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Siena Province, Tuscany
 

A very beautiful and varied landscape awaits you in this province. Once a thriving area constantly at war with Florence, the plague in the 13th century wiped out most of its inhabitants and the area fell into neglect. Because of this lost interest, the province of Siena did not develop as quickly as the others and we are fortunate in that it has resulted in changing little from those medieval days. Restoration began centuries later and it is now one of the most sought after locations in Tuscany. This is an area famous for its cypress trees originally planted to provide shelter from the wind along roads leading to the owner's homes they are now an important and very recognizable feature of this landscape as they stand against the backdrop of low-rolling clay hills. San Gimignano, Monteriggioni, San Galgano, Montalcino, San Quirico d'Orcia, Bagno Vignoni, Asciano, Pienza, Montepulciano are just a few of the many well preserved towns that are easily accessed from all areas of this province.


Showing 1 to 25 of 48 results. Page  1 2 Next
Properties are listed in order by Reference Number. The properties can also be sorted by the number of Sleeps or the City location. Venice, Florence and Rome are sorted by area when you request a sort by City. Click again to reverse order of sort.

TS64 - Angelica

  Val d'Orcia , Siena

Sleeps 34
17 Bedrooms
17 Baths

Five exquisite and individual Tuscan villas comprise this restored 11th century medieval borgo. Magical setting, with incredible views of the Val di Chiana valley. Perfect for families to gather together, yet the meticulously maintained gardens and footpaths between the properties offer privacy. Resort-like services, including a restaurant for those days you don't feel like cooking in your professional Tuscan kitchen.

 


TS63 - Le Quattro Case

  Val d'Orcia , Siena

Sleeps 26
13 Bedrooms
13 Baths

Le Quattro Case (The Four Houses) is comprised of Villa Messalina, Casa Jolanda, Casa Teodoro and Cottage Virginia, four of five exquisite and individual Tuscan villas in this restored 11th century medieval borgo. Magical setting, with incredible views of the Val di Chiana valley. Resort-like services, including a restaurant for those days you don't feel like cooking in your professional Tuscan kitchen.

 


TS62 - Le Tre Case

  Val d'Orcia , Siena

Sleeps 16
8 Bedrooms
8 Baths

Le Tre Case (The Three Houses) is comprised of Casa Jolanda, Casa Teodoro and Casa Rafaello, three of five exquisite and individual Tuscan villas in this restored 11th century medieval borgo. Magical setting, with incredible views of the Val di Chiana valley. Resort-like services, including a restaurant for those days you don't feel like cooking in your professional Tuscan kitchen.

 


TS61 - Villa Messalina and Cottage Virginia

  Val d'Orcia , Siena

Sleeps 14
7 Bedrooms
7 Baths

Two of five exquisite and individual Tuscan villas in this restored 11th century medieval borgo. Magical setting, with incredible views of the Val di Chiana valley. Resort-like services, including a restaurant for those days you don't feel like cooking in your professional Tuscan kitchen.

 


TS60 - Casa Jolanda and Casa Teodoro

  Val d'Orcia , Siena

Sleeps 12
6 Bedrooms
6 Baths

Two of the five exquisite and individual Tuscan villas in this restored 11th century medieval borgo. Magical setting, with incredible views of the Val di Chiana valley. Resort-like services, including a restaurant for those days you don't feel like cooking in your professional Tuscan kitchen.

 


TS59 - Casa Rafaello

  Val d'Orcia , Siena

Sleeps 4
2 Bedrooms
2 Baths

One of five exquisite and individual Tuscan villas in this restored 11th century medieval borgo. Magical setting, with incredible views of the Val di Chiana valley. Resort-like services, including a restaurant for those days you don't feel like cooking in your professional Tuscan kitchen.

 


TS58 - Villa Messalina

  Val d'Orcia , Siena

Sleeps 8
4 Bedrooms
4 Baths

One of five exquisite and individual Tuscan villas in this restored 11th century medieval borgo. Magical setting, with incredible views of the Val di Chiana valley. Resort-like services, including a restaurant for those days you don't feel like cooking in your professional Tuscan kitchen.

 


TS57 - Casa Teodoro

  Val d'Orcia , Siena

Sleeps 6
3 Bedrooms
3 Baths

One of five exquisite and individual Tuscan villas in a restored 11th century medieval borgo. Magical setting, with incredible views of the Val di Chiana valley. Resort-like services, including a restaurant for those days you don't feel like cooking in your professional Tuscan kitchen.

 


TS56 - Casa Jolanda

  Val d'Orcia , Siena

Sleeps 6
3 Bedrooms
3 Baths

One of five exquisite and individual Tuscan villas in this restored 11th century medieval borgo. Magical setting, with incredible views of the Val di Chiana valley. Resort-like services, including a restaurant for those days you don't feel like cooking in your professional Tuscan kitchen.

 


TS55 - Cottage Virginia

  Val d'Orcia , Siena

Sleeps 6
3 Bedrooms
3 Baths

One of five exquisite and individual Tuscan villas in this restored 11th century medieval borgo. Magical setting, with incredible views of the Val di Chiana valley. Resort-like services, including a restaurant for those days you don't feel like cooking in your professional Tuscan kitchen.

 


TS54 - Villa Falco Nero

  Le Crete , Siena

Sleeps 20 + 2
10 Bedrooms
10 Baths

A dreamy villa behind a private gate and long driveway assures your privacy. The setting consists of a large spacious villa with 8 bedrooms and cottage with 2 additional bedrooms. A very large swimming pool sits among spacious lawns on a wine estate makes it an ideal retreat for families as well of group of friends wanting to spend a relaxing time in the heart of the Montepulciano wine area. RENTS SUNDAY TO SUNDAY

 


TS53 - Caprioli

  San Casciano dei Bagni , Siena

Sleeps 9 + 1
5 Bedrooms
5 Baths

19th century country home with annex is completely restored, blending Tuscan charm with modern comforts. Relax by the pool and enjoy the views!

 


TS5210 - Casa di Andrea

  Le Crete , Siena

Sleeps 10
5 Bedrooms
5 Baths
$4,424 - $7,272

Set among olive groves and spacious lawns surrounded by Pomegrante trees and bay laurels, this luxury style farmhouse ensures privacy yet within walking distance to a charming village with small shops, banks and restaurants. Within half an hour you can be exploring the romantic village of Pienza, tasting Super Tuscans in Montepulciano and Montelcino, listening to Gregorian Chants in an ancient monestary all in the most picturesque areas of Tuscany

 


TS5016 - Villa Contenta

  Le Crete , Siena

Sleeps 16
8 Bedrooms
7 Baths

Villa Contenta in the Siena area of Tuscany has beautiful grounds and unbelievable views of the Siena countryside. While the town is quite intimate, it has all the necessities including a coffee bar, two truffle and wine bars, and the Tartuffo museum. The front door of this 15th century villa faces an ancient village hamlet while the back of the house has a 180 degree view of rolling hills and tall cypress trees indigenous to the famous Le Crete countryside. The place to stay to really experience Tuscany at her finest. Can be rented with Casa Federica for a total of twenty-one guests.

 


TS49 - Bella Caterina

  Le Crete , Siena

Sleeps 21 + 1 child
11 Bedrooms
9 Baths

The best of both worlds! The feel of living in the countryside with the convenience of living in town. Located in a small hilltop village, the front door faces the main street of the village, while the back of the property offers you outdoor living spaces with 180 degrees of beautiful views of the magnificent Le Crete countryside.

 


TS48 - Brunello

  Montalcino , Siena

Sleeps 5
3 Bedrooms
2 Baths

A heavenly retreat for wine aficionados, this little cottage is tucked away in the heart of Italy's famous wine producing area near Montalcino, home of the King of Italian red wines, Brunello di Montalcino. Breathtaking views from the center of a twenty-five acre vineyard.

 


TS46 - Podere Casciano

  Val d'Orcia , Siena

Sleeps 11
6 Bedrooms
7 Baths

Warm, comfortable home with 1 bedroom guest house situated amidst the splendid rolling hills of the Val d'Orcia and waving fields of lavender. Perfect for families to enjoy everything Tuscany has to offer, including the hot springs and thermal baths found near San Casciano. Walk to town and the famous Fonte Verde Spa. The home is well positioned to tour all of Tuscany, including Siena, Montepulciano and Florence, perfect for day trips. Return home in the afternoon and relax by the pool, which is fed by a naturally warm spring – your own private thermal bath!

 


TS45 - Borgo Vecchio - Cottage Federico

  Le Crete , Siena

Sleeps 10
5 Bedrooms
5 Baths

Five Star Luxury Property in the heart of what many say is the most beautiful area of Tuscany. Just 25 miles southwest of Siena.
Priced Euro 3,000 per night.

 


TS44 - Borgo Vecchio - Cottage Teresa

  Le Crete , Siena

Sleeps 8
4 Bedrooms
4 Baths

Five Star Luxury Property in the heart of what many say is the most beautiful area of Tuscany. Just 25 miles southwest of Siena.
Priced Euro 2,400 per night.

 


TS43 - Borgo Vecchio - Cottage Fillipo

  Le Crete , Siena

Sleeps 4
2 Bedrooms
2 Baths

Five Star Luxury Property in the heart of what many say is the most beautiful area of Tuscany. Just 25 miles southwest of Siena.
Priced Euro 1,200 per night.

 


TS42 - Borgo Vecchio - Cottage Calussa

  Le Crete , Siena

Sleeps 4
2 Bedrooms
2 Baths

Five Star Luxury Property in the heart of what many say is the most beautiful area of Tuscany. Just 25 miles southwest of Siena.
Priced Euro 850 per night.

 


TS41 - Borgo Vecchio - Manor House

  Le Crete , Siena

Sleeps 18
9 Bedrooms
9 Baths

Once upon a time, Borgo Vecchio was the center of a medieval Tuscan village. Today, the nine bedroom manor house and cottages accommodating up to 44 people near Buonconvento is an up-to-date gathering place, its 14th-century foundations supporting an event space for fifty, teaching kitchen, media room, gym and Jacuzzi. Book the Borgo for an unforgettable event, use it as a base to explore the area around Montalcino, or simply treat yourself to pampering by the villa's staff.
Price Starting at Euro 6,480 per night for the nine bedroom manor house.

 


TS40 - Borgo Vecchio

  Le Crete , Siena

Sleeps 44
22 Bedrooms
22 Baths

Once upon a time, Borgo Vecchio was the center of a medieval Tuscan village. Today, the twenty-two bedroom manor house and cottages near Buonconvento is an up-to-date gathering place, its 14th-century foundations supporting an event space for fifty, teaching kitchen, media room, gym and Jacuzzi. Book the Borgo for an unforgettable event, use it as a base to explore the area around Montalcino, or simply treat yourself to pampering by the villa's staff.
Priced Euro 13,930 per night.

 


TS31 - Il Castello

  Val di Chiana , Siena

Sleeps 14
7 Bedrooms
7 Baths

Steeped in history, this villa sits on the highest point of a charming medival village offering you spectacular views of the Tuscan countryside. Surrounded by your own private park like setting with formal garden, your days are filled with tranqulity as well as the convenience of village life below. Centrally located for touring Tuscany and Umbria.

 


TS26 - Villa Francesco

  Val D'Orcia , Siena

Sleeps 13
7 Bedrooms
6 Baths

This luxurious home sits on fifty acres with panoramic views of the Val d'Orcia. Beautifully appointed and completely private with gated entrance yet ideally located for day trips. Close to town, train station and the main autostrada, it is as close to perfection as it gets. This very special home has been featured in several magazines and books.

 

 
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