Yes, with the Subscriptions & Memberships add-on for WooCommerce. A product can be billed on a repeating cycle — every X hours, days, weeks, months or years — so long-term hire becomes recurring revenue instead of a booking you have to win again every month.
The booking calendar is driven by that billing cycle, so the rental period extends as each renewal is taken and inventory is never released before the customer has paid for the next term. The same add-on also sells membership tiers and runs a rental queue, where returning one item automatically dispatches the next one the customer has lined up.
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