Villas San Polo in Chianti

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407 villas

The Poacher

San Polo in Chianti villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 49 minutes

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Price per night from

$272

La Volpe 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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$247

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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Price per night from

$247

Great rentals within 20 miles that match your search

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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Price per night from

$1,375

Villa in Chianti with heated swimming pool and A/C

Certaldo villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 19

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Price per night from

$578

Appartamento in villa con piscina

Lastra a Signa villa

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$298

Leila

Trespiano villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

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Price per night from

$3,148

Tamara

Impruneta villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

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Price per night from

$1,330

Ippolita

Florence villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$947

Medea

Florence villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$1,330

Simonetta

Calenzano villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$667

Giorgina

Florence villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$858

Leonardo

Lucardo villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$932

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Tavarnelle Val di Pesa villa

  • 10 bedrooms
  • 9 bathrooms
  • sleeps 20

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Price per night from

$1,897

Impruneta

Impruneta villa

  • 9 bedrooms
  • 8 bathrooms
  • sleeps 12

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Price per night from

$1,520

Adorna

Figline e Incisa Valdarno villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 20

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Price per night from

$4,888

VILLA in Chianti Rufina with private pool

Londa villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 7 minutes

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Price per night from

$654

VILLA PODERE MADONNA. Impruneta

Impruneta villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$346

Country villa with pool and wonderful view

Loro Ciuffenna villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$543

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

Pergine Valdarno villa

  • 14 bedrooms
  • 11 bathrooms
  • sleeps 30

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Price per night from

$1,222

Panoramic villa with pool just a few kilometers from Florence

Vicchio villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$109

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

The Villa di Caiano

Londa villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$105

VILLA BETWEEN THE OLIVE TREES

Tavarnuzze villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

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Price per night from

$494

Villa bruschetti

Empoli villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 15

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Price per night from

$679

La Tuia Vacanze

Montevarchi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$250

Pietra E Mattoni Nel Cuore Del Chianti

Loro Ciuffenna villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$741

Tuscan villa overlooking 20 minutes from florence

Capraia e Limite villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$309

Romantic Tuscan Barn just 20 minutes from Florence

Capraia e Limite villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$136

Villa Le Terrazze in Florence, views, pool, no car needed

Florence villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

“It was the perfect place for us. Clean, roomy, easy to get to F” The Villa is beautiful! Lorenzo was a great host and he helped arrange transportation from the airport. We had taken a late train from Rome and got to the villa felt in the evening feeling very tired. Lorenzo was great the villa was awesome and we felt at home immediately. There were eight of us and there was plenty of room to spread out. Pros Beautiful Villa Very Clean Incredible View Wonderful Gardens Plenty of Room Full Kitchen with utensils Easy to Get to Florence (bus stop within walking distance) Cafe and small market within walking distance Lorenzo was great Cons Cannot think of any The location of the villa was perfect for our group. It is out of the hustle and bustle of the city but close enough to get into the city quickly. It only takes about 15 minutes to get to Florence by bus (which was easy to use, clean, and never too crowded.) By our bus stop there are a small market and cafe. So we could get espresso while waiting for our bus. One night we decided to eat in and the kitchen was equipped with all the utensils to make a full dinner. The Villa just added to the magic we were having on our trip and we would highly recommend it.

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Price per night from

$1,457

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

$617

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

$2,381

Villa il Castellaccio farmhouse chianti with pool

Greve in Chianti villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

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$556

Private house for 4 persons near Montelupo Fiorentino with pool and Jacuzzi!

Montelupo Fiorentino villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$232

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

$318

romantic ancient tuscan villa B&B near Firenze

Barberino Val d'Elsa villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$988

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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Price per night from

$611

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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Price per night from

$1,703

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villas in San Polo in Chianti

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