The earliest inhabitants of Jumby Bay Island were South American Indians, beginning with the Siboney who arrived here about 1775 BC. Most came to the island to mine flint, which was exported to other islands. Around 50 AD, the Arawaks arrived to Jumby Bay but were in turn displaced by the Caribs, an Indian tribe that continued to raid the island until 1674, at which time English settlers had replaced the Spaniards who colonized the island in the 1500s.
The first European to discover the island was Christopher Columbus, an Italian sailing under Spanish colors in 1493. King Charles I granted Jumby Bay Island to Earl of Carlisle, the first recorded owner in 1627. In 1835 a Mr. Jarvis (owner of Jumby Bay at that time) rented the island to emancipated slaves who grew provisions to sell on Antigua. In 1935 an heir to the property used Jumby Bay to raise sheep. These sheep were descendants from those brought to the island by Spanish settlers who lived on the island in the 16th Century. The wild sheep seen roaming on Jumby Bay today are descendants of those sheep.
Jumby Bay was uninhabited for more than four decades before work began in the 1980s. In 1983 Jumby Bay opened as a private resort. Rosewood Hotels & Resorts assumed management of the resort in April 2002.