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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.

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.

 


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.

 


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.

 


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.

 


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.

 


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.

 


TS10 - Villa Tarugi

  Montepulciano , Siena

Sleeps 8
4 Bedrooms
4 Baths

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.

 


TS15 - The Nobleman's House

  Siena area , Siena

Sleeps 8
4 Bedrooms
4 Baths
$4,464 - $7,684

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. Situated on the edge of a medieval village, step out your front door and a short stroll leads you to your morning cappuccino and listen to the church bells ring. 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.

 


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.

 


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.

 


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.

 


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

 


TS16 - Podere Giulio

  Pianella , Siena

Sleeps 10
5 Bedrooms
5 Baths

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.

 


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!

 


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

 


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.

 


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!

 


TS20 - Capanna Poderosa

  Chianti Area , Siena

Sleeps 12
6 Bedrooms
5 Baths

Capanna Poderosa is living its second life from an ancient castle's grain storage building to an open concept Italian villa rental nestled on 50 acres of vineyards and woods. A great home base, being just 25 minutes to Siena, 10 minutes to a quianit village with two restaurants, and 20 minutes from Castelnuovo Bernardegna where you will find supermarkets, banks and a variety of shops. Within 1 hour you can reach Pienza and the val d'orcia, Arezzo and Cortona and even Lake Trasimeno in Umbria. Florence is 90 minutes and the major villages along the chianti wine road can be reached within 20 to 40 minutes.

 


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.

 


TS13 - La Chiantina

  Outside of Radda in Chianti , Siena

Sleeps 10 + 2
5 Bedrooms
6 Baths

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.

 


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.

 

 
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