Holladay Park Plaza's rich history began in the early 1960s, when the Presbytery of the Cascades signed a 99-year lease with the Lloyd Corporation to build a continuing care retirement community close to downtown Portland. The community, called Holladay Park Plaza, would be geared toward residents looking for a lively, metropolitan lifestyle. Construction began in 1963, and the first occupants moved to the Plaza in 1967.

In 1999, Holladay Park Plaza, a not-for-profit corporation, became part of the Pacific Retirement Services' family of affiliates. Pacific Retirement Services, Inc. (PRS), along with a local Board of Directors, establishes policies to maintain Holladay Park Plaza's essential mission. The PRS family of affiliates includes Cascade Manor in Eugene, OR; Mirabella at South Waterfront in Portland, OR; Rogue Valley Manor in Medford, OR; Trinity Terrace in Fort Worth, TX; Mirabella at South Lake Union in Seattle, WA; and University Retirement Community in Davis, CA. In addition, PRS manages two additional retirement communities in California—Saratoga Retirement Community, and the Meadows of Napa Valley—and provides affordable senior housing with twenty-three affordable housing communities for low-income seniors throughout Oregon, California, and Texas.