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Villas Province of Siena

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511 villas

Suite Il Tinaio. Villa Caprera, Siena Farmhouse.

Siena villa

1 bedroom / 1 bathroom / sleeps 4

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$133

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

Montepulciano villa

5 bedrooms / 6 bathrooms / sleeps 18

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$1,472

Morgana

Buonconvento villa

9 bedrooms / 9 bathrooms / sleeps 18

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$1,605

Beautiful cottage 2/9 people with pool, near Siena

Trequanda villa

2 bedrooms / 2 bathrooms / sleeps 9

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$127

Spacious Stone Villa in the Heart of Tuscany

Casciano villa

5 bedrooms / 2 bathrooms / sleeps 6

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$229

Design villa with pool and 360° spectacular Tuscan views near Siena

Asciano villa

11 bedrooms / 12 bathrooms / sleeps 21

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Price per night from

$2,406

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

Nusenna villa

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$225

One Bedroom Villa at Castello di Montalto in Chianti

Siena villa

1 bedroom / 1 bathroom / sleeps 2

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$169

Romantic farm for 2/4 persons with pool near Siena

Trequanda villa

1 bedroom / 1 bathroom / sleeps 4

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$85

Ancient villa in Chianti with pool and wonderview

Castellina In Chianti villa

3 bedrooms / 2 bathrooms / sleeps 6

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$326

Villa with Pool and Jacuzzi private Deal 2023

Siena villa

2 bedrooms / 3 bathrooms / sleeps 7

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$116

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. 1 hour 13 minutes

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$112

Hilltop Poolside 2 Bedroom Villa in Chianti

Gaiole in Chianti villa

2 bedrooms / 1 bathroom / sleeps 5

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$241

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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$602

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

7 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 1 hour 48 minutes

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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!

Responds fast! avg. 3 hours 17 minutes

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Price per night from

$1,660

Villas School

Pievescola villa

2 bedrooms / 3 bathrooms / sleeps 4

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Price per night from

$1,600

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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$205

Tuscany, Siena - Farmhouse I Pianelli

Murlo villa

2 bedrooms / 1 bathroom / sleeps 4

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$109

Podere Baiocco / LPRIVATE TUSCAN VILLA WITH SWIMMING POOL!!!

Chiusi villa

7 bedrooms / 8 bathrooms / sleeps 14

“Wow !!! :-)))” We have traveled to many fabulous places...but this villa is truly one of the finest! It is so beautiful and well kept. The owner Jacapo does everything possible to make your stay great! The 2 dinners he cook for us was wonderful! And his own labeled wine that he stocks right there for you...is great ! We had 10 the first week...celebrating with college girlfriend and spouses our 60th birthdays. The 2nd week we had family come and celebrated our 25th anniversary. More than my expectations were truly met! Nice modern bathrooms and good beds. We loved using the outdoor facilities Jacopo worked so hard to keep beautiful. Location was perfect for close day trips and then have this relaxing "home" waiting for us to chill down. I could go on and go! You will not be disappointed if you rent this home! I hope to return someday...but will forever have such wonderful memories! Peggy and Gary Henley/Dallas, TX

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$344

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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$882

New house

San Casciano dei Bagni villa

7 bedrooms / 6 bathrooms / sleeps 14

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Price per night from

$1,433

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$338

Villa Oliveto

Castelmuzio villa

5 bedrooms / 6 bathrooms / sleeps 10

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$655

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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Price per night from

$1,203

Casa Baiocco // Private Tuscan Villa With Swimming Pool

Chiusi villa

2 bedrooms / 4 bathrooms / sleeps 6

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$121

Villa La Ripa - Padronale

San Gimignano villa

2 bedrooms / 3 bathrooms / sleeps 4

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Price per night from

$181

Villa Cypress

Castelnuovo Berardenga villa

9 bedrooms / 8 bathrooms / sleeps 12

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$1,201

Vernaccia

San Gimignano villa

8 bedrooms / 7 bathrooms / sleeps 16

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Price per night from

$1,691

Quiet farmhouse

Pienza villa

6 bedrooms / 6 bathrooms / sleeps 12

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Price per night from

$845

Villa La Ripa - Barn

San Gimignano villa

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$241

Farm in Chianti

Castelnuovo Berardenga villa

6 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$527

Villa Le Crete, private house with 2 bedrooms. Pool and WiFi in the Val d'Orcia!

Castelmuzio villa

2 bedrooms / 2 bathrooms / sleeps 6

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$165

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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Price per night from

$337

Bargagli Penthouse

Pievescola villa

3 bedrooms / 4 bathrooms / sleeps 6

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Price per night from

$1,814

“What a great time!!” Poderi Val Verde was the perfect place to celebrate our 25th wedding anniversary. There was 3 couples sharing the Casa Pineta Villa which provided us with plenty of space. The villa was well equipped, very clean - we were pleasantly surprised that it did not have a musty smell being such an old villa and the property was beautiful. Poderi Val Verde is located central to most attractions -Florence, Sienna, Cortona - (1.5 hours travel time)- we would leave in the morning for a day trip and then returned to the villa to enjoy the well kept property - the pool was the perfect spot for gathering to chat about our adventures and enjoy a refreshing swim before dinner. Casa Pineta allows for entertaining both inside and outside the villa. The kitchen had all the essentails for us to prepare our meals that we enjoyed overlooking the grounds and the beautiful view of the mountains. From the villa, you can also hike into the village of Castellina. Castellina has shopping, grocery stores and great gelato. Ulrike offers a welcome dinner which was delicous. She prepares a homemade feast of Italian cuisine including appetizers, pasta, wild bore,dessert and her own wine. It was the perfect way to unwind after a long day of travel. Thank you for such a wonderful time and we hope to visit again!!!

Responds fast! avg. 1 hour 0 minutes

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Price per night from

$373

Responds fast! avg. 1 hour 13 minutes

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Price per night from

$121

Alfieri

Ponte a Bozzone villa

5 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$2,249

Viewing 38 of 511
villas in Province of Siena

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