Castiglion Fiorentino

Travel Guide

Photo by Sophia Field
Photo by Sophia Field
Photo by Daniel Reed
Photo by Daniel Reed
Photo by Giammy McMario
Photo by Giammy McMario
Photo "Castiglion Fiorentino" by Pigellino (CC BY) / Cropped from original
Photo by Pigellino (CC BY)
Photo "Castiglion Fiorentino" by Pigellino (CC BY) / Cropped from original
Photo by Pigellino (CC BY)
Farmhouse in the hills with panoramic view and swimming pool

Farmhouse in the hills with panoramic view and swimming pool

Ristonchia
Book a stay at this family-friendly vacation home in Castiglion Fiorentino. Enjoy private pools, a garden, and laundry facilities. Popular attractions Tennis ...
9.4/10 Exceptional! (66 reviews)
Family vacation
"Was wonderful and beautiful."

Reviewed on 30 November 2024

Get rates
Farmhouse in the hills with panoramic view and swimming pool
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10, Montepulciano, SI
The price is SAR 1,849 per night from Aug 25 to Aug 26
SAR 1,849
SAR 2,061 total
25 Aug - 26 Aug
includes taxes & fees
Stay at this 5-star luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (103 reviews)
"The staff were incredibly kind and helpful. I got a flat tire the day I was leaving the hotel and the staff went above and beyond to help me get the tire fixed so I could be on my way. The hotel is beautiful and the food was excellent. I also requested a more private room and the staff changed the ..."

Reviewed on 19 July 2025

Precise Tale Poggio Alla Sala
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6, Cortona, AR
The price is SAR 2,204 per night from Aug 16 to Aug 17
SAR 2,204
SAR 2,460 total
16 Aug - 17 Aug
includes taxes & fees
Stay at this 5-star luxury hotel in Cortona. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9.6/10 Exceptional! (215 reviews)
"Would definitely come back! The Italian garden at the property is beautiful."

Reviewed on 9 July 2025

Villa di Piazzano - Small Luxury Hotel of the World
See all 6,816 properties in Castiglion Fiorentino
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Farmhouse in the hills with panoramic view and swimming pool

Farmhouse in the hills with panoramic view and swimming pool

Ristonchia
Book a stay at this family-friendly vacation home in Castiglion Fiorentino. Enjoy private pools, a garden, and laundry facilities. Popular attractions Tennis ...
9.4/10 Exceptional! (66 reviews)
Family vacation
"Was wonderful and beautiful."

Reviewed on 30 November 2024

Farmhouse in the hills with panoramic view and swimming pool
Secluded position,villa with private pool,ideal for families, close to Cortona.

Secluded position,villa with private pool,ideal for families, close to Cortona.

Toscana
Book a stay at this family-friendly villa in Castiglion Fiorentino. Enjoy free WiFi, private pools, and a garden. Popular attractions Parrocchia S. Biago and ...
9.8/10 Exceptional! (44 reviews)
Best Family Birthday Ever
"We celebrated my wife’s special birthday at the Villa with our five grandchildren, their parents and ourselves, 11 of us. We all fit very comfortably in the Villa. The Villa and pool area, was spotlessly, clean as well as all of the surrounding grounds.There was plenty of space. Giovanna, the owner, ..."

Reviewed on 22 June 2025

Secluded position,villa with private pool,ideal for families, close to Cortona.
Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

3 out of 5
Strada Provinciale 146 di Chianciano, Località Casanova 6/c, San Quirico d'Orcia, SI
Stay at this 3-star residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Horti Leonini and Collegiate ...
9/10 Wonderful! (62 reviews)
"My fiancée and I enjoyed ourselves! It’s a beautiful place and I adored walking around in the nearby town."

Reviewed on 20 July 2025

Casanova - Panoramic Rooms and Suites
See all properties in Castiglion Fiorentino
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Tennis Club Castiglionese

You can take time to visit Tennis Club Castiglionese during your travels to Castiglion Fiorentino. You can enjoy the wineries while in the area.

Tennis Club Castiglionese

Agricola Buccelletti Winery

You can enjoy a tasting or tour at Agricola Buccelletti Winery during your travels to La Strada-Santa Cristina. Discover the area's countryside and wineries.

Agricola Buccelletti Winery

Cassero Tower

Find out about the history of Castiglion Fiorentino when you spend time at Cassero Tower. You can enjoy the wineries while in the area.

Cassero Tower

Archaeological Museum

You can browse the exhibits at Archaeological Museum, a museum with a storied past, during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.

Archaeological Museum

Vasari Loggia

You can find out about the history of Castiglion Fiorentino with a trip to Vasari Loggia. You can enjoy the wineries while in the area.

Vasari Loggia

Municipal Art Gallery

You can study the exhibits at Municipal Art Gallery, a museum with a storied past, during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.

Municipal Art Gallery