As the name originates from a fictional location in Walt Disney's 1940 film Pinocchio, Pleasure Island opened emulating Church Street Station in Downtown Orlando, Florida.

Merriweather Pleasure was said to be an industrialist and explorer who decided to move his family to Florida and start a new sailmaking and yacht construction business on the island during the 1920s through early 1940s.

He enjoyed throwing parties for his employees and friends after hours, but, eventually, he was lost at sea, his sons failed at running the company without him, and the island was mostly destroyed in a storm.

Since there was no longer an entry fee, the free entertainment provided by these stages was attracting large groups of local teens, which was considered undesirable.

The removal of the Hub Stage opened a small area to a view of the lagoon located behind Pleasure Island, including a dock.

The construction of new docks allow boat transportation links between West Side, Pleasure Island, Marketplace, and Disney resorts across the lagoon and up the Sassagoula River.

In late June 2008, Disney announced that the six remaining night clubs at Pleasure Island would close by September 28, 2008, to make room for additional family-oriented entertainment.

[citation needed] Disney officials stated that the Pleasure Island nightclub closures are in response to customers who desire more broad-based dining and retail opportunities.

Among the capacity crowd were many of its past actors and cast members, some of whom started to line up at 9:00 in the morning to ensure entrance to what would be a very emotional and busy night.

In February 2009, amid rumors of a partial reopening of Pleasure Island, Disney announced that three former clubs would become available for private party rentals.

Instead, the area focuses on retail and restaurants, though one restaurant circuitously links the new area to its predecessor: Jock Lindsey's Hangar Bar was ostensibly opened by pilot Jock Lindsey (who appeared in the 1981 Indiana Jones film Raiders of the Lost Ark), who is a member of the Society of Explorers and Adventurers.