Province of Siena Rentals

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204 Houses

Beautiful Independent Tuscan Cottage For 2 With Spectacular Views

San Casciano dei Bagni cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Views amazing, house beautiful and Village so friendly” We stayed for one week at La Ginestra and could have been there for so much longer. We loved it, the view across the valley is a wow and the house is so tastefully decorated and of high quality. The village is just two minutes walk away and has a fab pub and lovely restaurants. I am a Food Technologist so food is very important to me - the butchers in the old town was fab, sausages and ham just so delicious. We really did feel accepted everyone was just so friendly to us. We toured most days and saw some beautiful Tuscan towns. We loved everything about it. Bed so comfy and beautiful, bedding crisp and white.

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$214

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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$1,031

Holiday home Il Corbezzolo with Infinity pool

San Gimignano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$612

Villa with Pool and Jacuzzi private Deal 2024

Siena villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

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$123

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$405

Tuscany Villas La Casetta del Borgo San Gimignano

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Perfect base to see all that Tuscany has to offer” La Casetta del Borgo was the perfect location for my recent trip to Tuscany with my wife. The unit is located in a resort with plenty of amenities including two pools and a very nice tennis court with faux grass that can be used for a small fee. It is a 10 minute drive to Montaione where one can go for dinner or buy groceries to cook in the unit's kitchen. All the necessary utensils are available to do some home cooking and I enjoyed a number of home cooked dinners and a delicious breakfast every morning thanks to my lovely wife. The main resort building has a restaurant that serves breakfast, lunch and dinner, however I didn't try it out so I can't say anything about it. Paolo, the owner, was a pleasure to deal with. I was having trouble finding the location with my GPS so Paolo had me meet him at his home which is just off the highway from Florence and very easy to find. To ensure that I found it with no problem Paolo drove to the resort while I followed . Once at the resort he had the keys, a nice bottle of wine, and plenty of info about the local area ready for me. Since he knew that I had the flu he even had some flu medication for me in case I needed it! The weather was unseasonably cold when we arrived and the bedding wasn't sufficient, but Paolo came to the rescue and drove over in the rain with more blankets for us. You'll be hard pressed to find a better host at this type of vacation rental. The location was perfect for us as it was very quiet, yet was within easy driving distance of many towns and cities in Tuscany. Smaller towns like Montaione and San Gimignon were within a 10-20 minute drive and Florence, Pisa, Lucca and Sienna were all within an hours scenic drive. If driving into Florence remember that free parking can be found at the Piazzale Michelangelo which is located outside of the ZTL and is a short walk to the Ponte Vecchio, Uffizi and other old city sites. The views are also magnificent! I wouldn't hesitate to recommend this property!

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$85

Casina di Arceno - Refurbished Farmhouse - sleeps 6 + 2 - pool - Chianti

San Gusme house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$361

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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$1,223

charming apartment in the village of Cetona

Cetona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$62

ART REBUS TOWER

Radda in Chianti tower

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$156

contryhouse near siena: Apartment 2 Person

Sinalunga apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$453

2 Bedroom Stone Cottage Rental in Chianti Countryside

Castellina In Chianti cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“A wonderful House in an wonderful area.” We want to say thankyou to Daniele for a wonderful week, we spend in Casanuova di Pietrafitta. The House is very lovely an nice equipped. The big terrace has a great view and is perfect for some relaxing moments. We will try as soon as possible to stay there again. Michael and Family from Munich

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$129

Farm in Chianti

Castelnuovo Berardenga villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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$765

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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$453

ART-HANGAR BY TUSCAN-EXPERIENCE

Montalcino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$710

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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$606

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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$1,688

The Molinaccio 3

Montepulciano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$551

Home sweet home in medieval town!

Montefollonico apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 17 minutes

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$80

La Dimora Main Villa + 1 Cottage for 18

Sarteano villa

  • 8 bedrooms
  • 1 bathroom
  • sleeps 18

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$3,128

La Dimora Main Villa + 2 Cottages for 20

Sarteano villa

  • 9 bedrooms
  • 2 bathrooms
  • sleeps 20

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$3,486

Aiola

Sarteano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 12

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$1,660

Podere i Casini

Casole d'Elsa house

  • 12 bedrooms
  • 8 bathrooms
  • sleeps 26

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$2,025

The Molinaccio 7

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

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$1,101

Ferranesi, Tuscan Design Villa with private pool, perfect for small weddings

Chiusure villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 18

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$2,926

Il Sasso Il Sasso

Chianciano Terme house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

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$1,144

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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$2,359

La Dimora Main Villa for 14 adults plus 2 children

Sarteano villa

  • 7 bedrooms
  • 11 bathrooms
  • sleeps 16

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$2,762

Romantica

Pienza villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 7 minutes

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$1,113

Il Fornacino

Rapolano Terme house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$271

Tuscan private villa with large pool and garden

Chiusi villa

  • 12 bedrooms
  • 6 bathrooms
  • sleeps 12

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$663

Santantimo

Castellina In Chianti villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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$492

Vallebuia

San Gimignano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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$1,223

Rustic home Il Torrione, private garden and pool

Radicondoli house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$175

Villa Vianci

Staggia villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

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$642

"Geranio". Delightful double bedroom with indipendent entrance in old farmhouse

Radicofani farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$123

Casa Felice is a 2 bedroom apartment in village of Gaiole, sleeps 6, shared pool

Gaiole in Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$107

Rustic apartment in ancient Tuscan village with 2 bedrooms and shaded terrace

Colle di Val d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$80

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rentals in Province of Siena

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