Luxury rentals in Montalcino

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

Villa Quercia by Burghesius

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

Beautiful modern villa with pool in Val D'Orcia

Nestled into the rolling hillside of Tuscany, this luxurious farmhouse enjoys sweeping views decorated with emerald lawns, lush gardens, and mature trees. With 17 beds, this spacious estate is perfect for large gatherings. Spend your days shooting pool, swimming, and playing tennis on the grass court. Inside, gorgeous architecture and high-end finishings await. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary:Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 2: Double size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 3: Double size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 4:  Double size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 5: 2 Twin size beds (can be converted to a double bed ) Ensuite bathroom with stand-alone shower • Bedroom 6: 2 Twin size beds (can be converted to a double bed , Ensuite bathroom with stand-alone shower • Bedroom 7: Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 8: Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 9: Double size bed, Ensuite bathroom with stand-alone shower FEATURES & AMENITIES • Home theater STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions

Tenuta Val D'Orcia

EXCLUSIVE VAL D’ORCIA Perched on a hilltop with breathtaking views over the Val d’Orcia, this extraordinary luxury villa—featured in the renowned interior design magazine AD (Architectural Digest)—is the perfect blend of tradition and modernity. Nestled in one of Tuscany’s most iconic areas, known for its rolling hills and postcard-perfect landscapes, the property offers an exclusive retreat for those seeking privacy, relaxation, and an authentic experience in a refined, one-of-a-kind setting.

Villa Montemaggio

This booking is a chance to stay in a real Tuscan Farmhouse that is situated inside an actual vineyard. Its a private property of the owners of the estate, completely refurbished to give every possible comfort but still live in the middle of nature. The setting is absolutely breathtaking amongst the rolling tuscan hills, far away from the noise of the concrete jungle and busy streets. Here the only noise you will hear is the chirping of the birds or faraway hum of the tractor in the fields.

Villa Eterna, Tuscan Haven in the Heart of Chianti

VILLA ETERNA - RADDA IN CHIANTI Only a five-minute walk from Radda in Chianti, the villa is set just outside the charming village. Surrounded by rolling vineyards, and postcard-perfect valleys, the villa offers spectacular views across the Florentine hills. Guests can walk to Radda for shops, restaurants, wine bars, and essential services, while the central Chianti location makes day trips to Florence, Siena, San Gimignano, Volterra, Montalcino, and other Tuscan highlights wonderfully easy.

Luxury Villa Tuscany

An exclusive estate set on 30 private acres of vineyards and olive groves—ideal for luxury travelers and families seeking serenity and style. The villa combines designer Italian furnishings, curated contemporary art, and timeless antiques. Recently transformed into a private residence, it offers five-star comfort with new premium bedding, linens, and kitchenware. Services are designed to meet the highest standards, including cleaning and options to add private cook or chef.

La Tuscia - Tenuta di Toscana, Boutique Villa

Casa La Tuscia is a beautifully restored 1700s farmhouse blending original “Pietra” and “Travi” with modern, luxurious interiors. This exclusive-use Luxe Villa is ideal for families, couples, friends, or small business groups. Set in the Tuscan countryside, it’s surrounded by its own vineyards and orchards. Guests enjoy an elegant experience with a serene spa, panoramic heated pool, jacuzzi in the olive grove, daily housekeeping, and high-speed Wi-Fi throughout the estate.

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.

Villa of Montesoli

Situated in a dominant position, Villa di Montesoli, overlooks Montalcino and Castiglion Del Bosco on one side and the Val d'Orcia on the other. Immersed among vineyards, olive threes and organic wheat fields, this Villa of new renovation offers maximum comforts in over 900 sqm. There are 9 bedrooms all with an ensuite bathroom, ideal for groups up to 18 people. Air Conditioning in every single room.

Luxury Retreat in the Tuscan Hills

A newly-restored Tuscan villa with stunning views across the Sienese hills. Set amid olive groves in the beautiful Val d’Orcia, the house has been restored to the highest specifications while maintaining its authentic Tuscan style and charm. The main house has 5 bedrooms sleeping 10 guests, and there is an adjacent annex which sleeps up to 4 guests in 2 bedrooms.

Villa Poggio Fibbia

Offered in the price with no extra cost daily served breakfast and two luxury Tuscan dinner or cooking class including food , service and wine. In stays less than seven nights , only one dinner or cooking class included Daily cleaning included Concierge service during the entire stay.