Plaza de Santa Ana gets its name from the convent that stood here until the nineteenth century. This large, open space is now a popular meeting place with lots of cafes and tapas bars. The square is dominated by the Teatro Espanol, which has developed over the centuries form a courtyard playhouse into a grand edifice.

The open, wooden playhouse was replaced in 1745 by a covered Italian style theatre, which was rebuilt by Juan de Villanueva following a fire at the beginning of the nineteenth century. After the square was created by the demolition of the convent, owners added a new neoclassic facade, featuring medallions with busts of famous playwrights. The interior was rebuilt after another fire in 1975, and the theatre now stages classical and contemporary plays.

The bullfighters favoured the Hotel Reina Victoria with its gleaming cream façade and distinctive corner beacon at the top of the square. Built in 1919, it closed in 2005 and was converted into the first Hard Rock hotel in Europe.