Orentano is the second-largest settlement in the municipality of Castelfranco di Sotto in terms of population.
Following the Black Death of 1348, Orentano, along with the villages of Staffoli and Galleno, was depopulated, and the Cerbaie hills became a bone of contention between the municipalities until the Florentine domination.
The area was only repopulated at the start of the 16th century thanks to the migration of farmers from the Valdarno. The division of its territory remained unchanged until the early 20th century, when the inhabitants decided to unite under Castelfranco di Sotto.
Orentano is home to a permanent archaeological exhibition which, through models and educational panels, illustrates life in the Padule di Bientina area from prehistoric times, through the Etruscans and Romans, up to the Middle Ages (see the canoe, approximately four metres long).
Orentano is also famous for its tradition of pastry-making. Every August, the village hosts the ‘Sagra del Bignè’ (Cream Puff Festival), which culminates in the ‘Sfilata del Dolcione’ (Parade of the Dolcione), a huge handmade cake representing a monument, a famous figure or an international icon.