All our Vacation Rentals in Montalcino
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Villa
Villa Tessaroni: Luxurious Tuscan Retreat in Val d'Elsa Nestled in the heart of the Val d’Elsa, in the scenic Siena region, lies Villa Tessaroni, a 16th-century farmhouse meticulously restored by the Eriksen Tellier family over the past five years. This exquisite estate provides a luxurious and authentic Tuscan experience, combining historic charm with modern comforts, all set amidst the picturesque landscapes of the region. A Glimpse into the Past: History and Heritage Villa Tessaroni stands as a testament to the rich cultural heritage of the Val d’Elsa. The farmhouse retains its traditional charm, offering guests a glimpse into Tuscany’s past while ensuring modern comforts and amenities. The main casale and annex are restored in a way that harmoniously blends old-world elegance with contemporary living, providing a unique and memorable experience. Accommodations and Amenities Villa Tessaroni can accommodate up to 22 guests, making it ideal for large families, corporate retreats, or gatherings of friends. The estate comprises the main casale and an annex, offering a total of eight ensuite rooms, including: - Main Casale: - One master suite with a California King bed. - Four ensuite rooms with King beds. - One ensuite room with two full beds. - One Tower Room, accommodating 2 to 4 children under 10 years old, but without a bathroom. - Annex: - Two ensuite rooms with King beds. - One mezzanine loft with two single beds, complete with a bathroom with a shower. All rooms in the casale and annex are ensuite, ensuring complete privacy and comfort. The estate also offers various services and amenities, including: - **Housekeeping:** Two hours per day, with linen and towel changes mid-week or upon request. - **Utilities:** Up to 100 kW/day of electricity and 100 m³/lt/day of water. - **Catering:** Cook services for up to 25 guests are available upon request, offering breakfast, lunch, dinner, brunch, and even pizza parties. - **Spa:** An indoor/outdoor plunge pool with massaging waterjets, a sauna, and a hammam (Turkish bath). - **Gym:** A state-of-the-art gym equipped with Technogym machines, including a treadmill, elliptical, and spin-cycle. - **Event Space:** A versatile 457 m² indoor space with panoramic views, a chef’s kitchen, and outdoor terrace seating for up to 400 guests. - **Outdoor Pool:** A 22-meter pool with a plunge zone and massaging water jets, along with landscaped gardens and a pizza oven adjacent to the main kitchen.
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Villa
Hedone Retreat — A Restored Stone Casale in the Umbrian Hills Set in the quiet folds of the Umbrian countryside, just outside ...
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Special Offers
Book your vacation for the period from 08 June 2026 to 28 December 2029 and save 10% (minimum 7 nights).
Book your vacation for the period from 08 June 2026 to 31 March 2029 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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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.
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- Next Year Available
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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.
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