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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.

TPS101 - Villa Isidoro

  Northeast of Siena , Siena

Sleeps 12
7 Bedrooms
7 Baths
$9,750 - $13,650

Deal from the owner, any available week in 2017 is now 10% less

Villa Isidoro is the perfect Tuscan farmhouse experience while not compromising on luxury. It uses only renewable energy throughout. Understated elegance offers you a country style home in ultimate comfort. Ideally located within twelve miles of San Gimignano and Colle val d'Esa, you are within 30 minutes to Siena, 45 minutes to Florence, Volterra is 20 minutes and Pisa 1 hour 30 minutes. Nearby are many charming hill towns and vineyards of Chianti, including Tuscany's sandy beaches.

 


TS01 - Villa Isabella

  Paurano , Siena

Sleeps 25 to 35 Guests
18 Bedrooms
22 Baths
$37,812 - $51,562

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.

 


TS02 - Villa Romanza

  Southwest of Siena , Siena

Sleeps 22 + 4
11 Bedrooms
11 Baths

Ultimate luxury in breathtaking Tuscany! Enjoy world class cuisine created from the organic gardens, partake of fine Italian and international wines found in your private cellar and schedule regular spa treatments, all handled with impeccable service and attention to every detail. Experience sheer indulgence at this private, exclusive resort-like retreat!

 


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.

 


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.

 


TS05 - Villa di Campagna

  Val d'Orcia , Siena

Sleeps 12 + 2
7 Bedrooms
6 Baths
$6,890 - $11,886

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

 


TS06 - Casaccio di Arte

  Val d'Orcia , Siena

Sleeps 16 + 3 Children
8 Bedrooms
8 Baths

Great for families! This large house is spacious inside and out. Located in the picturesque countryside with exceptional beauty.

 


TS07 - 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.

 


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

 


TS09 - Il Collegio

  Val d'Orcia , Siena

Sleeps 12
6 Bedrooms
6 Baths
$8,125 - $19,500

Spend this summer in Tuscany

30% discount on any available weeks in 2017

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.

 


TS10 - Villa Tarugi

  Montepulciano , Siena

Sleeps 8
4 Bedrooms
4 Baths
$3,177 - $6,423

Villa Tarugi is situated in between the Renaissance town of Montepulciano and the medieval town of Cortona yet just16 miles from Pienza 30 miles from Umbria towns. Perfect location for day trips throughout Tuscany and visiting Umbria as well.

 


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!

 


TS1227 - Villa La Luna

  Southwest of Siena , Siena

Sleeps 27
14 Bedrooms
18 Baths
$28,958 - $38,610
Short Stays

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.

 


TS13 - La Chiantina

  Outside of Radda in Chianti , Siena

Sleeps 10 + 2
5 Bedrooms
6 Baths
$4,225 - $7,943

La Chiantina is centrally located in the heart of Chianti Classico wine region. Located off the famous Chianti wine road, you are within 1 hour from Florence and 40 minutes from Siena. Being in the heart of this region offers you many opportunities to stroll and explore the many Medieval villages, castles and walled towns in the area.

 


TS14 - Casa dal Cuore

  Val d'Orcia , Siena

Sleeps 10
5 Bedrooms
4 Baths
$4,837 - $5,642

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

 


TS15 - The Nobleman's House

  Siena area , Siena

Sleeps 6 + 2
3 Bedrooms
4 Baths
$3,900 - $6,500

This elegant and sophisticated town house sits on a quiet piazza an the edge of a charming 13th century village. This ancient house was originally known as a palazzo signorile, or noble's or gentleman's house. Today the new owner has restored it to a darling luxurious villa. Step out your front door and a short stroll leads you to your morning cappuccino. In the late afternoon, relax in your own private gardens with small plunge pool, terraces and pretty views. Centrally located, with easy day tripping to Montepulciano, Montalcino, Pienza and numerous quaint villages, as well as a 45 minute drive to Siena.

 


TS16 - Podere Giulio

  Pianella , Siena

Sleeps 10
5 Bedrooms
5 Baths
$9,344 - $11,099

Built in the 12th century as a watchtower for a nearby castle, the house has spectacular views of olive groves, vineyards and forests. Just 7 miles from Siena this villa rental is also convenient to many famous wineries. Beautiful swimming pool, SKY TV and many ammenities.

 


TS17 - Villa Vista Grande

  San Casciano dei Bagni Area , Siena

Sleeps 12 + 2
7 Bedrooms
7 Baths
$13,780

This sophisticated Villa is a classic stately home located on a mountain side just 2 miles from the quaint medieval village of San Casciano dei Bagni and a 10 minute drive to the famous Fonteverde Spa. Sprawling lawns, fenced in pool gorgeous views that go on forever , you are 45 minutes from Pienza and Montepulciano, one and a half hours from Siena, Florence and Orvieto.

 


TS18 - Villa Dipinti

  Near Cetona, Val d'Chiana , Siena

Sleeps 10
5 Bedrooms
5 Baths
$14,511 - $17,956

Villa Dipinti is a peaceful luxury retreat set on a hillside with bird's eye views of the surrounding Val d'Chiana valley. You are close to the charming hill towns of Cetona, Montepulciano and San Casciano dei Bagni. This home has been lovingly restored by the owner into a gracious and tranquil space that includes all the luxury elements of a fine villa. It is the perfect villa for those that want a truly relaxing place to call home while enjoying all that Tuscan living offers. Your cares will be whisked away with the gentle breeze the moment you arrive. Luxury with an understated elegance and overwhelming charm. Fully Air Conditioned.

 


TS19 - Villa Tommaso

  Near Siena , Siena

Sleeps 12
6 Bedrooms
5 Baths

Originally a manor house for noble families to escape from the city during the hottest months of summer, now a vacation paradise in the heart of 'Chianti Senese'. Only ten miles from Siena.

 


TS21 - Pascolo

  Pienza , Siena

Sleeps 20
8 Bedrooms
8 Baths
$18,330 - $24,863
Short Stays

High on a hilltop in the picturesque area of Val d'Orcia, 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.

 


TS22 - Villa Leonora

  Val d'Orcia Area , Siena

Sleeps 8
5 Bedrooms
5 Baths

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.

 


TS23 - Villa Giacomo

  Pienza , Siena

Sleeps 8
4 Bedrooms
4 Baths
$7,735

Half way between Montalcino and Montepulciano, two of Italy's famous wine production areas. This luxury farmhouse is well appointed with the amenities of a five star hotel. . Just a few minutes drive to Pienza,you are immersed in the peaceful countryside.

 


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.

 


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.
Priced Euro 6,480 per night for the nine bedroom manor house.

 

 
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