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 AED 1,656 per night from Jun 22 to Jun 23
AED 1,656
AED 1,847 total
22 Jun - 23 Jun
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. ...
9.2/10 Wonderful! (87 reviews)
"This is a beautiful location and the facilities are stunning. Really everything is picture perfect and you are only 20 minutes from Montepulciano and 30 minutes from Pienza. Both are amazing to explore and offer excellent dining options. The concierge recommended Tuscan Sweet Dreams to take us to ..."

Reviewed on 8 April 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 AED 2,299 per night from Jul 6 to Jul 7
AED 2,299
AED 2,563 total
6 Jul - 7 Jul
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! (208 reviews)
"Simply outstanding in every aspect. The staff are incredible, especially Blurton was outstanding."

Reviewed on 4 June 2025

Villa di Piazzano - Small Luxury Hotel of the World
See all 6,735 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
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 spa residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Horti Leonini and Collegiate ...
9/10 Wonderful! (54 reviews)
"Excellent views and the property was overall lovely. The nearby town San Quirico d'Orcia also had a good selection of restaurants and was a nice place to stroll in the evening."

Reviewed on 4 June 2025

Casanova - Panoramic Rooms and Suites
Hotel San Gregorio
Hotel San Gregorio
3 out of 5
Via Della Madonnina 4, Pienza, SI
Stay at this 3-star business-friendly residence in Pienza. Enjoy free WiFi, an outdoor pool, and 2 hot tubs. Popular attractions RI Crea RE and Enoteca Di Ghino ...
"Fabulous location just outside the entrance to the main part of town. Property is stylish in an olde worlde way, perfect for relaxation."

Reviewed on 18 April 2025

Hotel San Gregorio
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

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

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