Villa Simone is a beautiful historic villa located in the heart of the Chianti hills, just a few kilometers from the picturesque town of San Gimignano.
This luxurious stone mansion dates back to the 15th century and stands in a panoramic position offering breathtaking views of the surrounding countryside.
The villa was built around a watchtower, a feature that gives it a unique charm and a touch of history.
Despite its ancient origin, Villa Simone was completely renovated in 2023, respecting its original architectural features but adding the modern comforts necessary for a luxurious stay.
The villa has been tastefully furnished, following the typical rustic Tuscan style, which is reflected in the wooden furniture, fabrics and architectural details such as exposed beams and terracotta floors.
The villa can accommodate up to 14 people thanks to its seven bedrooms, making it an ideal choice for groups of friends or large families wishing to vacation together.
Outside, Villa Simone offers a large manicured garden, perfect for relaxing and enjoying the tranquility of the countryside.
The private swimming pool, equipped with deck chairs and umbrellas, is the perfect place to cool off during hot summer days.
For sports enthusiasts, a tennis court is also available.
In addition, there is an outdoor diningarea, where guests can enjoy al fresco meals surrounded by the beauty of the Tuscan landscape.
Villa Simone is the perfect destination for a relaxing and enjoyable vacation surrounded by nature and the historic Chianti countryside.
With its combination of historic charm and modern comforts, this villa offers an unforgettable experience in one of Italy’s most fascinating regions.
The amenities for those staying at Villa Simone
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The exteriors feature a large terraced garden, enhanced by outdoor furniture and a ping-pong area, as well as beautiful Italianate gardens dating back to the 18th century, adorned with lemon trees.
The facility also offers a reception desk open during set hours and outbuildings converted into lovely apartments, run with passion by the Posarelli family. To complete the experience, the castle boasts an excellent restaurant serving traditional Tuscan cuisine.
The rich and fertile soil, together with the favorable climate, creates ideal conditions for growing the vines from which Chianti, a red wine that has gained international fame and appreciation, is made. But Chianti is not only synonymous with food and wine excellence; it is also a land rich in history. Castles, parishes and medieval villages dot the area, bearing witness to centuries of conflict, trade and daily life that shaped this region. The Chianti hills offer breathtaking scenery, with their winding roads winding between rows of vines and cultivated fields, providing picture-postcard scenery at every turn. This land is a permanent invitation to exploration for both nature lovers and history and culture enthusiasts. Walks and hikes on foot, bicycle or horseback allow you to fully immerse yourself in the unspoiled beauty of the area, discovering hidden corners and unforgettable views. Life in the Chianti hills flows slowly, respectful of the seasons and the traditions that have guided the lives of its inhabitants for generations. Daily activities are often linked to the land and its cycles, with the grape harvest in the fall and the olive harvest in the winter marking the rhythm of rural life. The people of Chianti are custodians of an invaluable cultural and gastronomic heritage, always ready to share the secrets of their land with visitors through festivals, tastings and meetings. Castello di Montegufoni is nestled in this idyllic setting, providing an ideal starting point for exploring the riches of Chianti. Its privileged location makes it possible to enjoy the serene beauty of the Tuscan landscape while experiencing firsthand the history, art, and food and wine traditions that have made this region world famous.
During the summer months, the village’s only shop/shop is transformed into a meeting place for locals and visitors, offering dinners that are true celebrations of Tuscan cuisine.
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The area is equipped for relaxation and entertainment, allowing guests to enjoy the Tuscan sunshine in complete privacy and comfort.
The villa can comfortably accommodate up to 12 or 13 people in 6 bedrooms, making it ideal for large families or groups of friends. The interiors are equipped with all modern amenities such as Wi-Fi and air conditioning, ensuring a relaxing and comfortable stay.

Surrounded by lush forests, the villa allows guests to fully experience the serene and relaxingatmosphere typical of the Italian countryside, with views extending to the surrounding rolling hills.
Villa Margherita Uno offers an interior space of 80 m², distributed on two floors, combining functionality with the warmth of rustic Tuscan design. Spaces are optimized for comfort and convenience, making the villa an ideal place for a relaxing vacation in the countryside.
This level includes:
Adjacent to the pool is a barbecue area with a pergola, table, and benches, perfect for holding barbecues and enjoying outdoor meals while enjoying the view and tranquility of the place.
The villa, surrounded by a lush garden full of local flowers and plants, is the ideal place for those seeking tranquility and privacy.
Villa Ulivi and its annex, La Casina, offer luxuriously appointed interiors that combine rustic Tuscan charm with modern conveniences, creating warm and welcoming environments for an unforgettable stay.
The First Floor is dedicated to conviviality with an open-plan kitchen and living room, as well as an additional bathroom with shower. The furnishings are carefully selected to reflect the warmth andaesthetics of the region, with exposed wooden beams and Tuscan-style floors adding a touch of rustic authenticity.
The property is easily accessible via a 2.5-kilometer dirt road that meanders through the Tuscan countryside, offering breathtaking panoramic views along the way that anticipate arriving at this dream location. The villa’s strategic location allows guests to explore famous locations such as Volterra, San Gimignano, Siena, Florence and the Tuscan coast with ease.
Villa Picchio offers two separate but integrated apartments, both carefully designed to ensure comfort and privacy. Each apartment measures 70 m² and is equipped with modern conveniences, furnished to reflect the warmth and style of Tuscany.
This outdoor space is perfect for hosting recreational activities or simply spending quality time outdoors.