Castiglion Fiorentino

Travel Guide

A historic town with a prominent church tower, surrounded by rolling hills and vineyards.
A rural landscape with fields, trees, and mountains under a partly cloudy sky.
A panoramic view of a valley with a wooden fence in the foreground, dense green foliage, and distant hills under a clear sky.
Photo by Pigellino (Creative Commons Attribution 3.0)
A sunflower field with a town in the background.
Photo by Pigellino (Creative Commons Attribution 3.0)
A dirt path leading to a panoramic view of a valley with scattered buildings and fields.
Photo by Pigellino (Creative Commons Attribution 3.0)
Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.

Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.

Castiglion Fiorentino
Stay at this villa in Castiglion Fiorentino. Enjoy private pools, a garden, and laundry facilities. Popular attractions Agricola Buccelletti Winery and Tennis ...
9.8/10 Exceptional! (40 reviews)
"This villa has breathtaking views and a gorgeous peaceful pool area. We were travelling as a family with our adult children and their partners. We were 7 in total and there was plenty of room for us both outside and in. The kitchen is very well equipped with modern appliances and plentiful dishware. ..."

Reviewed on Jun 14, 2026

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Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10 Montepulciano SI
The price is CA $1,025 per night from Jul 6 to Jul 7
CA $1,025
CA $1,137 total
Jul 6 - Jul 7
includes taxes & fees
Book a stay at this luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.6/10 Exceptional! (147 reviews)
"It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)"

Reviewed on Jun 19, 2026

Precise Tale Poggio Alla Sala
A Point Arezzo Park Hotel

A Point Arezzo Park Hotel

4 out of 5
Loc. Battifolle, 36/T Arezzo AR
The price is CA $129 per night from Jul 2 to Jul 3
CA $129
CA $151 total
Jul 2 - Jul 3
includes taxes & fees
Book a stay at this spa hotel in Arezzo. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Arezzo Equestrian Centre and Memorial of the ...
7.6/10 Good! (165 reviews)
"Well, having travelled extensively for the past 13 years, this Hotel must be the coldest I have ever stayed in. It was December, but there was no heating on in the lobby area or the dining area so everyone had to wear coats or thick jumpers while eating their meals. The showers were not particularly ..."

Reviewed on Dec 3, 2025

A Point Arezzo Park Hotel
See all 6,607 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.
Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.

Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.

Castiglion Fiorentino
Stay at this villa in Castiglion Fiorentino. Enjoy private pools, a garden, and laundry facilities. Popular attractions Agricola Buccelletti Winery and Tennis ...
9.8/10 Exceptional! (40 reviews)
"This villa has breathtaking views and a gorgeous peaceful pool area. We were travelling as a family with our adult children and their partners. We were 7 in total and there was plenty of room for us both outside and in. The kitchen is very well equipped with modern appliances and plentiful dishware. ..."

Reviewed on Jun 14, 2026

Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.
Lovely home in Castiglion Fiorentino

Lovely home in Castiglion Fiorentino

Castiglion Fiorentino
Stay at this vacation home in Castiglion Fiorentino. Enjoy free WiFi, private pools, and a sauna. Popular attractions Cassero Tower and Archaeological Museum ...
Lovely home in Castiglion Fiorentino
Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

3 out of 5
Strada Provinciale 146 di Chianciano San Quirico d'Orcia SI
Stay at this residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Horti Leonini and Chapel of our Lady ...
9.2/10 Wonderful! (91 reviews)
"Everything was great"

Reviewed on May 16, 2026

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.

Stay near popular Castiglion Fiorentino attractions

Tennis Club Castiglionese

Catch an event at Tennis Club Castiglionese during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.
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Things to do

Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

CA $32
per adult
Oil museum and oil mill in Tuscany: tour and tasting
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

CA $40
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Cellar Tour & Wine Tasting

Cellar Tour & Wine Tasting

CA $81
per adult
Cellar Tour & Wine Tasting
See all activities in Castiglion Fiorentino

Cities near Castiglion Fiorentino

A historic square with a central open space, surrounded by colorful buildings with arched windows and a prominent tower.

Arezzo

A hillside town with historic buildings, a church, and vineyards.

Cortona

A stone tower, a curved road, and traditional buildings with a stone wall.

Monte San Savino

An aerial view of a historic town with red-roofed buildings, a prominent tower, and surrounding green fields.

Marciano della Chiana