Luxury rentals in Province of Siena

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Top-rated vacation rentals in Province of Siena

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Villa in Buonconvento

Castello di San Bartolomeo

Rising out a verdant Tuscan valley, this delightful and historic castle is set in the idyllic green surroundings of the Val d'Orcia. Fully renovated, the exterior stone turns golden at sunset, with guests free to enjoy the grand rooms, gardens, vineyard, courtyard and poolside lawns. A profusion of charming villages, vineyards and nature reserves are just minutes away, with majestic Siena nearby. Visible from kilometres away, the heights of Castello di San Bartolomeo announce themselves upon the guest from a distance. Entering the welcoming and Italian-tiled foyer, guests will experience a perfect night’s sleep in the huge bedrooms that feature vaulted ceilings and canopy beds. When morning dawns, guests can take in the stunning, rolling hillsides of the protected valley from the villa’s open-air terrace, before exploring the rambling, beautifully maintained gardens, the blue pearl that is the villa’s pool, or the perfectly-maintained tennis court. The stone, ivy-lined walls of the impressive inner courtyard make for a perfect oasis of peace, with the afternoon warmth emanating around the shaded alfresco table. This villa is surrounded by a wealth of day-trip options. Guests can taste the riches of the vineyard and visit the impressive wine cellars that buttress the castle, or venture a few minutes away to the charming medieval streets of the village of Buonconvento. To the east, the forest paths and impressive viewpoints of two nature reserves make for excellent hiking and family outing options. The Renaissance-splendor of Siena is on full display less than 30 minutes to the north, with the town’s stunning central square and UNESCO-protected architecture providing a jaw-dropping example of Italy’s rich history. After a day spent exploring the riches of the countryside, return to the huge interior dining space of the castle to savor a hearty Italian meal, before taking a rich glass of Sangiovese on the moonlit terrace. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with shower/bathtub combo, Dual vanity, Bidet, Air conditioning, Desk, Fireplace, Private balcony, Garden view • Bedroom 2: Queen size bed, Shared access to hallway bathroom, Shower/bathtub combo, Bidet, Air conditioning, Fireplace • Bedroom 3: Queen size bed, Ensuite bathroom with shower/bathtub combo, Bidet, Air conditioning, Desk, Fireplace • Bedroom 4: 2 Twin size beds (can be converted to a king), Ensuite bathroom with shower/bathtub combo, Bidet, Air conditioning, Fireplace Sophia Suite • Bedroom 5: Queen size bed, Ensuite bathroom with shower/bathtub combo, Bidet, Air conditioning, Office space, Crib, Fireplace Tower Suite • Bedroom 6: 2 Twin size beds, Ensuite bathroom with shower/bathtub combo, Bidet, Air conditioning, Lounge area, Television, Fireplace Family Suite • Bedroom 7: King size bed, Shared access to bathroom with Bedroom 8, Shower/bathtub combo, Bidet, Air conditioning, Fireplace • Bedroom 8: 2 Twin size beds (can be converted to a king), Shared access to bathroom in Bedroom 7, Shower/bathtub combo, Bidet, Air conditioning, Desk, Fireplace OUTDOOR FEATURES • Foosball table • Trampoline • More under “What this place offers” below STAFF & SERVICES Included: • Linen change - on Tuesday and Saturday Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Villa in Radicofani

5.0 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: • 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: • Activities and excursions • Additional housekeeping (40 euros/hour) (Advance notice required)

Villa in Radda in Chianti

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 in Sarteano

5.0 out of 5 average rating, 5 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

Villa in Gaiole

5.0 out of 5 average rating, 6 reviews

Villa Rietine

Villa Rietine embodies Tuscan serenity amid a lush landscape of olive, oak, and vineyards. With wide views of the Chianti hills around Lecchi and Gaiole, the lower and upper terraces welcome sunny pool plunges and meals in the aromatic breeze. Modern interiors emphasize rustic origins, with an eat-in kitchen, fireplaces in the salon and dining room, and arched doors to the veranda. Radda and Siena are an easy drive away. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1: Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 2: Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 3: Double size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 4: 2 Twin size bed (can be converted to a double bed), Ensuite bathroom with stand-alone shower FEATURES & AMENITIES • More under “What this place offers” below Extra cost (advance notice may be required): • Activities and excursions • Heating consumption • Tourist tax : 1,50 Euro per person, per night for the first 7 nights • More under “Add-on services” below

Home in Cetona

Luxury Villa Justina Tuscany

This unique place has a style all its own. Villa Justina is set on a hill top overlooking 27 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 in Montepulciano

5.0 out of 5 average rating, 6 reviews

Villa Benefizio

History is in the walls—and outside the windows—of this hilltop villa just outside Montepulciano. Parts of a 14th-century guard tower still show through the 17th-century building, and original beams light the ceilings. But the private wellness center has a modern feel, with indoor and outdoor pools and hydromassage. Walk around the grounds or into town, or visit an eco park dotted with sculptures. Copyright © Luxury Retreats. All rights reserved.

Villa in Volterra

5.0 out of 5 average rating, 4 reviews

Villa Finesterra

Preserving the historical character of the structure through an innovative approach: the design of Villa Volterra has been curated with the intention of creating the right balance between rustic and modern, tradition and design. The beating heart of the property is the living area, which is adorned by a panoramic glass wall with a spectacular view of the swimming pool that creates a seamless bridge to the garden.

Villa in San Gimignano

5.0 out of 5 average rating, 3 reviews

Villa Sarah

Villa Sarah enjoys spectacular views of the famous towers of San Gimignano. A large garden surrounds the entire structure and also the four-sided infinity pool with spa whirlpool, made with valuable stone of Cardoso, renowned local stone. Next to the swimming pool is a big dependance with large panoramic terrace, equipped outdoor kitchen, bbq, bar area, relaxation area and a large table to enjoy outdoor dining.

Villa in Radicondoli

5.0 out of 5 average rating, 5 reviews

Villa Mugnello

Villa Mugnello situata appena fuori le mura del paese medievale di Radicondoli è il luogo ideale per vivere il tuo soggiorno nella Toscana più autentica e incontaminata. Grandi famiglie o gruppi di amici possono trascorrere a Mugnello vacanze all'insegne del relax per vivere momenti di autentica gioia, benessere e bellezza.