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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.
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| 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. |
TS01
- Villa Isabella
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Paurano , Siena
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Sleeps 25 to 35 Guests
18 Bedrooms
22 Baths
$27,550 - $46,400
40% DISCOUNT FOR ALL REMAINING WEEKS IN 2010 - FIVE STAR ACCOMMODATIONS from $179 to $265 per person per night!
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One of the most exquisite offerings in Italy. Owned for centuries by an aristocratic family, this is la crème de la crème of villas. No matter how hard we try to describe this luxurious villa we know we will come up short. To immerse yourself in total luxury you also have a staff that includes maids, wait staff, a gardener and your own personal concierge.
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TS03
- Zibetto
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Val d'Orcia , Siena
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Sleeps 10
5 Bedrooms
5 Baths
$8,000 - $12,500
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This elegant home is reached through a private road through the woods and opens up to a gorgeous setting that will take your breath away. |
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TS04
- Palazzone
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Val D'Orcia , Siena
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Sleeps 10 + 1
5 Bedrooms
6 Baths
$8,500 - $13,600
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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. |
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TS05
- Francigena
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Val d'Orcia , Siena
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Sleeps 16
8 Bedrooms
8 Baths
$11,250 - $20,000
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If you want a picture postcard home for your stay in Tuscany, look no further! |
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TS06
- Casaccio di Arte
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Val d'Orcia , Siena
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Sleeps 16 + 3 Children
8 Bedrooms
8 Baths
$11,250 - $20,000
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Great for families! This large house is spacious inside and out. Located in the picturesque countryside with exceptional beauty. |
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TS08
- Redaelli
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Val d'Orcia , Siena
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Sleeps 12
6 Bedrooms
6 Baths
$10,000 - $16,875
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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. |
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TS09
- Rossellino
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Val D'Orcia , Siena
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Sleeps 11
5 Bedrooms
3 Baths
$5,545 - $7,057
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Warm, inviting tradtional Tuscan country house with original features and modern comforts. Completely private with incredible views. Close to Pienza and Montepulciano, while you have your own private lane to reach the house, you have easy access to major roads. Heated Jacuzzi Pool ! and a large non heated Swimming pool! |
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TS10
- Villa Tarugi
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Montepulciano , Siena
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Sleeps 6
3 Bedrooms
3 Baths
$3,120 - $5,520
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Villa Tarugi is situated in between the Renaissance town of Montepulciano and the medieval town of Cortona yet just 28 kms from Pienza. Perfect location for day trips throughout Tuscany and visiting Umbria as well |
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TS11
- Villa Pienza
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Val D'Orcia , Siena
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Sleeps 16
8 Bedrooms
6 Baths
$8,906 - $11,426
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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! |
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TS12
- Villa La Luna
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Southwest of Siena , Siena
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Sleeps 27
14 Bedrooms
18 Baths
$29,000 - $36,250
Short Stays
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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, large groups of family and friends or business meetings. Full spa, indoor and outdoor swimming pools, conservatory, observatory, gardens, fishing ponds, forests and a nearby horse stable for experienced riders. |
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TS13
- Oliva Nero
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Radda in Chianti , Siena
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Sleeps 4
2 Bedrooms
2 Baths
$2,147 - $2,335
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One of two little restored barn located on an olive oil farm between Siena and Florence. Cozy and charming, this house has been restored in typcial Tuscan decor. Lovely English speaking owners live on the property. Free olive oil seminar and tour. In the fall you are invited to help them pick olives! |
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TS14
- Oliva Verde
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Radda in Chianti , Siena
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Sleeps 2
1 Bedrooms
1 Baths
$1,308 - $1,401
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One of two little restored barn located on an olive oil farm between Siena and Florence. Cozy and charming, this house has been restored in typcial Tuscan decor. Lovely English speaking owners live on the property. Free olive oil seminar and tour. In the fall you are invited to help them pick olives!
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TS15
- Casa Nuova
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Val D'Orcia , Siena
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Sleeps 13
7 Bedrooms
6 Baths
$9,125 - $14,375
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This luxurious home sits on fifty acres with panoramic views of the Val dOrcia. 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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TS16
- Podere Giulio
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Pianella , Siena
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Sleeps 10
5 Bedrooms
5 Baths
$9,250
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Built in the 12th century as a watchtower for a nearby castle, the house has spectacular views of olive groves, vineyards and forests. |
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TS18
- Casale Giuggiola
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Siena Outskirts , Siena
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Sleeps 10
5 Bedrooms
4 Baths
$10,887 - $12,960
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Rambling Tuscan farmhouse situated on extensive grounds of a private estate. Just minutes from Siena with easy access to Florence and many Chianti hill towns. Recommended for families as well as friends looking to enjoy their time in the Chianti countryside. |
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TS21
- Pascolo
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Pienza , Siena
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Sleeps 20
8 Bedrooms
8 Baths
$21,750
Short Stays
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High on a hilltop in the picturesque area of Val dOrcia, Pascolo has 360 degree views of the unblemished countryside that everyone dreams of when they think of Tuscany. Not far from the famous and quaint town of Pienza, Pascolo is an old rustic farmhouse that has been lovingly restored mixing the old style Tuscan with a fresh contemporary interior design. |
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TS22
- The Linden Tree
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Cetona , Siena
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Sleeps 16
8 Bedrooms
6 Baths
$8,265 - $10,150
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Southern Tuscany, near Sarteano and Cetona sits this pretty home with a main house and two cottages to sleep a total of sixteen guests. Can also be rented for twelve guests! One mile from two ancient and characteristic villages.
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TS23
- Aprile
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Sarteano , Siena
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Sleeps 7
4 Bedrooms
4 Baths
$3,016 - $4,449
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This villa with an attached mini apartment is surely a comfortable and luxurious home for every season. Offering all modern conveniences, the owner has been very particular in choosing every last detail to ensure Aprile has unique characteristics and is comfortable for guests. |
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TS24
- Capanno Cottage
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Pianella , Siena
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Sleeps 4 + 1
2 Bedrooms
2 Baths
$2,381 - $2,568
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18th century cottage in the middle of the Tuscan countryside where the movie Stealing Beauty was filmed. Carefully restored using original antique Tuscan stones and bricks, chestnut beams and terracotta tiles. Beautiful views, pretty interior, private location. |
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TS28
- Radda di Bassa
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Outside of Radda , Siena
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Sleeps 9
6 Bedrooms
3 Baths
$2,892 - $6,475
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Immensely warm and comfortable, this 15th century farmhouse is situated at the end of a long, cypress-lined driveway and has magnificent views. Rent with nearby Radda di Alta for larger groups. |
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TS29
- Radda di Alta
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Outside of Radda , Siena
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Sleeps 12
7 Bedrooms
5 Baths
$4,742 - $9,367
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Ancient stone farmhouse, recently restored yet still retains its understated character. Great location for touring the famous Chianti wine country. Rent with nearby Radda di Bassa for larger groups. |
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TS30
- Due Case di Radda
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Outside of Radda , Siena
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Sleeps 21
13 Bedrooms
8 Baths
$7,633 - $15,842
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Two farmhouses, beautifully restored in country Tuscan style, on the same estate and situated just outside of Radda in Chianti. |
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TS31
- Bel Soggiorno 1
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San Gimignano Suburb , Siena
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Sleeps 4 + 2
2 Bedrooms
1 Baths
$900 - $1,479
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One of five apartments in a recently restored villa. Located on the hilltop of an estate once belonging to Tuscan royalty with incredible views. Situated in a small hamlet and only four kilometers from the town of San Gimignano. |
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TS32
- Bel Soggiorno 2
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San Gimignano Suburb , Siena
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Sleeps 4 + 2
2 Bedrooms
1 Baths
$900 - $1,479
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One of five apartments in a recently restored villa. Located on the hilltop of an estate once belonging to Tuscan royalty with incredible views. Situated in a small hamlet and only four kilometers from the town of San Gimignano. |
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TS33
- Bel Soggiorno 3
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San Gimignano Suburb , Siena
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Sleeps 3 + 2
2 Bedrooms
1 Baths
$900 - $1,479
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One of five apartments in a recently restored villa. Located on the hilltop of an estate once belonging to Tuscan royalty with incredible views. Situated in a small hamlet and only four kilometers from the town of San Gimignano. |
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