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Hotels, Villas, Agriturismos, Bed and Breakfasts, B&Bs, Campgrounds - for the Siena area
Asciano, Casole d'Elsa, Castelnuova Berardenga, Dievole, Molinelli, Montalcino, Monteriggioni, Murlo, Pienza, Poggibonsi, Rapalano Terme

Asciano
Apartments for rent; Villas for rent - from € 350/week

Agriturismo Al Molinello - This Agriturismo is located near Asciano and the spas of Rapolano and the Serre di Rapolano village.  It features a winery and enoteca (wine bar), swimming pool, green area, outdoor children's playground, and other amenities.
Casole d'Elsa
Apartments for rent; Villas for rent - from € 650/week

Tenuta Bichi Borghesi - This wonderful farm is 450 ha, half cultivated with cereals, sunflowers, grass and vineyards; the other half composed by forest where is possible to make walks and relax in the swimming pool and enjoy walks in the vicinity.
Apartments for rent; Villas for rent - from € 720/week

Casa al Prato - The 3 apartments for rent are completely independent, with private entrances, and small terraces. All of them are equipped with heating, air conditioning and private parking.  There is a pool for common use, and guests have access to gardens etc.
Apartments for rent - residence hotel

Borgo Al Cerro - Featuring just 15 self-catering and apartments this residenc hotel is a great place from which you can explore the Maremma to the south, Siena, Voterra, San Gimignano and many other towns, villages and hamlets in this largely untraveled and untrammeled area.
Castelnuovo Berardenga
Apartments for rent; Villas for rent  ~recommended~

Montalto Castle - 4 separate villas and 5  apartments in fully restored castle and in adjacent medieval hamlet - offers simple country elegance - gorgeous setting in Chianti wine country near Siena; private entrances, garden, pool.
Villa for rent - from USD $950/week - 2 bedrooms, sleeps 3

Lo Strettoio - Apartment l'Olivo - Creative design has allowed for the original features to be reserved and the furnishings are modern.A spacious, furnished terrace is used by both apartments and has a large sun shade. A swimming pool is also available.
Dievole (near Siena)
Apartments for rent; Villas for rent

Agricola Dievole - A cypress lined road leads you through eight hundred acres of majestic hill country to Agricola Dievole, a beautiful  private estate in the Chianti region near Vagliagli.  Thereare two villas and many lovely apartments for discerning visitors.
Molinelli
Villa for rent - from USD $2200/week - 3 bdrms, sleeps 7

La Bucaccia - hidden away in what seems like a lost valley. Delightfully private and peaceful, the valley is terraced and is dissected by a stream. The traditional stone house itself is independent has no less than five seating areas, several of which overlook the valley.
Montalcino
Bed and Breakfast; B&B - from € 595/week

Tenuta Friggiali - This air conditioned Villa residence offers an exquisite hospitality in its nineteenth-century structure which has been recently restored, close to the wineries and vineyards where the renowned Brunello and Rosso di Montalcino are refined and bottled.
Monteriggioni
Villa for rent - from USD $4240/week - 8 bedrooms, sleeps 8-15

Villa Il Termine - Enjoy the grandeur of 18th century Italy in this gracious Villa, lavishly furnished with 18th and 19th century antiques, candelabras and paintings. It has always been owned by the present family who are famous wine producers.

Villa for rent - from USD $2280/week - 5 bdrms, sleeps 6-9

Cottage Lauro - Having much privacy, this detached house is within its own private and hedged gardens. Surrounded by lawns and trees within a large park, the cottage and lands are owned by one of the regions’ noted wine producers.
Agriturismo; B&B

Azienda Agraria Scorgiano -  a large farm (nearly 500 Hectares), which breeds pigs for the production of some of Tuscany's finest sausages and meat products, sits in the heart of the Chianti region of Tuscany, near the small, walled city of Monteriggioni.

Monte San Savino

Villa for rent - from USD $12,900/week - 11 bdrms, sleeps 22

Castello San Savino -  A long driveway, dramatically lined with centuries-old cypress trees, leads up to the impressive Castello. First built in the Middle Ages, then extended during the renaissance into an aristocratic residence, the Castello is well-situated.

Murlo (near Montalcino and Siena)

Villa for rent - from USD $1640/week - 3 bdrms, sleeps 4-6

Podere Bagnolo - No expense has been spared as living areas, bedrooms and ceilings have been beautifully redecorated in sumptuous blues, reds and pale oranges all arranged in tasteful stripes and panel patterns.

Pienza

Hotel - 3 + stars

Relais Chiostro di Pienza -  a lovely little hotel, with just 37 rooms, is housed in a wonderfully restored and refurbished 15th century convent, complete with cloisters and extremely well-tended gardens and a pool where one can swim, or take the sun.
Hotel - 3 stars

Hotel La Valle - This small, comfortable hotel features wide, bright spacious rooms with comfortable beds and up-to-date furnishings.  Every room is air conditioned and has its own, well appointed private bathroom. 
Villa for rent - 3 bdrms, sleeps 4-6

Villa La Foce - Just out of the fortified town of Monticchiello, in Val D'Orcia, the property is a typical Tuscan-Sienese farmhouse of the 16th century surrounded by vineyard, now restored and refurbished to become a high class villa. Minutes away from Siena and Montepulciano.
Villa for rent - 4 bdrms, sleeps 8

Villa Orciavalle - a typical Tuscan farm house of 18th century. The villa is located in the area of Orcia Valley, famous for its gentle hills and Medieval towns.  There are two apartments that can be rented together or separately.

Poggibonsi

Agriturismo - 3 apartments; B&B - € 675/week

Fattoria Piercorto - The fattoria is located near a small village the origins of which can be traced back to an old fortress of the XIIth century.  The property sits on a level ridge, crossed by an old Roman road from which one can see a truly splendid panorama:

Radicondoli

Hotel - 3 stars

Hotel Giogliano - this family run country inn sits in the heart of the Tuscan countryside west of Siena, in a location that offers abundant peace and quiet and an opportunity to explore this off the beaten track area of Tuscany. Nine rooms, pool, gardens, country restaurant and more. 

Rapalano Terme - near the spas

B&B - Luxury rooms

Castello delle Serre - A jewel of the Tuscan countryside, the castello majestically sits at the top of the charming medieval town of Serre di Rapolano. This is the passage into the Crete Senesi, the area that has sparked the worldwide love affair with Tuscany.
Agriturismo - 3 apartments; B&B - € 625/week

Podere del Pereto - about 2 km far from Rapolano Terme and the Spas.  Ancient documents testify that the farmhouse already existed in 1372 and was owned by the Monte Oliveto Maggiore Abbey.  It has 3 apartments and one bedroom on B&B basis.
Agriturismo - 3 apartments; B&B - € 625/week

Villa Buoninsegna - The farm takes his name from the big XVIIth Century Villa, with its noble architecture, built in the centre of the estate.  There are other smaller, stone buildings also renovated for travelers.  In total there are 5 apartments and 2 pools.
Agriturismo - 5 apartments - from USD $860/week



 

Podere Le Coste
Encircled by lovely scenery, Podere le Coste, with five apartments, was once a resting house for riders making the journey between Rapolano Terme and Sinalunga. Rent one, several or all.

Apartment Fiorella
2 bedrooms - sleeps
4
from USD $1210/week

Apartment Bella Vista
1 bedroom - sleeps 3
from USD $860/week

Apartment Bosco
1 bedroom - sleeps 3
from USD $860/week

Apartment Terrazza
1 bedroom - sleeps 3
from USD $860/week

Apartment Forno
1 bedroom - sleeps 3
from USD $860/week

Villa for rent - 4 bedrooms

Villa Zeferrelli - The villa is part of Vergelle’s old school building, and was fully renovated in 2008. The property is a large 4 bed-roomed house, over 2 floors and provides excellent accommodation for up to 8 people.  Quiet, private...and good value for money.

Ribolla - between Siena and Grosetto

Villa for rent



Fattoria di Casavecchia - These 18th century farm buildings have been wonderfully restored and offer excellent, comfortable holiday accommodation.

Cerretaia 1 
3 bdrms - sleeps 6
from USD $1420/week

Cerretaia 2
3 bdrms - sleeps 6
from USD $1420/week

Cottage Canonica
2 bdrms - sleeps 4
from USD $1420/week

Macchietta 1
2 bdrms - sleeps 4
from USD $1060/week

Macchietta 2
2 bdrms - sleeps 4
from USD $760/week

Macchietta 3
2 bdrms - sleeps 4
from USD $1060/week

Vecchio Podere 1
2 bdrms - sleeps 4
from USD $1060/week

San Sano

Villa for rent - from $1240 USD/week - 1 bedroom, sleeps 3

Casa Simone - within a mature, wooded and completely fenced garden reached by electrically operated gates. There are very pleasant views through the fruit trees and over vineyards. It has a furnished terrace and the garden has a barbecue.

Siena and immediate vicinity

Hotel - 5 star

Residenza d'Epoca Palazzo Coli Bizzarini - This historical building is known for its simple yet elegant architecture.  With just 4 rooms for the discerning traveler, it is an ideal place for a very comfortable stay in Siena, close to the Campo di Fiori and other ancient monuments.
Hotel - 5 star

Hotel Montaperti - Close to the site of an historic battle, the Montaperti Hotel is built on a hill overlooking the city of Siena. One hundred windows look out towards Siena; there are 16 mini apartments and 80 rooms, either Standard, Superior, or Suite.
Hotel - 4 star

Hotel Palazzo dei Priori - Though located outside the medieval walls of Siena, the hotel is in an ideal position for major connections to highways/the motorway. The city centre is fairly easy to reach by public transport.
Hotel - 4 star (near Siena)

Villa Scacciapensieri - Just 2.5 km from the ancient walls of Siena, this country hotel is located in a grand 19th century Villa.  It boasts 3 luxurious suites and a variety of comfortable, well-appointed rooms.  The restaurant Altri Tempi is deluxe!
Hotel - 3 star

Hotel Chiusarelli - The property is a neo-classic style villa with frescos, which was built in 1870 and completely refurbished according to the original style. The hotel offers many services including a bar, a restaurant, parking facilities and ADSL Internet point.
Hotel - 3 star

Hotel Antica Torre - with just 8 lovely rooms, this hotel is within the ancient walls of Siena and a quick walk to all the main piazzas, buildings, monuments and shopping areas.  The rooms are air conditioned, with private bathrooms.  Great value! 
Hotel - 3 star

Hotel Santa Caterina - Located in a nicely renovated 18th century villa just outside Siena's Porta Romana, this 22 room hotel is a refined and comfortable place to stay while you are in this fabulous Tuscan city.  A little more expensive than some, but worth it!
Hotel - 3 star

Hotel Cannon D'Oro - The Hotel has a rich history. Until 1262, it was a former palace owned by the noble Bulgarini family. Afterwards the building was owned by Ghinibaldo di Saracino and his wife Sapia Salvani, featured in Dante's “Divine comedy”.
Hotel - 3 star

Residenza d' Epocha Palazzo Fani Mignanelli - Situated in the very historical centre of Siena, a few minute walk from Piazza del Campo, relax and comfortable rooms make the Residenza d’Epoca the ideal place to enjoy art and history in Siena.
Agriturismo; B&B; Apartment for rent

Agriturismo Il Lucherino - Just outside the medieval town walls overlooking Siena. The 5 comfortable, well-furnished apartments are simple in their design but refined in character.  They each have lounges with television, a fully-equipped kitchen etc
Villa for rent - from € 6750/week - 10 bedrooms, sleeps 21

Villa Monte 1 - a charming luxury villa for holiday rental in a panoramic position overlooking the surrounding scenic valley of Tuscany, Italy. This luxury villa and its annex offer accommodation for 21 guests and an array of amenities sure to please.
Villa for rent - from $4310 USD/week - 8 bedrooms, sleeps 14

Villa Santo - Comprising of three floors, the property is enriched with superb views of the rolling hillside, a lovely private garden and a refreshing pool. For relaxing with a good book or dining outside al fresco, there is a large patio equipped with table and chairs.
Villa for rent - from € 1285/week - 2 bedrooms, sleeps 3

Terraza Cottage at Villa Monte - Tuscany cottage in Bucine, Siena with a huge sunny terrace on a lovely wine producing estate nestled in the hills between Chianti and the crete of Siena.  Can be rented with Villa Monte 1 and Apartment Libreria.
Apartment for rent - from € 1110/week - 1 bedrooms, sleeps 3

Libreria Apartment Siena, Tuscany - fireplace

Apartment Libreria at Villa Monte -  Everything has been considered to the last detail with a lot of hand work, and ornaments and deluxe upholstering. The main room opens out to a large and very private terrace of 30 sq. mts.
Villa for rent - from USD $1780/week - 3 bedrooms, sleeps 6

Villa delle Stelle - Just ten kilometres from Siena centre, it is immersed in very pretty countryside. There are seven apartments in the Villa delle Stelle each with its own lawns,  garden and furnished outside eating area.
Villa for rent - from USD $1700/week - 3 bedrooms, sleeps 6

Villa I Carpini - This immense, solid and elegant Villa has a private driveway and a vast, hedged garden having some naturally shaded areas under mature pine trees. Between the trees are some unbeatable views over to the city of Siena.
Villa for rent - from USD $1010/week - 2 bedrooms, sleeps 4

Casina delle Rose - an independent, country house in the middle of the historical centre of the quaint, tiny village of Vagliagli. It has a well-established garden and has a large terrace from which are gorgeous vistas over the Chianti Classico countryside.
Apartment for rent



Casa Gabriella - The Podere is an antique farmhouse situated on a hilly area at the doors of Siena. The walls of Siena are about 1,5 km. away. At the same distance are also a riding school, several restaurants and a swimming-pool.

Fienile Apartment
Sleeps 1-3 people
Prices range from 100 E/night

Parata Apartment
Sleeps 1-3 people
Prices range from 100 E/night

Tinaia Apartment
Sleeps 1-4 people
Prices range from 120 E/night

Bed and breakfast

B&B Gli Angeli - located 1 km from the "Siena Sud" exit on the highway for Grosseto, Florence and Arezzo. The center of Siena is just 2 km away and easily reached by car in 5 minutes or with the frequent minibus service.
Trequanda
Villa for rent - 8 bedrooms, sleeps 16

Villa La Contessa - perched on a hill overlooking the countryside and the towns of Siena, Montalcino and Mount Amiata. Still owned by descendants of the original nobility, this magnificent Villa has been newly renovated

Val D'Orcia (see also Pienza and Montalcino)
Hotel - 3 star

Hotel San Simeone - ocated in the village of Rocca d'Orcia in Val d'Orcia a magnificent corner of Tuscany in the Province of Siena.  With just 10 rooms, 4 suites and 4 apartments for longer term stays, this hotel is a rare Tuscan gem.

Villa for rent - 5 bedrooms, sleeps 14
Villa Ciglieglo - a wonderful, beautifully-appointed farm house situated on a hill near  the medieval hamlet of Monticchiello in Tuscany with a breathtaking view of the Valley of Orcia.  The Villa has two separate buildings — the main farm house and a smaller annex.