Luxury rentals in Province of Siena

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Top-rated luxury holiday rentals in Province of Siena

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Luxe

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

$5,223 SGD per night

Luxe

Villa in Radicofani

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)

$2,194 SGD per night

Luxe

Villa in Montalcino

Villa La 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

$3,145 SGD per night