Luxury rentals in Montalcino

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Top-rated luxury vacation rentals in Montalcino

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Luxe

Villa in Montepulciano

Villa Montepulciano

Wine lovers will find much to appreciate at Villa Montepulciano. Located on an estate that still produces boutique wines and olive oils, the villa offers guests the chance to taste wines grown just outside. Six bedrooms, divided between a main house and guest cottage, offer space for up to fifteen guests, and rustic decor and panoramic views of the countryside are constant reminders you’re in the middle of Tuscany. A stay at Villa Montepulciano offers guests the chance to try local specialties from fruit to wine and olive oil. Sample produce from the orchard, enjoy a welcome basket of breakfast treats and taste wine with the villa’s owner, a sommelier. Create your own specialties on the outdoor barbecue, then, serve them on the outdoor dining table. Relax on the loungers around the pool or on the portico’s bench swing, and don’t forget to post vacation photos via the villa’s Wi-Fi. Built in the 1850s, the villa was recently restored in a way that respects its rustic past but provides modern comfort. In the living room, brick arches and terracotta floors nod to traditional Tuscan style, while a fireplace and contemporary sectional sofas create a welcoming place to sit. There’s room for everyone around the long dining table, situated in an airy space that’s open to the kitchen, where you’ll find modern appliances and both Italian- and American-style coffee makers. There are five bedrooms in the main house, and one bedroom in the guest cottage. Each has an en-suite bathroom and air conditioning, and is stocked with toiletries. In the main house, you’ll find three bedrooms with king beds, one bedroom with a queen bed and one bedroom with three twin beds. The guest cottage has a bedroom with a queen bed, as well as a sofa bed that can sleep three additional guests. As its name implies, Villa Montepulciano is just outside the town of Montepulciano. There’s a grocery store 7 minutes away by car, and restaurants, a tennis court, church and gym 10 minutes away in the center of town. It’s a 17.3 km drive to the Chiusi train station, a 27.4 km drive to the Bettolo golf course and a 41.8 km drive to the ski area at Mount Amiata. Take a day trip to the beach at Grosseto, 136 km away, and enjoy easy access to the Florence airport, also 136 km away. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Main House • Bedroom 1: King size bed, En-suite bathroom with tub and shower, Toiletries, Air conditioning • Bedroom 2: King size bed, En-suite bathroom with shower, Toiletries, Air conditioning • Bedroom 3 - Family Suite: Queen size bed (can be converted into 2 twins), Daybed, En-suite bathroom with shower, Toiletries, Air conditioning • Bedroom 4: Queen size bed, En-suite bathroom with shower, Toiletries, Air conditioning • Bedroom 5: Queen size bed, En-suite bathroom with shower, Toiletries, Air conditioning, Direct access to garden & pool Guest House • Bedroom 6: King size bed (can be converted to 2 twins), Twin size bed, Sofa bed, En-suite bathroom with shower, Toiletries, Air conditioning FEATURES & AMENITIES • More under “What this place offers” below OUTDOOR FEATURES • More under “What this place offers” below STAFF & SERVICES Included: • Complimentary mid week cleaning and towel change • Utility consumption up to 75 euros • Complimentary wine tasting • Complimentary vineyard tour • Welcome basket of breakfast items • More under “What this place offers” below At Extra Cost - advance notice may be required: • Meal plan • Horseback riding • Event fee • Cooking course • Weekday housekeeping • Additional cleaning service - 365 Euro • Utility consumption worth over 75 Euro • More under “Add-on services” below

Luxe

A serene swimming pool is surrounded by elegant lounge chairs with umbrellas, overlooking landscaped gardens and the charming stone villa. The clear water reflects the sky, while the villa's large glass doors offer stunning views of the outdoor space.

Villa in Monticiano

Mulino della Solaia

Muliono dello Solaia is a gorgeous Tuscan villa situated near the village of Iesa, south of Siena. Originally an olive oil mill, the structure has been restored and renovated into a fabulous vacation home, balancing exquisite contemporary comforts with vintage rustic artistry. Superb amenities include a swimming pool, alfresco dining and barbeque, and a gourmet kitchen. Five lovely bedroom suites with ensuite bathrooms accommodate families, destination wedding guests, and groups of friends up to ten in size. The historic home maintains much of its original character, with beautiful stone walls and facades, brick-lined thresholds, terracotta tile, and expertly landscaped gardens. The lower terrace features an ample swimming pool with elegant lounge chairs overlooking panoramic valley views. A covered patio extending from the house features a lovely outdoor sofa and dining table. Lush lawns surrounding the house offer a welcoming venue for special ceremonies or playful afternoons. Wide glass doors join the interior loggia to the terrace, forming an alfresco veranda in the summer months and a luminous, hearth-warmed habitat in winter. This space includes a comfortable lounge area with fireplace and sound system, flowing through a brick archway into a dining room furnished with timeless Tuscan elegance. The villa's kitchen features chef-grade appliances, a central table, and arched French doors to the patio. A small media room with table is located next to an antique millstone. The bedrooms balance fresh modern comforts with a dreamy, bucolic charm. There are three rooms with king beds, one with a queen, and one with a pair of twin beds. Each enjoys lovely views and light, and one of the king rooms opens directly to the garden. Air conditioning throughout the villa keeps you comfortable in the summer months. This secluded location in the Sienese hills gives a profound taste of the region's rich natural beauty and unique culture. There is a local food/convenience store about ten minutes away, and you're an easy drive from the Renaissance treasures of Siena. You're also an easy daytrip from the Grosetto region along the Tyrrhenian coast. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1: King size bed, Ensuite bathroom with stand-alone shower, Air conditioning • Bedroom 2: Queen size bed, Ensuite bathroom with stand-alone bathtub, Air conditioning • Bedroom 3: Twin size bed (can be converted to queen), Ensuite bathroom with stand-alone shower, Air conditioning • Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower, Air conditioning • Bedroom 5: King size bed, Ensuite bathroom with stand-alone shower, Air conditioning, Direct access to garden FEATURES & AMENITIES • More under “What this place offers” below OUTDOOR FEATURES • More under “What this place offers” below STAFF & SERVICES Included • Daily housekeeping (maximum 3 hours) • Change of linen and towels once a week • Concierge services • Complimentary welcome basket • Complimentary welcome dinner - Only for stays of 7 nights • More under “What this place offers” below Extra cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Luxe

Villa in Radicofani

5 out of 5 average rating, 11 reviews

Villa Poggio Fibbia

Steep yourself in Tuscan history, culture and cuisine at Villa Poggio Fibbia. This beautifully renovated farmhouse is just a half-mile from the fortress at Radicofani, in a medieval village that garnered mentions in both Dante’s Divine Comedy and Boccaccio’s Decameron. Today, this vacation rental features a lovingly curated mix of traditional and modern decor and five bedrooms—the perfect Val d’Orcia escape for groups of up to ten friends or family members. Look out over the hills of Tuscany or up to the fortress tower from outdoor living areas with an infinity pool, loungers and a barbecue. During the hottest parts of the day, retreat to the shade of the al-fresco sitting and dining areas; in the evenings, relax inside by the flat-screen TVs, Wi-Fi and fireplace. Though it still has the architectural charm of the region’s traditional homes, Villa Poggio Fibbia is a modern masterpiece inside. Its beamed ceilings and stone floors are juxtaposed with sleek furnishings in the living and dining rooms, as well as playful details like orange fabric or a trompe-l’oeil wall painting. The fully equipped kitchen is equally stylish and functional, too. This luxury property has two bedrooms with king beds, a primary bedroom with a double bed, and one bedroom with two twin beds. The fifth bedroom, ideal for families on holiday with children, has a French queen bed and a twin bed. All five bedrooms have private en-suite bathrooms. Spend your stay simply enjoying the villa or exploring the area. It’s well worth the climb to the Radicofani fortress for both the views and the history, not to mention the 15-minute walk to the nearest village, where you can stop for a drink in one of the bars or sit down to a honeymoon-worthy dinner in one of the restaurants. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: Double size bed, Walk-in closet, Ensuite bathroom with stand-alone shower with chromotherapy & bathtub with hand-held shower • Bedroom 2: French Queen bed, 1 twine size bed, Ensuite bathroom with stand-alone shower with chromotherapy • Bedroom 3: King size bed, Ensuite bathroom with combo shower/bathtub, Balcony • Bedroom 4: 2 Twin size bed (can be converted into a double bed), Ensuite bathroom with stand-alone shower with chromotherapy • Bedroom 5: King size bed, Ensuite bathroom with combo shower/bathtub FEATURES & AMENITIES • Alarm system OUTDOOR FEATURES • Lounge area STAFF & SERVICES Included: • One four course dinner or one cooking class included in the price. The specific day to be agreed • Linen change - every Saturday • Light housekeeping - every Wednesday (2 hrs per day) • Towel change - every Wednesday and Saturday • Air conditioning consumption • Heating consumption At Extra Cost – advance notice may be required: •Chef and cooking classes •Van with driver for airport transfer or any other need • Activities and excursions • Additional housekeeping (40 euros/hour) (Advance notice required)

Luxe

A welcoming entryway features a round wooden table at its center, surrounded by a decorative rug. Arched walls and large windows provide natural light, while elegant chandeliers hang from a textured ceiling. A cozy seating area is adorned with soft purple accents.

Villa in Sarteano

4.82 out of 5 average rating, 11 reviews

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

Luxe

A serene outdoor space features a clear swimming pool complemented by lounge chairs arranged around its edge. Natural stone walls and lush greenery provide a tranquil backdrop, while rustic buildings can be seen rising from the gently sloping terrain.

Villa in Chiusdino

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

Luxe

The outdoor area features a private swimming pool surrounded by wooden decking and sun loungers. Towering cypress trees are visible, along with a cozy gazebo. The farmhouse blends rustic architecture with modern amenities, set against a clear blue sky.

Villa in Radicofani

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

Luxe

The villa is positioned on a hillside, surrounded by expansive vineyards and olive groves. Rolling hills in the background contribute to a serene landscape, while the lush greenery creates a peaceful atmosphere. The estate features a large garden with trees and neatly arranged vineyard rows.

Villa in Cetona

5 out of 5 average rating, 23 reviews

Luxury Villa Justina Tuscany

Villa Justina is a hilltop sanctuary 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.

Luxe

The villa is set in a lush green landscape, featuring a spacious infinity pool surrounded by sun loungers. The building’s rustic architecture complements the natural surroundings, with expansive lawns and trees framing the view of the distant hills.

Home in Cinigiano

Il Poderone - Luxury Villa con piscina privata

Villa con piscina riscaldata, finemente ristrutturata situata in una tenuta privata di 700 ettari. Affittandola potrai vivere un'esperienza immersiva nei ritmi e nell'atmosfera suggestiva della maremma. Cureremo la tua permanenza in ogni dettaglio grazie al servizio di pulizia giornaliero delle stanze e ad un personal chef che ogni mattina preparerà la colazione/brunch. A tua disposizione anche percorsi di trekking sui laghi privati della tenuta e su richiesta massaggi e corsi di cucina.

Luxe

An aerial view captures the villa surrounded by lush greenery and vineyards. The hilltop town of Montepulciano is visible in the distance, framed by rolling hills and an expansive sky featuring scattered clouds. The landscape showcases a harmonious blend of nature and historical charm.

Villa in Montepulciano

5 out of 5 average rating, 7 reviews

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.