Private Estate Villa Castiglioni

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  • Stone buildings in a sunlit courtyard, with a potted tree and a hillside in the background under a blue sky.

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  • Yoga mats arranged around a willow tree on a grassy hill overlooking a vineyard.

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  • Bathroom with wooden vanity, rectangular sink, mirror, and window with a view.

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  • Living room with stone walls, white sofas, wooden coffee table, and colorful pillows.

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  • Bedroom with a large bed, artwork on the walls, and a wooden ceiling.

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  • Wine bottles displayed on shelves and a table inside a dimly lit archway.

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  • Swimming pool with lounge chairs, stone wall, wooden fence, and green hills under a blue sky.

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  • Outdoor table set for a meal with green chairs, blue tablecloth, and a view of rolling hills.

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  • Pool table in a room with a large window overlooking a green landscape. Cue sticks, and a round cabinet visible.

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  • Yoga mats and props arranged under a tree in a grassy outdoor setting.

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  • Brick pizza oven with tools, herbs, and prep area in a stone-walled outdoor kitchen.

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Set on a working wine estate, a country mile from the medieval hilltop town of Radda, this six-bedroom villa has sensational views of Chianti’s olive groves and vineyards – especially from the terrace of the tower at one end of the property as the sun sets. It’s ideal for families and friends travelling together, with several terraces for outdoor dining, including one overlooking the pool and children’s play area beyond. There’s plenty to keep all ages entertained, from billiards and foosball to pétanque, plus a yoga studio (on request) and hammam. 6 bedrooms, sleeps 12


When you book one of our Private Estates in Chianti, your stay comes with a host of additional experiences, services and treats, including:

• A case of Tuscan wine and a welcome hamper of specialty foods from local producers, from artisan cheesemakers to homemade breads and homegrown olives.
• Welcome and farewell dinners at the villa, prepared by a highly esteemed local chef.
• Wine-tasting at the villa or in the winery on your estate, with an expert from one of Chianti’s leading vineyards.
• A cookery class with a local Italian chef, who will tailor the class to suit your party’s taste and ability.
• A session with a professional photographer, who will come to the villa to capture some special moments, for the best set of holiday photos you’ve ever had.
• Exclusive goodie bags of gifts for children and adults.
• A dedicated local host who will take care of every detail of your stay, with daily visits and round-the-clock availability on WhatsApp, should you need them.
• Pre-arrival grocery shopping service.
• An airport meet-and-greet service to whisk you through the airport to your waiting private car.
• Private return airport transfers.
• A beautifully presented breakfast every day, at a time to suit you.
• Daily housekeeping.


If interested in a free quote for this property, please click below and fill out the form and on the Private Estate Rental box choose Private Estate Villa Castiglioni. Please note that you are requesting to see if this is property is available for a free quote and/or booking.

I want a free quote for this Private Estate

Private Estate Villa Tavernaccia

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  • Lush Italian garden with statues, trees, and distant mountains. Sunlight filters through the leaves, casting shadows on the green grass.

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  • Bedroom with a four-poster bed. Pink and white striped curtains frame the bed. A desk with lamps and artwork on the walls.

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  • Living room with red couches, coffee table, and arch windows overlooking a green landscape.

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  • Elegant bedroom with pale green walls, bed, wooden furniture, and patterned curtains.

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  • A sunlit room with blue armchair, wooden table and chair, a window and flowers.

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  • Tennis net and court with two racquets, tennis balls, and a yellow house in the background.

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  • An archway frames a sunset view of a valley. Orange light illuminates the arch and highlights the landscape.

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  • Staircase in a building entrance, white steps, wrought iron railing, baskets on stands, arched doorway.

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  • Outdoor dining table set for a meal, with a scenic hilltop view.

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  • Bright kitchen with white cabinets, two tables, fresh produce, and red tile floor.

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  • Poolside scene with a long rectangular pool reflecting trees and sky, three white-and-wood deck chairs on the grass with a view of rolling hills.

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Villa Tavernaccia is owned by an Italian sports agent who fell in love with the place long ago. It’s since been renovated by his sister, Rome-based Ilaria Miani, who mixed family antiques with swathes and stripes of color that reflect the local landscape. Comfortable sofas, black-and-white engravings, freshly cut flowers and open fireplaces in the dining and living/TV rooms enhance the effortlessly elegant feel.


The bedrooms are more theatrical and come with queen- or king-size beds, en suite shower rooms and air conditioning; the ground-floor double has a four-poster bed and another double is squirrelled away on a mezzanine beneath the tower. The six first-floor bedrooms include two twins, one double with a four-poster and two doubles with separate bathtubs and showers. All look onto the poetic grounds where white canvas chairs and loungers frame a 100-year-old swimming pool lined in pietra serena, mossy statues gaze over an antique amphitheater and a kitchen garden produces vegetables for cooking classes in the all-white kitchen with its marble worktops and antique cabinets.


WHY YOU’LL LOVE Villa Tavernaccia

  • Eight bedrooms, sleeps 16
  • Views of the rolling Tuscan hills at every turn
  • Refined interiors mixing polished antiques with theatrical stripes
  • Tower room for sunset aperitivos
  • Vast, beautiful grounds including woodland, ancient amphitheatre and kitchen garden
  • Tennis and clay bowls courts


When you book one of our Private Estates in Chianti, your stay comes with a host of additional experiences, services and treats, including:


• A case of Tuscan wine and a welcome hamper of specialty foods from local producers, from artisan cheesemakers to homemade breads and homegrown olives.

• Welcome and farewell dinners at the villa, prepared by a highly esteemed local chef.

• Wine-tasting at the villa or in the winery on your estate, with an expert from one of Chianti’s leading vineyards.

• A cookery class with a local Italian chef, who will tailor the class to suit your party’s taste and ability.

• A session with a professional photographer, who will come to the villa to capture some special moments, for the best set of holiday photos you’ve ever had.

• Exclusive goodie bags of gifts for children and adults.

• A dedicated local host who will take care of every detail of your stay, with daily visits and round-the-clock availability on WhatsApp, should you need them.

• Pre-arrival grocery shopping service.

• An airport meet-and-greet service to whisk you through the airport to your waiting private car.

• Private return airport transfers.

• A beautifully presented breakfast every day, at a time to suit you.

• Daily housekeeping.


If interested in a free quote for this property, please click below and fill out the form and for the Private Estate Rental box  choose Private Estate Villa Tavernaccia. Please note that you are requesting to see if this is property is available for a free quote and/or booking.

I want a free quote for this Private Estate

Private Estate Villa Pianvecchio

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  • Cozy outdoor seating area with stone wall. White sofa, wooden chair, ottoman, art, and arched doorway.

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  • Bathroom with wooden shelves, floating sink, and shower with glass door.

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  • Cozy living room with fireplace, bookshelves, dark sofa, and warm lighting.

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  • Stainless steel kitchen with large island, stove, and stone archway.

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  • Outdoor patio with metal furniture, overlooking a vineyard in Tuscany.

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Just 3km from the medieval town of Radda in Chianti, this sensitively restored five-bedroom Tuscan farmhouse sits on a family-owned wine estate. Perfect for multi-generational gatherings and groups of friends, it has masses of space, from the contemporary living areas to the children’s playground and outdoor pool with panoramic views of the olive groves and vineyards. There’s also a gym and steam room, and for alfresco dining, a pizza oven, barbecue and well-stocked wine cellar. The region is renowned for its pretty historic towns, plus it’s an hour’s drive to the blockbuster cities of Florence and Siena.


  • Five bedrooms, sleeps 10
  • Dreamy farmhouse on a working wine estate
  • Beautiful heated outdoor pool
  • Games for all ages and a children’s play area
  • Outdoor kitchen and loggia-shaded dining area
  • A gym and steam room
  • Well-stocked wine cellar
  • An hour’s drive to both Florence and Sien


When you book one of our Private Estates in Chianti, your stay comes with a host of additional experiences, services and treats, including:


• A case of Tuscan wine and a welcome hamper of specialty foods from local producers, from artisan cheesemakers to homemade breads and homegrown olives.

• Welcome and farewell dinners at the villa, prepared by a highly esteemed local chef.

• Wine-tasting at the villa or in the winery on your estate, with an expert from one of Chianti’s leading vineyards.

• A cookery class with a local Italian chef, who will tailor the class to suit your party’s taste and ability.

• A session with a professional photographer, who will come to the villa to capture some special moments, for the best set of holiday photos you’ve ever had.

• Exclusive goodie bags of gifts for children and adults.

• A dedicated local host who will take care of every detail of your stay, with daily visits and round-the-clock availability on WhatsApp, should you need them.

• Pre-arrival grocery shopping service.

• An airport meet-and-greet service to whisk you through the airport to your waiting private • car.

• Private return airport transfers.

• A beautifully presented breakfast every day, at a time to suit you.

• Daily housekeeping.


If interested in a free quote for this property, please click below and fill out the form and for the Private Estate Rental box  choose Private Estate Villa Pianvecchio. Please note that you are requesting to see if this is property is available for a free quote and/or booking.

I want a free quote for this Private Estate

Private Estate Villa Pianvecchio

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  • Indoor spa with a small pool, large windows, rustic ceiling, and a copper shower fixture.

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  • Modern white bathroom with shower, bidet, and floating double sink. Wooden window frames, black fixtures.

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  • Pool area with loungers, surrounded by green grass and olive trees under a bright sky.

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  • Bedroom interior with bed, exposed wood beams, stone walls, window, and mirror.

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  • Dining area with long table and chairs; colorful mural in the background, exposed wooden beams.

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  • Spa area with sauna, jacuzzi, and large arched window.

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  • Cozy living room with fireplace, dark blue sofa, and exposed beams. Wine rack on the right. Brick wall and stone flooring.

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With interiors of terracotta tiles and exposed beams and bold abstract art on the stone walls, Il Cellese fuses quintessential Tuscan charm with state-of-the-art modernity. Headline acts include the indoor and outdoor pools, an open-air yoga studio and indoor wellness area with gym and sauna. The estate’s nearby winery offers a private restaurant space that invites oenophiles to sample wine produced by the villa’s own vineyard, where custom barrels are painted by artists Santiago Ydáñez and Miki Leal. (Take home your favorite bottles in the villa’s custom-made crocodile leather trunk.) In the beautifully landscaped gardens is a wood-fired pizza oven and barbecue for those who love to cook, with a terrace for under-the-stars suppers overlooking Chianti’s hills and Il Cellese’s rows of vines. 10 bedrooms, sleeps 19


When you book this Private Estate in Chianti, your stay comes with a host of additional experiences, services and treats, including:


• A case of Tuscan wine and a welcome hamper of specialty foods from local producers, from artisan cheesemakers to homemade breads and homegrown olives.

• Welcome and farewell dinners at the villa, prepared by a highly esteemed local chef.

• Wine-tasting at the villa or in the winery on your estate, with an expert from one of Chianti’s leading vineyards.

• A cookery class with a local Italian chef, who will tailor the class to suit your party’s taste and ability.

• A session with a professional photographer, who will come to the villa to capture some special moments, for the best set of holiday photos you’ve ever had.

• Exclusive goodie bags of gifts for children and adults.

• A dedicated local host who will take care of every detail of your stay, with daily visits and round-the-clock availability on WhatsApp, should you need them.

• Pre-arrival grocery shopping service.

• An airport meet-and-greet service to whisk you through the airport to your waiting private car.

• Private return airport transfers.

• A beautifully presented breakfast every day, at a time to suit you.

• Daily housekeeping

If interested in a free quote for this property, please click below and fill out the form and for the Private Estate Rental box  choose Private Estate IlCellese. Please note that you are requesting to see if this is property is available for a free quote and/or booking.

I want a free quote for this Private Estate

Villa Il Santo

  • Stone building covered in green vines with red-trimmed windows and doors, set against a blue sky and rolling hills.

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  • Terrace with white sofas, overlooking rolling green hills and cloudy sky.

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  • Rolling green hills and forest under a cloudy blue sky.

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  • Patio with a pergola overlooking a rolling green landscape under a partly cloudy sky.

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  • Infinity pool with lounge chairs, umbrellas, overlooking Tuscan hills on a cloudy day.

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  • Outdoor dining table set for a meal overlooking a scenic hilltop view, with hanging globe lights.

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  • Two patterned chairs face a small table by an arched window with a scenic countryside view.

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  • Rustic kitchen interior framed by wooden doors; includes light fixture, stools, and countertop.

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  • Bathroom with a freestanding white tub, pedestal sink, and window; warm tones, indoor plant.

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This tranquil retreat is like a Tuscan hilltop village in miniature. The owners – a hotelier and an antiques dealer – have sensitively restored the traditional honey-hued sandstone buildings, retaining original features while giving the interiors a contemporary shake-up with Salone del Mobile statement pieces. Set high in a secluded spot between Florence and Siena, the location makes for utter privacy, peace, and spirit-lifting views across Tuscany’s vine-threaded hills from verandas, garden terraces, and a sensational infinity pool.


WHY YOU’LL LOVE Villa Il Santo

  • Eight bedrooms, sleeps 16.
  • A first-night chef-prepared feast of traditional Tuscan cooking, served along with a case of wine from a local vineyard.
  • The sensational hilltop setting with sunny, rose-scented terraces that looks out over the valley towards San Gimignano’s towers
  • Serious design credentials and top-quality furnishings
  • Outdoor kitchen and dining area complete with Fontana pizza oven
  • Dreamy hand-tiled infinity pool with day beds and parasols


Inclusions: When you book one of our Private Estates in Chianti, your stay comes with a host of additional experiences, services and treats, including:


• A case of Tuscan wine and a welcome hamper of specialty foods from local producers, from artisan cheesemakers to homemade breads and homegrown olives.

• Welcome and farewell dinners at the villa, prepared by a highly esteemed local chef.

• Wine-tasting at the villa or in the winery on your estate, with an expert from one of Chianti’s leading vineyards.

• A cookery class with a local Italian chef, who will tailor the class to suit your party’s taste and ability.

• A session with a professional photographer, who will come to the villa to capture some special moments, for the best set of holiday photos you’ve ever had.

• Exclusive goodie bags of gifts for children and adults.

• A dedicated local host who will take care of every detail of your stay, with daily visits and round-the-clock availability on WhatsApp, should you need them.

• Pre-arrival grocery shopping service.

• An airport meet-and-greet service to whisk you through the airport to your waiting private car.

• Private return airport transfers.

• A beautifully presented breakfast every day, at a time to suit you.

• Daily housekeeping.


If interested in a free quote for this property, please click below and fill out the form and for the Private Estate Rental box choose Private Estate Villa Il Santo. Please note that you are requesting to see if this is property is available for a free quote and/or booking.

I want a free quote for this Private Estate