Luxury rentals in Montalcino

Villa Montemaggio

The Tuscan sun soaks into the stone walls of this 17th-century farmhouse—and into the grapes clustered in the organic vineyards in the surrounding Chianti countryside. The Roman road from Siena to Florence once traced these hills; today, they’re home to the 70-hectare Montemaggio estate, which produces organic wine and olive oil. Siena is 40 minutes away by modern road; Florence, 1 hour. Smell the flowers in the gardens, pick fresh mulberries and figs to snack on, and see if you and the kids can find the playhouse hidden away on the estate’s grounds. There’s a private gym for workouts, a swimming pool for refreshment, and a rooftop terrace just made for the evening’s first bottle of local wine. While the villa still has some of its 17th-century farmhouse charm—spot beamed ceilings, doorways framed in elaborate molding, and a wide hearth on the living room fireplace—it’s been fully renovated. A pair of plump sofas invites you to stay a while in the living room, and there are plenty of chairs around the dining table that takes center stage in the fully equipped kitchen. Learn more about the Montemaggio estate by booking a cooking class, featuring fresh produce from the gardens, or a wine tour. Be sure to ask about the festivals in nearby villages, which range from celebrations of wine to a fete dedicated to bruschetta. Beyond Tuscany’s medieval towns and fortresses, the cities of Siena and Florence are close enough for a day trip. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Dual vanity, Bidet, Television, Desk • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Television • Bedroom 3: Queen size bed, Ensuite bathroom with stand-alone rain shower, Bidet, Television, Desk FEATURES & AMENITIES • More under “What this place offers” below Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Villa Conti Galgani

Located in the heart of the Tuscan countryside, between Florence and Rome, just 70km from Siena, Villa Conti Galgani is a charming estate, immersed in 65 hectares of hilly countryside, among olive groves and gardens. The villa has 7 suites, each characterized by an individual style, inspired by the rich history of the estate. Conti Galgani is the perfect place for those who want to spend a relaxing holiday in the Tuscan countryside, equipped with an outdoor swimming pool, a gym, an indoor hydro-massage pool and a billiard room. Handcrafted furniture and a modern eye for color breathe new life into this 16th-century former convent set between Tuscany’s Val di Chiana and Val d’Orcia. Olive groves and a lawn surround the outdoor pool and for-the-picking vegetable garden, and inside there’s a second pool and a games room. It’s 20 kilometers to Renaissance architecture in Pienza and hot springs in San Casciano dei Bagni. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower, Dual vanity, Bidet, Television, Countryside view • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Bidet, Air extractor, Countryside view • Bedroom 3: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Dual vanity, Bidet, Countryside view • Bedroom 4: Queen size bed, Ensuite bathroom with stand-alone rain shower, Bidet • Bedroom 5: 2 Twin size beds, Ensuite bathroom with stand-alone rain shower, Bidet, Air extractor, Television • Bedroom 6: King size bed, Day bed, Ensuite bathroom with stand-alone rain shower & bathtub, Bidet, Air extractor, Television, Mountain view • Bedroom 7: Queen size bed, Ensuite bathroom with stand-alone rain shower, Bidet STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions

Quercia

Step outside each morning to feel the warm, fresh breeze as you stroll through fruit gardens and forests of oak at this traditional farmhouse estate in the heart of Tuscany. Embark on day trips to nearby villages, vineyards, and the famous Abbey of San Galgano. Return home for an afternoon swim, a delicious alfresco dinner, and a night of incredible Italian wine by the fireplace. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Main House • Bedroom 1 - Primary: King size bed, Ensuite bathroom with shower/bathtub combo, Bidet • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Bidet, Balcony • Bedroom 3: 2 Twin size beds (can be converted to a king), Day bed, Ensuite bathroom with stand-alone rain & steam shower, Bidet House 2 • Bedroom 4: King size bed, Ensuite bathroom with shower/bathtub combo, Bidet, Walk-in closet, Sofa, Desk • Bedroom 5: King size bed, Shared access to hallway bathroom, shower/bathtub combo, Dual vanity, Bidet, Desk • Bedroom 6: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone rain & steam shower, Bidet, Walk-in closet, Desk • Bedroom 7: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone rain shower, Bidet, Walk-in closet OUTDOOR FEATURES • Outdoor living space STAFF & SERVICES Included: • Linen change - twice per week • Concierge service Extra Cost (advance notice may be required): • Activities and excursions • Additional housekeeping

Luxury Villa Justina Tuscany

This unique place has a style all its own. Villa Justina is set on a hill top overlooking 30 acres with 2 wine vineyards and olive groves which makes it a tranquil spot. The furnishings encompasses high end Italian furniture and contemporary art mixing it with antiques making it quite unique. As this villa was recently purchased it features all new luxury bedding, towels, dishes and kitchen ware. The Villa comes with cleaning services and able to cater to the highest level.

Villa Chianti Fornace

Experience the epitome of Tuscan luxury at Villa Chianti Fornace — a meticulously restored historic villa nestled between Florence and Siena. This exquisite retreat features expansive gardens, a private spa, and a panoramic pool with sweeping views of rolling vineyards. Whether you're planning a romantic escape or a family holiday, immerse yourself in the authentic charm and serene beauty of the Chianti countryside at this unparalleled haven.

Villa Benefizio

Villa Benefizio offers a charming, elegant, and exclusive retreat 3 km from Montepulciano's historic center. Guests can relax or work in six stylish rooms with modern facilities and panoramic views. The villa, built around an 18th-century Renaissance guard tower, features a restored structure integrated with modern furnishings. Products from the farm are used in the Villa’s restaurants. Wi-Fi and satellite TV are available in each room.

Sole del Chianti

Halfway between Florence and Siena, among the verdant hills and the vineyards of Tuscany, stands the resort “Sole del Chianti”, where the sound of nature prevails along with silence and privacy. Here it’s still possible to experience the country life of times gone by.

Villa Aggia

Countryside views, traditional architecture and modern luxury at Villa Aggia make for the quintessential Perugia holiday—with a contemporary twist. Spend a dreamy week or two with friends and family, reserve the property for a relaxed Italian honeymoon.

Villa Marcellina

Part of the Ville La Marcellina estate (20-acres estate), this villa is an expansive property with all modern amenities making it perfect for big group holidays.