By law, brothel patrons were only allowed to stay for a night and a day at a time. Social classes were not strictly divided in Yoshiwara a commoner with enough money would be served as an equal to a samurai, and though samurai were discouraged from entering Yoshiwara, they often did so, the only requirement being that their weapons be left at the town's entrance. Another path to success and eventual freedom for a working woman in Yoshiwara was for a rich man to buy out her contract from the brothel, and thus keep her as his wife or mistress a further path would be for a woman to work successfully enough that she could eventually buy her own freedom, though this was an uncommon and infrequent occurrence. If chosen to receive the correct training at a young age, a girl indentured to a brothel could become an apprentice to a high-ranking courtesan when the girl was old enough and had completed her training, she would become a courtesan herself and work her way up the ranks. Despite this, many women also died of sexually transmitted diseases, or following failed abortions, before completing their contracts. In these cases, the advanced payments a woman's parents received could be used to fund her dowry.

However, a significant number either served out their contracts and married a client, went into other employment (including other forms of prostitution), or returned to their family homes. Though contracts of indenture often did not last more than five to ten years, the debt sometimes accrued by these women could keep them working there for much longer. Many were typically indentured to their brothel if indentured by their parents, a larger advance payment would often be received.

Yoshiwara was home to some 1,750 women in the 18th century, with records of some 3,000 women from all over Japan at one time.

Having been established some decades earlier, the original Yoshiwara district burned down, along with much of the city, in the Great fire of Meireki of 1657 it was then rebuilt in its new location, named 'Shin Yoshiwara' ('New Yoshiwara'), the old location being known as 'Moto Yoshiwara' ('Original Yoshiwara'), though the moniker of 'new' was eventually dropped, with the rebuilt district becoming known simply as Yoshiwara. In 1656, due to the need for space as the city grew, the government decided to relocate Yoshiwara, with plans being made to move the district to its present location north of Asakusa on the outskirts of the city. The licensed district of Yoshiwara was created in the city of Edo, near to the area today known as Nihonbashi, itself close to the beginning of the Tōkaidō road, the primary route to western Kyoto during the Edo period. Yoshiwara during the Taisho era in the 1920's

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