Villas Province of Siena

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597 villas

Suite Il Tinaio. Villa Caprera, Siena Farmhouse.

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$161

Walk to Town! Luxury Villa in Montepulciano, Tuscany w/ Pool & Spa!!

Montepulciano villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 58 minutes

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Price per night from

$1,031

Morgana

Buonconvento villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

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$1,705

Beautiful cottage 2/9 people with pool, near Siena

Trequanda villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

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$222

Spacious Stone Villa in the Heart of Tuscany

Casciano villa

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 6

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$229

Podere Lucignano Secondo - Apt. La Mangiatoia (ground floor)

Nusenna villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$296

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$173

Romantic farm for 2/4 persons with pool near Siena

Trequanda villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$111

Ancient villa in Chianti with pool and wonderview

Castellina In Chianti villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$373

Villa with Pool and Jacuzzi private Deal 2024

Siena villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

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$124

Tuscany Villa with pool - Villa le Capanne holday in private villas

Siena villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

“Fantastic Hosts for this unique countryside Villa” Our trip to Italy still fresh in our minds so we wanted to write to tell others about our lovely experience at Villa le Capanne. We stayed with another couple for one week, make trips to Florence, Voltera, Pisa and more. Gina and Franco met us and welcomed us with enough goodies to keep us well taken care of until we could shop. Each day, a new treat appeared and they were all yummy-Gina is a fantastic baker and cook. The villa was spotless and just as described. Let me just say that the location is a bit of a challenge, but worth it for the views. Sitting around the pool and gazebo was very relaxing. You may need to allow extra time to get to the main roads for day trips but if you are prepared, it is not a problem. We had some great fun at the local restaurant, pizza on the weekend and then dinner on another night. The little village, Montecastelli Pisano was charming and we walked on a quiet street and found a violin maker who played us one of his own compositions-unique experience! Great hosts in a lovely setting!

Responds fast! avg. 2 hours 23 minutes

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$115

Villa LA VALIANA (Montepulciano)

Montepulciano villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Paradise in Tuscany!” This lovely villa has it all and is the kind of place that makes you want to stay and 'while away' the afternoon among its many outdoor spaces: whether it's dining in the gazebo overlooking the vineyard, watching as the evening sun sets over the gently rolling hills, relaxing in a chaise by the glistening pool, enjoying a café crème or glass of wine on the patio surrounded by roses, lemon trees and pots of flowers, or gazing beyond at Cortona high on a hill or Trasimeno Lake in the valley below, you will come to know this is a very special place. La Valiana is centrally located for explorations to nearby villages and wineries, Cortona, lovely Pienza (a favorite), Montepulciano or easy day trips to Montalcino, Orvieto, Siena, Arezzo, Florence, Chianti and beyond. It is comfortable and beautifully decorated in classic, Tuscan style with fine architectural details such as wrought iron arched windows, doors and Travertine marble floors. You will be well taken care of and looked after by Cecelia and her Family who are the most gracious hosts - they are dedicated to making your stay a wonderful, memorable one, making themselves available should you need any assistance. Their warm hospitality and attention to detail will make you feel special and, at once, a part of the family. If you opt to have a meal prepared and waiting for your arrival after a long day of travel or touring, it will not disappoint and, quite possibly, could be one of the best meals in all of Tuscany, especially when enjoyed under the stars. You will want for nothing - except perhaps to extend your stay, or at the very least, come back again! You can be sure we will be back!!

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Price per night from

$740

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

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$769

Cozy Collection of Villas in Tuscany

Montalcino villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 26

“Great stay- we hope to return!” We truly enjoyed our stay here. Matteo was a wonderful host and even met us outside of town to make sure that we did not get lost on the way to the agriturismo. The room was clean and very comfortable, especially important since we brought our 3 month old baby. The kitchenette was very useful and had everything we needed. This was a perfect place to stay while in town for Benvenuto Brunello because it allowed us a gorgeous drive and was away from crowds. We even enjoyed Quercecchio's wine, both Brunello and Rosso. Next time, we hope to visit around harvest time!

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Price per night from

$1,701

Casa Borgianni. Villa Caprera, Siena Farmhouse.

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“heavenly” A beautifully appointed home, with mercifully two batherooms, tastefully decorated with all that you need. The kitchen is a dream - everything you need. Lovely crockery, not bottom-of-the-range, and the bed linen also of excellent quality. Easy access to Siena, on the bus-route - useful to go into Siena by bus, because parking can be a nightmare in Siena itself. Lovely view of Siena, from the top floor. So all in all, this is a hard place to beat, if you want a few days, or longer, just to chill-out and relax and you would be forgiven for thinking Maggie Smith is going to come walking up the drive-way...

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$296

Private villa with pool in the Montalcino area. 8 persons in 5 bedrooms!

Castelnuovo dell'Abate villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

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$904

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$408

Villa Oliveto

Castelmuzio villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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$671

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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$1,233

Casa Baiocco // Private Tuscan Villa With Swimming Pool

Chiusi villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

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$141

Villa Cypress

Castelnuovo Berardenga villa

  • 9 bedrooms
  • 8 bathrooms
  • sleeps 12

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Price per night from

$1,660

Farm in Chianti

Castelnuovo Berardenga villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$771

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$183

Luxury Country Villa in Val d'Orcia, close to Montepulciano and Pienza

Chianciano Terme villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

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$456

Bargagli Penthouse

Pievescola villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$2,164

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$132

Podere Vitareto

Sinalunga villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$362

Villa La Bifora

Sinalunga villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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$777

Podere Monti, 7 bedrooms villa near Montepulciano. Private pool, A/C and Wi-Fi!

Sant'Albino villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 21

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$802

Villa la Strega

Siena villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 12

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$991

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

$610

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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$1,701

The Molinaccio 3

Montepulciano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$555

Giunia

San Lorenzo a Merse villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 27

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Price per night from

$2,735

Villa Belvedere

Poggibonsi villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$1,339

Charming Country Villa with Panoramic Private Pool

San Casciano dei Bagni villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$333

VILLA SUL LAGO - VILLA ON THE LAKE 9

Chiusi villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$207

La Dimora Main Villa + 1 Cottage for 18

Sarteano villa

  • 8 bedrooms
  • 1 bathroom
  • sleeps 18

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Price per night from

$3,153

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villas in Province of Siena

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