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Villas in Castiglion Fiorentino

Discover the hidden charm of Tuscany! Find your perfect villa in Castiglion Fiorentino, where medieval streets meet rolling hills & warm Italian hospitality.

Villas in Castiglion Fiorentino

Beautiful private villa for 18 people with ABeautiful private villa for 18 people with A/C, WIFI, hot tub, private pool, TV, patio and parking/C, WIFI, hot tub, private pool, TV, patio and parking
£1001  night
18
9
10
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Tuscany holiday rental
£833  night
16
9
11
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Casale Fonteluccia - Two Bedroom Villa, Sleeps 4
£393  night
4
2
2
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Burone
4.2/5
£74  night
6
2
1
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San Pietro in Polvano
£731  night
21
9
11
Details View Offers
COPPA DI SOPRA - Beautiful villa with superb view
5.0/5
£150  night
6
6
6
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Fiordaliso
4.3/5
£71  night
4
1
1
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Casa White - Holiday Home with private pool and big garden near Castiglion Fiorentino, in Tuscany
5.0/5
£622  night
12
5
3
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VILLA SERENA x6 Beautiful villa surrounded by nature, with swimming pool just 1 km from Cortona
£640  night
6
1
3
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Belvilla by OYO Villa Vittoria
£769  night
8
5
5
Details View Offers
Beautiful private villa for 4 people with ABeautiful private villa for 4 people with A/C, private pool, WIFI, TV and parking, close to Cort.../C, private pool, WIFI, TV and parking, close to Cort...
4.8/5
£120  night
4
1
1
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Stone farmhouse with private swimming pool, hilly, panoramic and quiet position, surrounded by silve
4.0/5
£115  night
5
2
2
Details View Offers
Private Villa with WIFI, private pool, APrivate Villa with WIFI, private pool, A/C, TV, patio, panoramic view, parking, close to Cortona/C, TV, patio, panoramic view, parking, close to Cortona
5.0/5
£808  night
21
11
10
Details View Offers
Independent villa. Pool, fintness area, AirCo, Wi-fi
£385  night
13
6
5
Details View Offers
Le Volpaie 6+1, Emma Villas
5.0/5
£618  night
7
4
2
Details View Offers
Agri-Tourism Le Capanne, Castiglion Fiorentino-Oli
4.3/5
£121  night
4
2
1
Details View Offers
Villa Colle degli Ulivi with pool in Tuscany
£395  night
14
7
6
Details View Offers
Romantic Lux Country House
4.9/5
£600  night
8
3
3
Details View Offers
Silvestro, 3 bedroom converted church villa with pool in vineyard 3K to Cortona
5.0/5
£185  night
5
3
2
Details View Offers
Beautiful private villa with WIFI, private pool, ABeautiful private villa with WIFI, private pool, A/C, TV, veranda and parking, close to Cortona/C, TV, veranda and parking, close to Cortona
5.0/5
£198  night
10
4
3
Details View Offers

Why a holiday villa in Castiglion Fiorentino

Castiglion Fiorentino is a charming hilltop town in Tuscany, Italy, that offers a unique and authentic Italian experience for those who visit. Surrounded by rolling hills, vineyards, and olive groves, this medieval village provides a peaceful retreat from the hustle and bustle of city life.

From your villa base, you can explore the narrow streets and alleys of Castiglion Fiorentino, taking in the historic architecture, visiting the 11th-century church, and enjoying the local cuisine at one of the many traditional trattorias. You can also visit nearby Florence, Siena, and Arezzo to experience the rich art, history, and culture that Tuscany has to offer. With its picturesque landscapes, warm Italian hospitality, and relaxed atmosphere, Castiglion Fiorentino is the perfect destination for a villa holiday in Italy.

Castiglion Fiorentino is also an ideal base for outdoor activities such as hiking, biking, and horseback riding through the Tuscan countryside. You can explore the local markets to buy fresh produce, wine, and olive oil, or simply relax in your villa with a glass of Chianti and enjoy the stunning views.

In addition, Castiglion Fiorentino has a range of excellent restaurants serving traditional Italian cuisine, including ribollita, pappa al pomodoro, and cantucci con vin santo. The town also hosts various festivals throughout the year, such as the Festa di San Lorenzo in August, which features live music, food stalls, and fireworks.

Whether you're looking for a relaxing getaway or an action-packed adventure, Castiglion Fiorentino offers something for everyone. With its unique blend of history, culture, and natural beauty, it's the perfect destination for your Italian villa holiday.

When to rent a villa in Castiglion Fiorentino

Castiglion Fiorentino is a Tuscan town with a Mediterranean climate, characterized by hot summers and mild winters. If you're looking for warm weather without the crowds, consider visiting in September or October when the temperatures are pleasant (22-25°C/72-77°F) and the days are long. These months offer an ideal time for outdoor activities like hiking, biking, and exploring the local countryside.

If you prefer milder weather and don't mind the possibility of some rain, spring (April-May) or autumn (September-October) might be the best times to visit Castiglion Fiorentino. The temperatures are generally cooler than in summer, with highs around 20-22°C (68-72°F), making it perfect for walking tours and exploring the historic center. Winters, from December to February, can be cool and rainy, but if you're looking for a peaceful and relaxed atmosphere, this might be an excellent time to visit Castiglion Fiorentino. Just keep in mind that some local businesses, like restaurants and shops, may have reduced hours or be closed during the winter months.

Where to go in Castiglion Fiorentino

Castiglion Fiorentino is a hilltop town with several districts to choose from for your villa holiday. The historic center, with its narrow streets and medieval architecture, is perfect for those who want to experience the authentic Italian charm of this charming town. However, if you're looking for a more relaxed atmosphere, consider staying in the nearby countryside, where villas are surrounded by olive groves, vineyards, and rolling hills. This area offers peaceful walks, horseback riding, and cycling opportunities, making it ideal for those seeking a tranquil retreat.

For a more vibrant experience, head to the town's outskirts, where you'll find larger villas with private pools and gardens. These areas are often close to local amenities like shops, restaurants, and bars, and offer easy access to nearby Florence, Siena, and Arezzo. Some districts also have beautiful views of the surrounding countryside, making them perfect for villa stays that combine relaxation and exploration. Wherever you choose to stay in Castiglion Fiorentino, be sure to explore the local markets, try the regional cuisine, and soak up the warm Italian hospitality that this enchanting town has to offer.

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Family friendly villas
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Private pool villas
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Villas near golf course
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Villas in Castiglion Fiorentino

Beautiful private villa for 18 people with ABeautiful private villa for 18 people with A/C, WIFI, hot tub, private pool, TV, patio and parking/C, WIFI, hot tub, private pool, TV, patio and parking
£1001  night
18
9
10
Details View Offers
Tuscany holiday rental
£833  night
16
9
11
Details View Offers
Casale Fonteluccia - Two Bedroom Villa, Sleeps 4
£393  night
4
2
2
Details View Offers
Burone
4.2/5
£74  night
6
2
1
Details View Offers
San Pietro in Polvano
£731  night
21
9
11
Details View Offers
COPPA DI SOPRA - Beautiful villa with superb view
5.0/5
£150  night
6
6
6
Details View Offers
Fiordaliso
4.3/5
£71  night
4
1
1
Details View Offers
Casa White - Holiday Home with private pool and big garden near Castiglion Fiorentino, in Tuscany
5.0/5
£622  night
12
5
3
Details View Offers
VILLA SERENA x6 Beautiful villa surrounded by nature, with swimming pool just 1 km from Cortona
£640  night
6
1
3
Details View Offers
Belvilla by OYO Villa Vittoria
£769  night
8
5
5
Details View Offers
Beautiful private villa for 4 people with ABeautiful private villa for 4 people with A/C, private pool, WIFI, TV and parking, close to Cort.../C, private pool, WIFI, TV and parking, close to Cort...
4.8/5
£120  night
4
1
1
Details View Offers
Stone farmhouse with private swimming pool, hilly, panoramic and quiet position, surrounded by silve
4.0/5
£115  night
5
2
2
Details View Offers
Private Villa with WIFI, private pool, APrivate Villa with WIFI, private pool, A/C, TV, patio, panoramic view, parking, close to Cortona/C, TV, patio, panoramic view, parking, close to Cortona
5.0/5
£808  night
21
11
10
Details View Offers
Independent villa. Pool, fintness area, AirCo, Wi-fi
£385  night
13
6
5
Details View Offers
Le Volpaie 6+1, Emma Villas
5.0/5
£618  night
7
4
2
Details View Offers
Agri-Tourism Le Capanne, Castiglion Fiorentino-Oli
4.3/5
£121  night
4
2
1
Details View Offers
Villa Colle degli Ulivi with pool in Tuscany
£395  night
14
7
6
Details View Offers
Romantic Lux Country House
4.9/5
£600  night
8
3
3
Details View Offers
Silvestro, 3 bedroom converted church villa with pool in vineyard 3K to Cortona
5.0/5
£185  night
5
3
2
Details View Offers
Beautiful private villa with WIFI, private pool, ABeautiful private villa with WIFI, private pool, A/C, TV, veranda and parking, close to Cortona/C, TV, veranda and parking, close to Cortona
5.0/5
£198  night
10
4
3
Details View Offers