Originally owned by Ponce de León, the lord of Chipiona,  the site was a castle fortress as can be seen with the  square-shaped tower with battlements.Don Pedro III Ponce de León, fourth lord of Marchena and first Count of Arcos donated it to the hermit monks of San Agustín (or Augustinians) in 1399, who converted to a church and thus worship the Virgin Mary and it the  Sanctuary of Our Lady of Regla. In 1835 the Augustinians were forced to leave due to the Exclusion of religious Orders. It fell into disuse for a number of years and was restored in 1851. In 1882 it was given to a Franciscan community who are still based there.

The castle has been modified multiple time since then as it adapted to its religious uses, however always retaining its fortress like image. Modifications were paid for by the Ponce de León, lords of Rota and Chipiona and the Pérez de Guzmán, lords of Sanlúcar and funds raised from visitors who offered alms to the Sanctuary.

The prestige and extended devotion that the sanctuary has is based on the venerated image of the Virgen de Regla which dates back to the first half of the year 300. The first procession took place in 1588 and was organized by the Duchess of Medina Sidonia to pray for the success of the Armada, which was led by her husband.

The building was rebuilt in an “eclectic” style at the beginning of the 20 century. The cloisters, however, have retained their 15 century architecture together with a long 17 century frieze made of azulejos (ceramic tiles) illustrating the history of the sanctuary.

The monastery widens around two courtyards: the so-called Royal and the Conventual, the latter known as the Mudéjar Courtyard and the jewel of the Sanctuary, highlighting the cistern (1460) and the mullion or mullioned window, which could be Mozarabic. The well or Humilladero was the hiding place of the carving of the Virgen of Regla during the Muslim occupation.

The statue of the Virgin Mary is one of the oldest of its kind and the legend is that St. Augustine ordered it for the Oratory at the African city of Hippo. When the Vandals overran that city, some Augustinian hermits brought it to Chipiona in the 5th century.