⁻¹. Thus, the reported results support the valorization of <i>A. maritima</i> as a source of biorationals for Cucurbitaceae pathogens protection, suitable for both organic and conventional agriculture.