Background and Aims The deceptive strategies by which orchids are pollinated and how these are capable of attracting pollinators remain understudied with regard to their implications for plant fitness. Despite their ecological importance, limited investigations have been conducted on sexual deception and shelter mimicry in orchid species, making this a compelling avenue in orchid biology research. To expand the knowledge of these reproductive mechanisms, we studied the pollination of Serapias lingua and S. parviflora in co-occurring and isolated sites in the Balearic Islands (Spain), further accentuated by the presence of a hybrid, indicating shared pollinators.Methods We employed bagging and hand pollination experiments to examine the reproductive biology of the two species. Furthermore, we evaluated the influence of phenotypical and ecological factors on reproductive success, including biometric measurements, reproductive performance and neighbourhood diversity (co-flowering and pollinator communities).Key Results Reproductive mechanisms between these two orchid species exhibit substantial disparities. Serapias lingua relies primarily on insect-mediated pollination, while S. parviflora demonstrates self-reproduction capacity. Although events of open pollination are rare, hybridization occurs predominantly when S. lingua is the pollen donor. Fruit set in S. parviflora was positively correlated with plant height, while in S. lingua it was negatively associated with flower size. The coexistence of the two species positively affected pollinium removal in S. parviflora, but did not exert an influence on reproductive traits in S. lingua. Overall, biometric parameters were diminished in isolated compared with co-occurring sites. At the community level, the increased diversity of co-flowering species in the vicinity exhibited an inhibitory effect on pollinium removal in S. parviflora.Conclusions Under a context of pollinator loss or phenological mismatch between pollinator presence and flowering, the selfing capacity of S. parviflora would guarantee reproduction whereas S. lingua survival would be compromised. Furthers studies are needed to assess the effects of phenotypical and ecological factors on reproductive success of S. lingua in pollinator-decline scenarios.