Olde Cypress Golf Club opened in 2000 as a private residential community course in Naples, designed by P. B. Dye, son of the legendary Pete Dye. The layout reflects the Dye family's architectural philosophy while adapting to the flat Southwest Florida terrain, incorporating water features, waste bunkers, and strategic bunkering that demands thoughtful course management. The design makes extensive use of the property's natural cypress trees and wetlands, creating a more naturalistic Florida golf experience than many of the region's resort-style courses. The routing winds through a landscape dominated by native vegetation and preserves, with water coming into play on most holes. Dye's design emphasizes strategic options rather than forced carries, allowing players to choose aggressive or conservative lines based on their skill level and risk tolerance. The bunkering features the irregular, rugged edges characteristic of Dye family designs, and greens present subtle undulations that reward precise approach shots. Olde Cypress operates as a private equity club, meaning members purchase a membership rather than a real estate lot, which has shaped its club culture around golf rather than purely residential amenities. The course has developed a reputation within the Naples golf community for conditioning and playability, offering a contrast to some of the area's more resort-oriented layouts. The design holds up well for accomplished players while remaining accessible from forward tees, a balance P. B. Dye has pursued throughout his career.