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Villas in Chianti

One of the most prestigous symbols of Chianti is that of a stately villa perched on the top of a panoramic hillside, surrounded by private gardens, olive groves and rows and rows of vineyards. The dream destination of Chianti is a beautifully restored villa which has been transformed into a romantic B&B, an elegant hotel with 5 star service or a full vacation rental. Choose to rent an entire villa for family, friends or even a destination wedding venue. Or if you are a smaller group, you will find many elegant villas have divided their accommodations into vacation apartments suitable for a couple, a small family or just a few friends making the tour of Tuscany.

Restored within the rigid Tuscan laws to maintain the rich culture of the area and the timeless beauty, these villas will amaze you with how they have withstood the test of time and still stand tall, graceful and most of all welcoming. Outfitted with modern amentities such as WiFi, outdoor swimming pools, wellness spas and air conditioning, your stay in a vacation villa rental in Chianti will be the highlight of your vacation.

The owners of the elegant homes have taken the time, not only to reconstruct a piece of their heritage, but to offer many extra services including daily housekeeping, on site wine tastings and cooking lessons, and sometimes even pizza parties and welcome buffets. Browse our selection of quality vacation villa rentals in Tuscany - you will be sure to find your perfect match.

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Cabbiavoli Villa -Luxurious Views and Villa

The elegant family home of Cabbiavoli Villa, set in the hills of Chianti just 30 km from Florence is the vacation spot for groups of up to 12 people.  The luxurious villa has 6 double rooms with en suite bathroom, a private pool, garden & terraces where you can enjoy the Tuscan countryside.

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Podere Villabassa: Paradise in Chianti

The Tuscany holiday accommodations located just minutes outside of Montespertoli promise typical Chianti vistas & a tranquil, spacious stay. You can’t help but appreciate the gardens, the decor, and the fabulous pool area.

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Villa Medicea di Lilliano: Luxury Country Residences near Florence

Check out our review of Villa Medicea di Lilliano with its splendid views, deluxe accommodations & attentive service. These holiday residences feature a relaxing, elegant environment minutes outside of Florence making it an ideal base for your vacation in Chianti.

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Villa Il Poggiale - A Favorite Wedding Destination

Villa il Poggiale is a beautiful Renaissance villa in the Chianti area near Florence. This charming bed & breakfast offers all the comforts and services of a luxury hotel in Tuscany, including a business center, wellness spa area and outdoor pool. A dreamy wedding venue!

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Villa I Leoni - Vacation in an Enchanted Landscape

Villa I Leoni is for large groups offering a swimming pool and withing walking distance of a small town.  The villa has 7 bedrooms and 3 double rooms and all the amenities necessary for a memorable holiday with family or friends.

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Villa Piaggia - Dream Vacation Villa

A vacation dream come true at Villa Piaggia: furnished with a modern decor and a fully-equipped kitchen, billiards room, dining room with fireplace, 9 bedrooms and swimming pool, this villa is perfect for a wedding or special event.

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Villa Vianci - Magnificent Villa & Spectacular Views

Villla Vianci is perched on the top of a prodominent hill near Monteriggioni. Perfect for up to 12 people, the villa is the ideal home away from home, and an elegant setting for a relaxing wedding.

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Villa Le Tortore in Siena

The private villa is perfect for 5 guests seeking the best of the Tuscan countryside while staying in the city of Siena. No need for a car, with a bus stop and supermarket a short distance from the villa, it will be the perfect base to enjoy all that Siena offers as well as day trips into Chianti to the north or to the Crete Senesi and Val d’Orcia to the south.

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