Xylem structure and function are well described in woody plants, but the implications of xylem organization in less-derived plants such as ferns are poorly understood. Here, two ferns with contrasting phenology and xylem organization were selected to investigate how xylem dysfunction affects hydraulic conductivity and stomatal conductance (gs). The drought-deciduous pioneer species, Pteridium aquilinum, exhibits fronds composed of 25 to 37 highly integrated vascular bundles with many connections, high gs and moderate cavitation resistance (P50 = −2.23 MPa). By contrast, the evergreen Woodwardia fimbriata exhibits sectored fronds with 3 to 5 vascular bundles and infrequent connections, low gs and high resistance to cavitation (P50 = −5.21 MPa). Xylem-specific conductivity was significantly higher in P. aqulinium in part due to its wide, efficient conduits that supply its rapidly transpiring pinnae. These trade-offs imply that the contrasting xylem organization of these ferns mirrors their divergent life history strategies. Greater hydraulic connectivity and gs promote rapid seasonal growth, but come with the risk of increased vulnerability to cavitation in P. aquilinum, while the conservative xylem organization of W. fimbriata leads to slower growth but greater drought tolerance and frond longevity.