Located in Historic Wailuku and built in the area of the royal residence of Kahekili, last ruling chief of Maui, Hale Hō’ike’ike made up a portion of the Wailuku Station which served as a school initially for Hawaiian girls starting in 1842. Originally the school was known as the Central Wailuku Female Seminary until funding by the American Board of Commissioners for Foreign Missions ceased in 1848. Thereafter the school was converted into a day school for both Hawaiian boys and girls on a tuition paying basis until its closure in the mid-1850ʻs. The site of the former school remained the home of Edward Bailey and his family until 1888. Later the site evolved into the Wailuku Sugar plantation and was the used as the plantation managers home until 1924 when the new plantation managers house was build next door. The house was then converted into offices for Wailuku Sugar.

Since then the old Bailey House has been the headquarters of the Civil Defense during World War II and was briefly occupied by the family of Ezra Crane, the Editor of the Maui News, whose home was destroyed by the 1946 Tsunami. The Founders of what later became the Maui Historical Society had searched for many years for a suitable location for a museum and were offered the use of the “Old Bailey House” by Wailuku Sugar in 1956. The Maui Historical Society leased the building and portion of the grounds from Wailuku Sugar for a $1.00 a year until Wailuku Sugar (by then Wailuku Agro-Business) closed and sold the entire property to Masaru "Pundy" Yokouchi in 1992. The following year Pundy Yokouchi donated the main building, annex, and 0.7 acres to the Maui Historical Society.

Edward Bailey, along with wife Caroline Bailey immigrated to Hawaii in 1837 on the ship Mary Fraizer. Before coming to Hawaii to work as a mission teacher Bailey taught at Amherst College. Upon his arrival to Hawaii, Bailey was first stationed in Kohala on Hawaiʻi Island and was later transferred to Lahaina where he taught at the Lahainaluna Seminary. Later in 1840 Bailey was sent to work at the Wailuku Female Seminary where he soon replaced Mr. Armstrong as Headmaster of the School and remained in that position until its closure in the mid 1850's. Bailey is best known for his landscape oil paintings, contributions in helping to build the fourth and current  Kaʻahumanu Church, and the commission of its clockworks. Bailey also operated a small sugarcane plantation which was later purchased by the Wailuku Sugar Plantation.