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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 26 to 48 of 48 results. Page  Previous 1 2
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.

TS1227 - Villa La Luna

  Southwest of Siena , Siena

Sleeps 27
14 Bedrooms
18 Baths
$26,442 - $35,245

Fully staffed to take care of your every whim, you will be totally pampered at this Tuscan villa located twenty-five kilometers south of Siena. Perfect for weddings, celebrations, multi-generation villa vacations or just a group of friends. Full spa, indoor and outdoor swimming pools, conservatory, observatory, gardens, fishing ponds, forests and a nearby horse stable for experienced riders.

 


TS04 - Palazzone

  Val D'Orcia , Siena

Sleeps 10 + 1
5 Bedrooms
6 Baths

This farmhouse has stood high on a hill for over 300 years, with magnificent views of the Val di Chiana valley. Elegant yet comfortable, a wonderful place to call home for awhile.

 


TS14 - Casa dal Cuore

  Val d'Chiana , Siena

Sleeps 10
5 Bedrooms
4 Baths
$4,362 - $7,499

This beautiful charming country house is right out of a fairy tale. Completely private, with gated entrance, sitting on 5 acres you are immersed in the beautiful landscape of the val di Chiana with views of the Val d'Orcia. Solitude yet the nearest village of 750 is just under 2 miles away where you will find a restaurant and grocery store. Easy day trips to Siena, Pienza, Montepulciano, Cortona

 


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.

 


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.

 


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.

 


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.

 


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.

 


TS03 - Zibetto

  Val d'Orcia , Siena

Sleeps 10
5 Bedrooms
5 Baths

The stunning 300 year old stone farmhouse, surrounded by cherry trees, oak trees, lavender and scented shrubbery has been carefully restored by one of Italy's premier furniture and home designers and her architect husband. You will find their creative interior home designs gracing the covers of coffee table books and magazines.

 


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!

 


TS09 - Il Collegio

  Val d'Orcia , Siena

Sleeps 12
6 Bedrooms
6 Baths

Conveniently located on edge of a wonderful Tuscan village, yet surrounded by gardens to ensure your privacy. The English designer created a Zen like atmosphere in her extensive restoration of a former school. Walk to town, nearby Spa and natural hot water springs. Attentive staff. All rooms on one floor centered around an exquisite outdoor living area with large heated swimming pool and picturesque views of the Val d'Orcia.

 


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.

 


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.

 


TS05 - Villa di Campagna

  Val d'Orcia , Siena

Sleeps 12 + 2
7 Bedrooms
6 Baths
$9,887 - $13,842

Villa di Campagna is a very unique family friendly home has the luxury of a villa yet an enveloping comfort of a country farmhouse set in the countryside. Beautifully restored, the interior is awash in soft colors and a winsome décor that will keep you smiling and fill you with warmth. You are truly home. Ideally located in the coveted Val d'Orcia of Southern Tuscany you are within walking distance to town, yet high on a hill offering privacy. Easy day trips to small neighboring towns including Montepulcino, Montalcino, Pienza and Radicofani and easy access to Siena, Florence, and Rome by car or nearby train station. Heated Swimming Pool

 


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.

 


TS11 - Villa Pienza

  Val D'Orcia , Siena

Sleeps 16
8 Bedrooms
6 Baths

A luxurious villa in the heart of the area known as the Val D'Orcia. The landscape of this area is perhaps the best preserved and most beautiful in Tuscany. A professional kitchen for those that enjoy cooking, private park, stupendous views! A wonderful Tuscan experience!

 


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.

 


TS08 - La Frateria

  Val d'Orcia , Siena

Sleeps 18
9 Bedrooms
9 Baths

Luxurious Tuscan villa situated in one of the prettiest areas of the Siena countryside. Enjoy the incredible views and the hospitality of its gracious owners who designed the villa with your complete comfort in mind. Large kitchens, four living rooms, 10,000 square feet of terraces, 52 foot jet stream heated swimming pool and Jacuzzi all with incredible views of dreamy Tuscany

 


TS06 - Casaccio di Arte

  Val d'Orcia , Siena

Sleeps 16 + 3 Children
8 Bedrooms
8 Baths

A modern take on a century old farmhouse with a hilltop setting that offers up panoramic views over some of Italy's most bucolic landscapes. Beautiful outdoor living spaces, heated pool and wood burning pizza oven. Easy drive to the wine territories of Montalcino and Montepulciano.

 


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.

 


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.

 


TS22 - Villa Leonora

  Val d'Orcia Area , Siena

Sleeps 8
5 Bedrooms
5 Baths
$7,719 - $12,564

Situated on 70 acres in the heart of the Unesco World heritage site of the val d'Orcia, you are surrounded by meadows, woodlands, and farmland, Villa Leonora has breathtaking views stretching out over the Val d'Orcia to the Amiata mountains.. A beautiful restoration and well designed formal gardens and heated pool is the perfect mix for a perfect villa vacation.

 


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.

 

 
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