Luxury rentals in Montalcino

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

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)

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

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.

Tenuta I Terzi d'Ombrone-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.

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.

Villa Oliveto

Nestled in the heart of Tuscany, Villa Oliveto offers a luxurious escape with breathtaking views of the Val d'Orcia. The villa features three elegant apartments with kitchens and living rooms, 9 bedrooms, and 9 bathrooms, accommodating up to 18 guests. Outside, guests can relax in two panoramic pools and expansive gardens, perfect for al fresco dining. The 5,000 m² garden can host events for up to 80 people, combining comfort, privacy, and the timeless charm of Tuscany.

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.

Tuscany Farmhouse Estate | Vineyard Views & Pool

Welcome to Cuvée's Tuscan Farmhouse Estate, an iconic restored 16th-century farmhouse with quintessential Tuscan charm and modern amenities including an infinity pool, helipad, estate chickens, olive grove, and views of surrounding vineyards and Vertine Castle. Tucked in Chianti Classico's heart, experience designer elegance, restored architecture, and breathtaking Tuscan views. Walk to a Medieval castle, wake to farm-fresh eggs.

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.

Casalberna 14

Casalberna is nestled in the Unesco site of the Val d’Orcia area near the pretty and historic thermal spring town of San Casciano dei Bagni located in southern Tuscany. The property is 2km from the town and only a 15-20 minute walk, enjoyable ebike trip or a short drive.