The intensification of bovine milk production in the Azores has led farmers to increase farm size and specialization in grasslands, implementing confined and semi-confined production systems. Fixed milking parlours (FMP) have progressively gained more popularity, at the expense of conventional mobile milking systems (MMS). The present study aimed to evaluate the associations between production and health management in dairy cattle farms, with FMP or MMS, in grasslands (São Miguel, Azores), according to the farmers’ perspective. A total of 102 questions about production and health management were surveyed in 105 farms with >30 dairy cows each. Farms with FMP were associated (p ≤ 0.05) with larger herd size, better facilities, and specialized management, however, the adoption of preventive and biosecurity measures should be improved by these farmers. MMS farms implemented a lower level of disease prevention or control programs, less frequent transhumance, and showed a wider vocation to dual-purpose (milk and cross beef) than FMP farms. In conclusion, MMS and FMP farms tried to optimize yield and economic viability in different ways using grasslands. Several biosecurity and health prevention constraints were identified for improvement.