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Luxury Villas in Castiglione d'Orcia, Tuscany

Discover the charm of Tuscany's hidden gem, Castiglione d'Orcia, where luxury villas meet breathtaking views. Explore medieval streets, vineyards, and olive groves, and make unforgettable memories in this enchanting corner of Italy.

Villas in Castiglione d'Orcia

Podere Ginestra - Four Bedroom Villa, Sleeps 8
£704  night
8
4
5
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Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany
4.8/5
£794  night
20
9
11
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Appartamento Vista Tramonto
4.5/5
£86  night
2
1
1
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Villa Dezi
4.8/5
£377  night
8
4
4
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Villa Corsini - Tuscan country villa with swimming pool
£293  night
8
4
2
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Villa Castiglione - Holiday Farmhouse with private swimming pool in Val d'Orcia, Tuscany
5.0/5
£661  night
15
7
8
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Villa Fioranna, cosy house in the olive grove - Podere Bellaria
5.0/5
£129  night
6
3
2
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Villa with Pool in Maremma
£260  night
8
3
2
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Stunning private villa for 4 guests with pool, WIFI, TV and parking
5.0/5
£238  night
4
2
2
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Villa BelSentiero in the Val d'Orcia with infinity pool. Sleeps 10 in 5 rooms
5.0/5
£943  night
10
5
5
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Casale Olivastra
5.0/5
£432  night
8
4
4
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Farmhouse 'Villa Agriturismo Il Pratone' with Mountain View, Private Pool and Wi-Fi
4.8/5
£245  night
6
3
2
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Villa D'Orcia - Homelike Villas
£593  night
15
6
6
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Villa Cassia - Holiday Country House with private swimming pool in Val d'Orcia, Tuscany
5.0/5
£249  night
8
4
4
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'...a delicious farmhouse in the countryside where only the wind blows...'
5.0/5
£686  night
16
6
7
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Stunning villa with WIFI, private pool, TV, panoramic view and parking, close to Montepulciano
£258  night
8
4
4
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Casale d'Orcia In Castiglione d'orcia - Tuscany
5.0/5
£606  night
16
6
6
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Beautiful Villa Casa di Giulio in Viterbo
£270  night
5
3
2
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Sant'Alberto, Castiglione d'Orcia, Siena and Chianti
£705  night
12
6
6
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Villa San Michele - Villa with swimming pool in Orcia Valley, Tuscany
5.0/5
£402  night
6
3
4
Details View Offers

Why a holiday villa in Castiglione d'Orcia

Castiglione d'Orcia is a hidden gem waiting to be discovered, and what better way to experience its charm than from the comfort of your own luxury villa? Nestled in the heart of Tuscany's rolling hills, this picturesque town offers breathtaking views, rich history, and authentic Italian culture. Imagine waking up to the sound of birds singing, surrounded by vineyards and olive groves, with a private pool and breathtaking views just steps away.

As you explore Castiglione d'Orcia, you'll discover charming streets lined with medieval architecture, quaint shops, and cozy trattorias serving up delicious local cuisine. Visit ancient castles, wine cellars, and art galleries, or take a leisurely stroll through the surrounding countryside, enjoying the region's famous sunsets and starry night skies. In the evenings, retreat to your luxurious villa, where you can relax with loved ones, enjoy a glass of wine, and make unforgettable memories in this enchanting corner of Italy.

When to rent a villa in Castiglione d'Orcia

When it comes to planning your villa holiday in Castiglione d'Orcia, timing is everything. The region's Mediterranean climate means that the best time to visit is during the spring and early autumn when the weather is mild and pleasant. From March to May, the area awakens from its winter slumber, with gentle temperatures ranging from 15°C to 20°C (59°F to 68°F) and plenty of sunshine. This is an ideal time to explore the town's historic center, visit local vineyards, and enjoy outdoor activities like hiking or biking.

If you prefer warmer weather, July and August are peak summer months in Castiglione d'Orcia, with temperatures often reaching highs of 25°C (77°F) and lows of 15°C (59°F). However, be prepared for larger crowds and higher prices during this period. For a more relaxed atmosphere, consider visiting in the shoulder season, from September to November or April to June, when the weather is still pleasant but the tourist rush has subsided. Whatever your preference, Castiglione d'Orcia's villa rentals are available throughout the year, so book your perfect retreat and make the most of your Tuscan getaway.

Where to go in Castiglione d'Orcia

As you search for the perfect villa in Castiglione d'Orcia, consider basing yourself in the town's historic center. This charming area is filled with narrow cobblestone streets, picturesque piazzas, and ancient architecture, making it a haven for those seeking a romantic getaway or a relaxing retreat. Visit the medieval castle, explore the local shops and markets, and indulge in delicious meals at one of the many authentic trattorias. If you're looking for a more relaxed atmosphere, consider renting a villa in the surrounding countryside, where you can enjoy breathtaking views, peaceful walks, and stunning sunsets.

For those seeking a more vibrant experience, head to the nearby town of Montalcino, known for its stunning views, charming streets, and world-class wine. Visit the famous Brunello di Montalcino winery, take a hot air balloon ride over the rolling hills, or simply enjoy a leisurely lunch at one of the many cozy restaurants. Alternatively, explore the picturesque villages of Sant'Angelo in Colle or San Quirico d'Orcia, where you can discover hidden gems, charming streets, and breathtaking views. Whatever your preference, Castiglione d'Orcia has something to offer, making it an ideal destination for your villa holiday.

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Villas in Castiglione d'Orcia

Podere Ginestra - Four Bedroom Villa, Sleeps 8
£704  night
8
4
5
Details View Offers
Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany
4.8/5
£794  night
20
9
11
Details View Offers
Appartamento Vista Tramonto
4.5/5
£86  night
2
1
1
Details View Offers
Villa Dezi
4.8/5
£377  night
8
4
4
Details View Offers
Villa Corsini - Tuscan country villa with swimming pool
£293  night
8
4
2
Details View Offers
Villa Castiglione - Holiday Farmhouse with private swimming pool in Val d'Orcia, Tuscany
5.0/5
£661  night
15
7
8
Details View Offers
Villa Fioranna, cosy house in the olive grove - Podere Bellaria
5.0/5
£129  night
6
3
2
Details View Offers
Villa with Pool in Maremma
£260  night
8
3
2
Details View Offers
Stunning private villa for 4 guests with pool, WIFI, TV and parking
5.0/5
£238  night
4
2
2
Details View Offers
Villa BelSentiero in the Val d'Orcia with infinity pool. Sleeps 10 in 5 rooms
5.0/5
£943  night
10
5
5
Details View Offers
Casale Olivastra
5.0/5
£432  night
8
4
4
Details View Offers
Farmhouse 'Villa Agriturismo Il Pratone' with Mountain View, Private Pool and Wi-Fi
4.8/5
£245  night
6
3
2
Details View Offers
Villa D'Orcia - Homelike Villas
£593  night
15
6
6
Details View Offers
Villa Cassia - Holiday Country House with private swimming pool in Val d'Orcia, Tuscany
5.0/5
£249  night
8
4
4
Details View Offers
'...a delicious farmhouse in the countryside where only the wind blows...'
5.0/5
£686  night
16
6
7
Details View Offers
Stunning villa with WIFI, private pool, TV, panoramic view and parking, close to Montepulciano
£258  night
8
4
4
Details View Offers
Casale d'Orcia In Castiglione d'orcia - Tuscany
5.0/5
£606  night
16
6
6
Details View Offers
Beautiful Villa Casa di Giulio in Viterbo
£270  night
5
3
2
Details View Offers
Sant'Alberto, Castiglione d'Orcia, Siena and Chianti
£705  night
12
6
6
Details View Offers
Villa San Michele - Villa with swimming pool in Orcia Valley, Tuscany
5.0/5
£402  night
6
3
4
Details View Offers