The picturesque undulating hills and valleys of the Siena territory, characterized by medieval hill villages, are home to our Luxury Villas in Siena.
Siena territory is central Tuscany, world-renowned for its fine wine, delectable olive oil, and charming hilltop communities. A splendid fresco with its rolling hills, magnificent cypress trees, precise rows of vineyards, and silver olive groves.
The Chianti wine region is home to some of the best wine estates in the world, producing rich, dark Chianti wines. The area is also home to some of the most beautiful towns in Italy, including San Casciano, Panzano, Greve in Chianti, Radda in Chianti and San Gimignano).
Crete Senesi, to the south, is named from the clay hills that produce a stark and barren environment (with the walled town of Montalcino and its world-famous Brunello wine). Pretty hilltop communities abound, connected by long winding roads ideal for leisurely sightseeing and peaceful contemplation.

Siena is a well-preserved example of Tuscan Middle Ages architecture. The city (UNESCO World Heritage Site) is home to several Gothic palaces, churches, and museums loaded with Gothic art. It is situated on seven hills and features narrow cobblestone streets and alleyways.
Siena strikes you as a place locked in time the moment you see it; since the 1300s, Siena’s streets have hardly changed.
The spectacular fan-shaped Piazza del Campo is the beating canter of the city’s old parishes, who battle against one another in the famed Palio (dating back to 1310). Palio is a heady mix of medieval pomp, ceremony, and passion, ending in a frantic, bareback horse race around the Campo. The city’s principal attractions are crammed into a maze of narrow medieval alleyways near the square. The unique black and white striped cathedral and the majestic medieval Torre del Mangia are unmissable.

Luxury mansions and stone farmhouses with breath-taking views of the countryside and the stars sky above the beautiful swimming pools are among our Siena villas. We offer huge, renovated farmhouses in the Tuscan hills that are ideal for a family gathering. Almost all of our villas in Siena feature air conditioning, which you’ll appreciate during the long, hot summers in Tuscany.
A holiday in Siena in one of our villas with private pools is more than just a holiday rental; it ensures you will experience the authentic Tuscan way of life.

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Villa Dorian

Siena - Montalcino Area From: €5,320 to: €9,520 per week

Villa Dorian is an amazing villa for 10 guests in Montalcino area, famous worldwide for wines production. A large and private pool in the garden fro exclusive u...

  • Elegant villa in Montalcino area, famoous for wines production
  • Large and private pool surrounded by the green vegetation
  • Amazing furnishings
  • 10 Sleeps
  • 5 Bedrooms
  • 5 Bathrooms
  • Pool

Poggio alle Mura 100m-0,06miles
Castello Banfi 6Km-3,7miles
Grosseto 45Km-27miles
Marina di Grosseto 60Km-37miles
Siena 65Km-40miles

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Casale Montalcino

Montepulciano-Siena From: €5,880 to: €10,010 per week

A stunning countryside villa with private and exclusive pool in Toscana, only 9Km to Montepulciano and other fantastic cities.

  • Stunning villa with private pool
  • Private suites for a complete privacy
  • Garden and well equipped outside spaces
  • 11+1 Sleeps
  • 6 Bedrooms
  • 6 Bathrooms
  • Pool

Montalcino downtown 9Km-5,5miles
Grosseto 46Km-28miles
Parco della Maremma 63Km-39miles
Siena 66Km-41miles
Arezzo 92Km-57miles

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Villa Orange

Siena - Montalcino Area From: €6,370 to: €10,360 per week

If you're looking for an holiday in real Tuscany mood, Villa Orange, an old restored cascina with private pool, finally is the eprfect location for yo and your ...

  • Elegant villa in countryside
  • Spectacular views from the garden and from the house
  • Private pool and manor courtyard for exclusive use
  • 12 Sleeps
  • 6 Bedrooms
  • 5 Bathrooms
  • Pool

Castello Banfi 3,6Km-2,2miles
Poggio alle Mura 3,7Km-2,9miles
Grosseto 47Km-29miles
Marina di Grosseto 62Km-38miles
Siena 67Km-41miles