All our Vacation Rentals in Montalcino
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Villa
Hedoné Retreat Private villa in San Terenziano Umbria 5 bedrooms | 5 bathrooms | Up to 16 guests | Private saltwater ...
- Garden
- Near Village
- Maid Service
- Parking
- Bike
- Swimming Pool
Special Offers
Book your vacation for the period from 08 June 2026 to 31 March 2027 and save 10% (minimum 7 nights).
Book your vacation for the period from 08 June 2026 to 31 March 2027 and save 15% (minimum 14 nights).
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Villa
Villa Isaia is a prestigious historic residence nestled in the Chianti hills, in a panoramic location between Florence and Siena, with stunning views of the Tuscan countryside and the city of Siena. Dating back to the 15th century and carefully renovated between 1996 and 1998, the property combines historic charm, luxury, and modern comforts, offering an exclusive experience in a setting of absolute privacy. The villa is surrounded by a large, well-kept, centuries-old garden with scenic paths, relaxation areas, and shaded corners. The outdoor spaces include a large private swimming pool (14 x 7 m) equipped with sun loungers, a gazebo, and a solarium area, a tennis court, a hot tub, as well as several areas dedicated to outdoor recreation and relaxation. Villa Isaia can be booked in its entirety and is ideal for large groups, private events, or high-end stays. The main property has 16 bedrooms, all with private bathrooms, air conditioning, and unique architectural features. Upon request, it is also possible to include the annex and the owner's apartment, accommodating up to 35 people in total. The interiors offer numerous common areas: large halls, living rooms, a fully equipped professional kitchen with access to a large outdoor terrace for lunches for up to 36 guests, relaxation rooms, an entertainment area, and a private chapel. Each room is designed to ensure comfort, elegance, and functionality. The stay includes high-level service with dedicated staff, daily breakfast, cleaning, concierge service, and the possibility of organizing lunches and dinners with a private chef. The villa is strategically located for visiting Siena, Florence, San Gimignano, Monteriggioni, Volterra, and the main destinations in Tuscany. Villa Isaia is a prestigious solution for those who want to experience the splendor of Tuscany in an exclusive historic residence surrounded by nature and served with standards of excellence.
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- Baby Bed
- Restaurant
- Parking
- Swimming Pool
- Tennis Court
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Villa
Located a short distance from Gaiole in Chianti, Villa Ghirlanda is a private residence nestled in the heart of Chianti Classico, surrounded by vineyards, hills, and iconic landscapes. Access is via a picturesque tree-lined driveway that leads to a setting of absolute tranquility and authentic Tuscan charm. The villa is surrounded by a private garden of approximately 4,000 m², carefully tended and enriched with plants, flowers, and antique terracotta jars. Outside, there is a private swimming pool (8 × 4 m), perfectly integrated into the landscape and ideal for relaxing outdoors. The outdoor spaces are designed to allow guests to enjoy the villa at any time of day, surrounded by sunshine, silence, and nature. The property is spread over two levels with a total area of approximately 400 m² and can accommodate up to 12 people. It has 6 double bedrooms and 5 bathrooms. The interiors maintain a rustic and elegant character, with traditional furnishings, stone fireplaces, large convivial tables, and a fully equipped kitchen. The rooms are spacious and functional, suitable for group or family stays. Wi-Fi is available, and some rooms are equipped with air conditioning. A distinctive feature of the villa is its direct link to the wine-making tradition of the area: the owner is a wine producer and, on request, it is possible to organize visits to the cellar and private tastings for an authentic experience in the heart of Chianti. Villa Ghirlanda is a private vacation rental, not a hotel. It is particularly suitable for families or groups of friends who want a stay immersed in nature, silence, and the culture of Chianti, with Siena, medieval villages, and the main Tuscan destinations within easy reach.
- Garden
- Internet
- Baby Bed
- Parking
- In Village
- Next Year Available
per Night
Villa
Villa Pianoro is an elegant panoramic residence nestled in the rolling hills of Radda in Chianti, in the heart of the most authentic Chianti region. Surrounded by vineyards and olive groves, it dominates a picture-postcard landscape of neat rows of vines, cypress trees, and ancient stone houses, in one of the most iconic areas of Tuscany, famous throughout the world for its great wines and the timeless atmosphere of its medieval villages. An ancient lookout point overlooking the valley, the villa has been carefully rebuilt, integrating modern technology and contemporary comforts while fully respecting the original structures. Stone arches, vaulted ceilings, wooden beams, and large windows tell the centuries-old story of the property, now reinterpreted with a fresh and essential design that harmoniously blends rustic style and modern details. The outdoor spaces are designed to allow guests to fully enjoy the view: the kitchen opens onto a patio with a barbecue, pizza oven, and outdoor dining area, while the garden features a heated swimming pool, a play area, and relaxation areas equipped with sun loungers and parasols. On the opposite side, a furnished gazebo offers an intimate corner for breakfast and dinner surrounded by the tranquility of the hills. The fully fenced estate produces award-winning wines and excellent olive oil, which are featured in tastings dedicated to guests. Inside, spacious and bright rooms include living rooms with fireplaces, a professional kitchen, a wellness area with Turkish bath, a fully equipped gym, and five double bedrooms with private bathrooms, as well as additional spaces for families and children. With services included such as buffet breakfast, daily cleaning, aperitif, and welcome dinner, Villa Pianoro is an exclusive retreat for experiencing Chianti in total comfort and authenticity.
- Garden
- Near Village
- Internet
- Maid Service
- Baby Bed
- Swimming Pool