Studies on insect pollinator ecology and dynamics are rarely conducted in traditional Indian agricultural landscapes. Indiscriminate landscape modifications in rural areas and the increasing tendency toward crop monocultures may significantly affect pollinator habitats and effectiveness. This study aimed to observe insect pollinators, their visitation frequencies, and visitation timing on monsoon cucurbit crops such as Cucumis sativus L., C. pubescens Willd., Momordica charantia L., Trichosanthes anguina L., and Luffa acutangula (Roxb.) in a coastal village in Karnataka. The study also examined the significance of surrounding landscape elements in sustaining pollinator populations. Bees such as Apis dorsata, A. cerana, and Trigona sp. were the major visitors of all cucurbit crops, except snake gourd, which was primarily pollinated by lepidopterans. Insect species were found to partition floral resources with minimal overlap in their visitation times. Natural landscape elements—particularly the village forest and rocky savanna—provided important habitats for bees and lepidopterans. Prolifically blooming monsoon herbs on lateritic plateaus appeared to play a key role in supporting pollinator populations by providing nectar resources. These factors may contribute to the case study village being well known for its monsoon vegetables.