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Chianti Vacation Rentals

Results 1-6 of 6 Properties

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SAL VOL

This beautiful farmhouse is located in a very quiet and secluded position on the Castello di Volpaia estate, where we have successfully been renting two other properties, La Pozza and Il Casetto for many years. The owners of the estate, with long experience in providing guest accommodations, completed restoration of this stone-built farmhouse in 2005. Their aim was to make it the ideal residence for those seeking a totally relaxing holiday in Chianti, so they have provided full-time staff to takecare of the house and to prepare meals for guests. The interior of Casavecchia Volpaia has been restored with full respect for the typical Tuscan traditions, and each bedroom has been equipped with an en-suite bathroom. Guests can enjoy incredible views from the covered terrace, which is furnished for outdoor dining and is also very practical for families as it overlooks the pool, allowing parents to relax while keeping an eye on the pool area. The fortified hamlet of Volpaia offers 2 restaurant owned by the estate. The estate can organize cooking lessons for guests to learn the art of Tuscan cuisine, and an opportunity to visit the wine cellars. The helpful, English speaking staff can organize cooking lessons, visits to the wine cellar, and will be glad to assist guests during their stay. There is a tennis court in the hamlet of Volpai, available upon request. Read More 800.957.7405

  • 4 Bedroom
  • 4 Bath
  • Sleeps 8
  • Pool
  • Accepts:
  • Visa
  • MasterCard
  • American Expres

5 Bedroom Farmhouse in Classic Chianti Hills

Immersed in the classic Chianti hills, only 10 minutes from Siena by car, this beautiful farmhouse enjoys an exceptionally privileged panoramic position. It is located at the top of a hill from which you can admire the open spaces, olive groves, vineyards and woods of the surrounding area. The nearest grocery shops can be found in the village of Pianella, which is only 4 minutes away by car. Built in the 15th century as a watchtower, Monticelli rests on foundations that go back to the 12th century. The villa has 1,5 hectares of enclosed land and an Infinity pool equipped with an exercise jet, a system which allows you to swim against a current. The pergola adjacent to the swimming pool is furnished with wooden sun loungers. Under the swimming pool there is a pool room which has showers both inside and out. In harmony with the spacious and well-equipped kitchen, there is a charming terraced floor connected to the garden, which is furnished for outdoor dining. The living area is well-furnished with traditional country and antique furniture. The bedrooms are decorated in a more simple fashion, furnished with vintage furniture. The bathrooms are finished to a high standard, particularly that of the master bedroom, which has a beautiful bathtub placed in the centre of the room. The villa can be easily reached via a well maintained gravel road. Read More 800.957.7405

  • 5 Bedroom
  • 5 Bath
  • Pool
  • Maid Service
  • Accepts:
  • Visa
  • MasterCard
  • American Expres

SAL CVD

The small, rural hamlet of Volpaia with its fortified walls dating from Medieval times, is one of the best remaining examples of its kind in Tuscany. It is located, just north of Radda in Chianti, in a beautiful position overlooking vineyards and olive groves. The wines produced on the estate of Volpaia are among the best in the Chianti Classico area, and the cellars certainly deserve a visit. Both the red and white wines, together with the olive oil, are marketed as “Castello di Volpaia”, andknown worldwide. The farm also manages the shop and the restaurant of the village, where it is possible to buy all the products that are made locally and to taste the local cuisine. Cooking classes are also arranged, on request, by the local office. The house is built on several levels and has recently been meticulously restored by the owners. A swimming pool has been installed and surrounded by a fence, making it safe for young children. There is also a tennis court right in the centre of the hamlet, within walking distance of the property, available on request. Read More 800.957.7405

  • 4 Bedroom
  • 3 Bath
  • Pool
  • Tennis
  • Accepts:
  • Visa
  • MasterCard
  • American Expres

Casetto di Volpaia

The small, rural hamlet of Volpaia with its fortified walls dating from Medieval times, is one of the best remaining examples of its kind in Tuscany. It is located, just north of Radda in Chianti, in a beautiful position overlooking vineyards and olive groves. The wines produced on the estate of Volpaia are among the best in the Chianti Classico area, and the cellars certainly deserve a visit. Both the red and white wines, together with the olive oil, are marketed as Castello di Volpaia, and knownworldwide. The farm also manages the shop and the restaurant of the village, where it is possible to buy all the products that are made locally and to taste the local cuisine. Cooking classes are also arranged, on request, by the local office. The house is built on several levels and has recently been meticulously restored by the owners. A swimming pool has been installed and surrounded by a fence, making it safe for young children. There is also a tennis court right in the centre of the hamlet, within walking distance of the property, available on request. Guests at Casetto di Volpaia can enjoy a free lesson in the owner's renowned cooking school (for preparing a light lunch to taste all together) or a nice lunch with the owners of the estate. Read More 800.957.7405

  • 4 Bedroom
  • 3 Bath
  • Pool
  • Tennis Court
  • Accepts:
  • Visa
  • MasterCard
  • American Expres

La Maccinaia

La Maccinaia is a beautiful property located in a very quiet location, in the heart of the Chianti region, between Gaiole and Castelnuovo Berardenga. The main villa dates to the 17th century, and has been immaculately restored by its Belgian owner who combined modern design with original Tuscan architecture. The property is equipped with the highest standard of modern comforts, including air-conditioning, wi-fi technology, a large flat screen television with satellite tv, and an especially well equippedkitchen. The bedrooms are furnished with great taste, and almost all of them have en-suite bathrooms. Just across from the main villa there is a guest house built of stone that can sleep up to 6 people. This part of the property is of more recent construction, but maintains the same high level of the main villa. A particular feature is a covered veranda which makes eating al fresco a lovely experience. The panoramic position of La Maccinaia allows guests to enjoy colorful views of the Chianti countryside, especially from the guest house terrace and the pool area. The English speaking caretaker lives on the premises in an apartment with a separate entrance. Read More 800.957.7405

  • 5 Bedroom
  • 5 Bath
  • Pool
  • Maid Service
  • Accepts:
  • Visa
  • MasterCard
  • American Expres

Wimco Villas Rentals on Chianti

Experience the beautiful Chianti region of Tuscany from one of our luxury villas. Wimco offers 15 villas set amongst the rocky Chianti vineyards. Wimco, an industry leader since 1983, has helped thousandsof clients by offering firsthand knowledge of the villas and the villages of Chianti. Visit www.Wimco.com to view our full selection of Chianti villas, check availability and book your villa on-line. Or call to speak to our agents. Read More 800.957.7405

Results 1-6 of 6 Properties

Direct Inquiry to All or Selected Owners/Agents


Find the perfect Chianti vacation rental property with ease! Choose a Chianti property above to view the amenities and rates. If you are interested in one of the many homes, condominiums, hotels or villas that are available in Italy contact the actual property owner direct or be directed to a lodging provider that can best suit your needs for family, group or business accommodation in Chianti
Be sure to click on the banner images above to go to the property where you can view more details of all the accommodations we have to offer. We have a large selection of privately owned and professionally managed villas, condos, hotels, vacation homes and much more. If you have any questions or need help making sure the trip you are planning will be one of the best Chianti vacations you have ever taken. We hope that you find the exact Chianti lodgings that you are looking for at 10,000 Vacation Rentals.
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Remember that contacting the vacation rental owners direct is the best way to get more information on specific vacation homes or condos. However if you are having problems finding what you are looking for, please do not hesitate to call (888) 217-1785.