A similar complex is being developed on the opposite side of Walt Disney World called Flamingo Crossings.

[4] The 120-acre (49 ha) complex includes four distinct areas: Marketplace, The Landing, Town Center, and West Side.

Construction began the following August and Pleasure Island was opened on May 1, 1989, the same day as the Disney's Hollywood Studios theme park.

[5] In the mid-1990s, the growth of Walt Disney World created the potential for further expansion, leading to a $1 billion investment in projects across the resort.

[6] On September 15, Downtown Disney West Side, a 66 acres (27 ha) expansion, opened as a third shopping, dining, and entertainment area featuring venues such as La Nouba (the former Cirque Du Soleil show in residence which closed at the end of 2017), DisneyQuest, and Virgin Megastore.

Major changes to the complex also included the conversion of Mickey's Character Shop into the World of Disney, becoming the world's largest Disney store, in addition to the expansion and upgrade of the AMC Pleasure Island Theatres, as well as the opening of Rainforest Cafe and Planet Hollywood.

[11] In addition, a new bus terminal, with dedicated bus lanes on Buena Vista Drive, was built;[12][13] Buena Vista Drive was widened, and a new exit ramp built from Interstate 4 directly to Disney Springs, as part of the traffic upgrade.

[14] Town Center, built just south of The Landing in the surface parking lots, was opened on May 15, 2016, completing the major construction on the project.

[19] On May 24, 2024, a nighttime drone show, Dreams That Soar, began running nightly at Disney Springs, which ran until September 2, 2024.

The complex is bordered by Lake Buena Vista to the north and the parking garages and surface lots to the south.

[23] Creative director Dave Hoffman said about the area, "Each neighborhood reflects its function and [the fictional] time period when it was developed."

A walkway spanning the Village Lake and connecting Rainforest Cafe with the Lego Store—The Marketplace Causeway—was constructed and opened in 2015.

[23] The Landing features nautical-themed restaurants and shops, including Jock Lindsey's Hangar Bar—an aviation-themed dive bar based on the character from the Indiana Jones films—and The Boathouse, which serves as the port for the amphibious automobiles that offer cruises of Lake Buena Vista.

On November 18, 2010, Disney announced a project named Hyperion Wharf, which was planned to replace the Pleasure Island complex.

Pleasure Island would have undergone extensive renovations and re-theming to transform into the early twentieth century wharf-themed entertainment area.

[31] The structure originally known as the Empress Lilly is a static full-size replica of a paddle steamer riverboat on Village Lake.

[15][37] Retailers to have opened in the first phase of Town Center include Anthropologie, Uniqlo (the first of its kind in the Southeastern United States), Sephora, L'Occitane en Provence, Pandora, UGG, Johnston & Murphy, ZARA and Kate Spade and Trophy Room among many others.

[23] The expansion of the existing AMC Theatres Pleasure Island 24 venue opened with Downtown Disney West Side in 1997.

[41] The NBA Experience, which was built on the DisneyQuest site, briefly operated for 7 months from August 12, 2019, through March 2020 due to closures related to the COVID-19 pandemic.