Guadalcanal

In 1241 the town was captured from Arab control by Rodrigo Íñiguez, fifteenth master of the Order of Santiago, and came under the Order's jurisdiction, attached to its province of León. During the late medieval period it was caught up in the power struggle between Enrique de Guzmán, Duke of Medina Sidonia, and Alfonso de Cárdenas for the mastership of the Order. On Carnival day in 1475, Cárdenas surprised his rivals here, and his followers seized a large haul including the Duke's personal belongings; the Duke barely escaped with his life under cover of darkness.

The town had long been fortified, but its defences were ordered demolished as punishment for its role in the Revolt of the Comuneros. Arab fortress remains have been identified near the church of Santa María de la Asunción, and sections of town wall can still be traced.

By the 1528 census, Guadalcanal had 1,057 households and was the most populous town in the district, described as "rich in trade and wealth." A century later it still counted over 1,000 households across three parishes. The 1753 Ensenada cadastre records it within the Order of Santiago's Llerena district, with land under irrigation, pasture, vineyard, olive grove, and holm oak, and two hospitals, four convents, and a Basilian hospice.

It was not until 1833 that the town left its centuries-long administrative ties to Extremadura and became part of the province of Sevilla in Andalucía. During the Peninsular War, troops passed through repeatedly; in January 1810, the Duke of Alburquerque's forces marched through on their way to defend Sevilla, and the town was occupied by Gabriel de Mendizábal's forces until early 1811. Population peaked around 7,000 in the mid-twentieth century; today roughly 2,500 people live here.

The main parish church stands on the central Plaza de España alongside the town hall and the former church of San Vicente. It is a Gothic-Mudéjar building with a Latin cross plan, three stepped naves, and a bell tower at the front. The doorway to the sacristy preserves a piece of the Arab alcazaba that once occupied the site. The rear apse area includes a clock tower in a Neo-Mudéjar style, added in the 1930s.

The church of Santa Ana sits on a rise above the town with views over much of it. Built in Mudéjar style between the late fifteenth and early sixteenth centuries and later extended, it has a single nave with transverse arches, a three-arched pointed portico framed with alfices on octagonal pillars, and a three-stage facade tower. Its chapels and retablos from the sixteenth and seventeenth centuries are notable. Declared a national historic-artistic monument in 1979, it is now a cultural heritage site used as an interpretation centre after urgent restoration works in 1997–99.

The oldest civil monument in the region dates from 1307 and was built as the supply house of the Master of the Order of Santiago. An external ramp once allowed horse access to the upper floor. It is privately owned, partially restored, and open to the public as a restaurant.

Other medieval churches survive in various states: San Sebastián, de-consecrated and used as a covered market in the twentieth century, is Gothic-Mudéjar with notably tall pilasters and pointed transverse arches. The Convento del Espíritu Santo formerly served as a school and is in better condition than most. The old Hospital de los Milagros is in advanced ruin. Outlying hermitages include those of San Benito and Nuestra Señora de Guaditoca, patron of the town.