Villas Castellina In Chianti

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Ancient villa in Chianti with pool and wonderview

Castellina In Chianti villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$373

Villa Patrignone - a beautiful large Tuscany Villa

Castellina In Chianti villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

“My favorite vacation experience” My first trip to Podere Patrignone was in 1999, and I've been back four times since my initial visit. The setting is incredible, and the views extend to miles and miles of Tuscany. It's amazing to sit on the terrace and see the towers of San Gimignano far in the distance. The villa is located just 3 kilometers from Castellina in Chianti, a charming village with unbelievable shopping for leather goods (Cappelletti), artwork, and other wonderful Tuscan items. Patrignone is a perfect location for day trips to Florence, Siena, Montalcino, and many other wonderful towns filled with incredible history. Back to the villa...Simon and Verity are carrying on the tradition of Simon's mom Carla, who renovated this beautiful villa that was originally a 14th century farmhouse. The main house has 7 rooms (each with its own bathroom...no sharing!), a great kitchen, and lots of space for lounging and relaxing. I've stayed in the main house as well as each of the 2-bedroom apartments...each with its own kitchen and living area. They all are wonderful, clean, charming, and have beautiful views. This year I participated in a cooking class conducted by Verity. Even after multiple cooking classes that I've taken throughout Italy, I can say that this was one of the best learning experiences: Verity is a fantastic teacher, cooking all the courses was great fun, and we got to dine and wine on our results. She cooked dinner for all of us on our first night, and everything was delicious! There were 18 of us on this trip, although I've been here with as few as one other person. I have lots of other friends who are encouraging a return trip. This year was in the last week of May, but I think we'll return for a visit in September next year. Carla and Simon and Verity have created a paradise that continues to call to me even after all these years and visits. Podere Patrignone is absolutely amazing and I can't wait to return!

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$610

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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$1,696

Sandonatino farmhouse

Castellina In Chianti villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$485

Santantimo

Castellina In Chianti villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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$496

Villa Beba

Castellina In Chianti villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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$405

CYPRESSES VILLA with private POOL

Castellina In Chianti villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$506

Villa Patrignone 7 bedroom Tuscany villa with pool

Castellina In Chianti villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$611

Villa Delle Upupe 8, Emma Villas

Castellina In Chianti villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$928

Casale Bellavista

Castellina In Chianti villa

  • 9 bedrooms
  • 11 bathrooms
  • sleeps 18

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$2,574

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Price per night from

$1,297

Great rentals within 20 miles that match your search

Vallebuia

San Gimignano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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$1,229

Palazzo - Tuscany

Montaione villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$1,416

Bargagli Penthouse

Pievescola villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$2,168

Tamara

Impruneta villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

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Price per night from

$1,331

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Tavarnelle Val di Pesa villa

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 20

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Price per night from

$1,898

Leonardo

Lucardo villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$932

Villa Cypress

Castelnuovo Berardenga villa

  • 9 bedrooms
  • 8 bathrooms
  • sleeps 12

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Price per night from

$1,664

Impruneta

Impruneta villa

  • 9 bedrooms
  • 8 bathrooms
  • sleeps 12

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Price per night from

$1,521

Adorna

Figline e Incisa Valdarno villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 20

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$4,891

VILLA PODERE MADONNA. Impruneta

Impruneta villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

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$345

Villa Il Palazzo, big garden, swimming pool, in Tuscany

Pergine Valdarno villa

  • 14 bedrooms
  • 11 bathrooms
  • sleeps 30

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$1,217

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$770

VILLA BETWEEN THE OLIVE TREES

Tavarnuzze villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$492

Castle in Chianti with private swimming pool, 15 minutes drive from Florence!

San Casciano in Val di Pesa villa

  • 11 bedrooms
  • 10 bathrooms
  • sleeps 15

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$1,369

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$407

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

Villa Belvedere

Gambassi Terme villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

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Price per night from

$589

La Tuia Vacanze

Montevarchi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$249

The Poacher

San Polo in Chianti villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 49 minutes

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$271

Il Capriolo sleeps 4 + 1 (on request)

San Polo in Chianti villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 49 minutes

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$246

Unique private villa near Tavarnelle. 11 bedrooms, pool, SPA, A/C in the Chianti

Tavarnelle Val di Pesa villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 20

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Price per night from

$1,688

Poggerina luxury private villa with stunning view

Greve in Chianti villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Beautiful location and villa, gracious and helpful hosts” I researched extensively before choosing this villa and it more than met our expectations. From the first email Emanuele and his family provided excellent service and were accessible and helpful. Moreover, they made us feel like more than paying guests, more like friends. The villa itself was very spacious and roomy, with a kitchen that had everything we needed. The views are spectacular, and it's quiet and peaceful. I would recommend doing both the pizza night and the cooking night. Both were excellent. Our stay couldn't have been any better. We would highly recommend this villa.

Responds fast! avg. 3 hours 16 minutes

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Price per night from

$615

Le Pratola Luxury Villa in Chianti with Heated Pool, top rated reviews.

Gaiole in Chianti villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 13

“Unforgettable Vacation!” My family and I (six of us) stayed at Le Pratola for a week in June. We had such a great time. The villa is beautiful and comfortable, and the views of the Tuscan hills are stunning. The team at Le Pratola is amazing. Laura, the cleaning lady, is a doll. The cooking class with Barbara is so much fun! Elena and Monica's (the personal chefs) meals are delicious. The villa is beautifully decorated and so comfortable. We all had the best vacation! We will definitely recommend the villa to family and friends. It was the best trip we've ever been on! We would like to thank the team at Le Pratola for making our vacation to Tuscany so special.

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Price per night from

$2,371

Villa il Castellaccio farmhouse chianti with pool

Greve in Chianti villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

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Price per night from

$553

Dreamy Tuscan Farmhouse near Florence, Podere la V

San Casciano in Val di Pesa villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Let's Go Back Soon!” The villa is beautiful, cheerful, and we felt at home. Ilaria keeps Podera very clean. Podera is fully equipped and updated. Ilaria and Rafael are the best hosts one can imagine, full of useful information about the area. They are very attentive. Ilaria showed us a 20 minute shortcut straight into a free parking lot in Florence! We did not have enough converters and Rafael went right out and bought some for us. They are both very accommodating and speak fluent English. I cannot say enough about these wonderful people. Their two boys, ages 4 and 6, are also charming and sweet. However, they are little boys and can be a bit noisy when playing, but Ilaria keeps them in line! The main town, San Casciano, is lovely and quaint and only a few minutes from the villa. There is plenty of history in the town. What we also loved, besides the terrific food, wine, the little outdoor market and the pasta shop with home made pastas, is in the evenings, families are out and about in the streets, enjoying a meal or espresso and meeting up with friends and neighbors. The children are with their parents having fun, no iPods! San Casciano felt like home. We had several dinners there and loved walking around. By the way, be sure to know the Italian for the days of the week or you may get a parking ticket ;) We planned on going back to Italy, south next time, but because Ilaria and Rafael are so great, and Podera La Villa so charming, we may decide to stay at Podere La Villa again, rather than somewhere else. It is in a perfect location to visit other towns. We went to Florence, Siena, Orvieto, Livorno, San Gimignano, Cirque Terra and Montapulciano! The only drawback was the wifi is wireless and is from the upstairs apartment, so we had to sit in the living room to get a signal. It was very hot. Wish we could have sat outside at one of several lovely seating areas.

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Price per night from

$316

Siena San Fabiano climatized villa with outdoor heated pool

Monteroni d'Arbia villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

“Perfect combo of charm, location & comfort in glorious Tuscany!” We first dicovered San Fabiano in summer 2003 and have made it a point to return with family and friends as often as we can ever since! The location is ideal for exploring Siena, all the hill towns of southern tuscany, the Chianti and even great for easy day trips to Florence. Besides the charm of this renovated farmhouse - it also has modenr comforts like ac, screened windows, kitchenettes in all the rooms and wireless internet - plus a swimming pool! We love walking into the little town of Monteroni for our morning cappucinos and hiking the trails around this lovely farm estate. Great for kids and family gatherings as well as couples. We get through New England winters by dreaming of returning to San Fabiano. Highly recommended!

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$1,229

Country House Nazzano in Chianti area near S.Gimignano (from 4 to 10 people)

Gambassi Terme villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fantastic Location” We spent a wonderful week in this property which was located centrally in the Tuscany Region. Two families were easily accommodated and we were able to link the connecting rooms as if we were in one large family home. Miriam and her husband were helpful, kind and gracious hosts and nothing was ever too much trouble. All the comforts of home and the peace and quiet of an idyllic getaway. We will return to the incredible property...if our friends and family don't beat us to it!

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Price per night from

$369

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villas in Castellina In Chianti

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