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Top-rated vacation rentals in Province of Siena

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Villa sa 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 sa Radicofani

5.0 sa 5 na average na rating, 11 review

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 sa Montalcino

Villa Palazzetta

Wake up early to catch the morning sun as it hits the mist in Val d’Orcia, turning the entire valley gold. You’ll have quite the view from this 5-acre hilltop villa 7-minute’s walk from Montalcino’s center. When the mist settles, set out to explore the property’s private vineyard and olive grove. Then, walk into town for breakfast. And, make sure to pick up some Brunello di Montalcino for later. Lovingly-restored, this 1600’s farmhouse has been updated with a state of the kitchen, in-floor heating and cooling, and the highest-end electronics and appliances. Staying true to its roots, Villa La Palazetta also boasts a private cantina and wine cellar, wood-burning pizza oven, and rustic fire pit. Dine outside amongst the mountain views. After dinner, issue a challenge on the night-lit bocce court. Make that home-cooked meal extra-special and get the concierge to book an in-house Italian cooking lesson. The professional kitchen is the perfect place to learn how to hand-make pasta and combine fresh local produce. When the party inevitably moves to the terrace, cool off in the swimming pool, or sample the finest local wines around the alfresco dining set. Rather dine out? Walk into Montalcino and wander within their historic city walls, where high-quality restaurants, bakeries, and gelato shops line the streets. Take a day trip to Siena and explore the museums, galleries, and churches of the ancient Renaissance city. And, wine tours of the World-famous Brunelle Vineyards are a great way to see all the different areas and landscapes of Val d’Orcia. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary : King size bed, Ensuite bathroom with stand-alone rain shower and bathtub, Safe • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower • Bedroom 3: 2 Twin size beds, Ensuite bathroom with stand-alone rain shower, Safe • Bedroom 4: Double size bed, Ensuite bathroom with stand-alone rain shower, Safe OUTDOOR FEATURES • Pergola STAFF & SERVICES Included • Firewood for outside pizza oven • Welcome gift • More under “What this place offers” below Extra cost (advance notice may be required): • Activities and excursions • Wine tasting • Babysitting • Cooking classes • More under “Add-on services” below

Villa sa Sarteano

5.0 sa 5 na average na rating, 5 review

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 sa Gaiole

5.0 sa 5 na average na rating, 6 review

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

Tuluyan sa 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 sa Montepulciano

5.0 sa 5 na average na rating, 6 review

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 sa Volterra

5.0 sa 5 na average na rating, 4 review

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 sa San Gimignano

5.0 sa 5 na average na rating, 3 review

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 sa Radicondoli

5.0 sa 5 na average na rating, 5 review

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.