Province of Siena Rentals

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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

$1,033

Cottage in Chianti, with pool, spa, and wonderview

Castellina In Chianti cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$292

Ancient villa in Chianti with pool and wonderview

Castellina In Chianti villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$372

La Tinaia, Podere Patrignone - a Tuscan cottage with garden, views and pool

Castellina In Chianti cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“A Slice of Paradise” We stayed at Podere Patrignone for 5 days in September. It was wonderful to stay in a self contained apartment after 4 weeks of hotels in France. The farmhouse is charming, the apartments are unique and quaint, the countryside was picture perfect and the weather was unseasonably warm. Simon and Verity were such hospitable hosts, yet give the guests their own space. We thoroughly enjoyed the weekly meal Verity and Pam created for all the guests. You must have a car to truely experience all the hidden charms of Tuscany, and everything is so close and the quality of food and wine was impressive. Our favourite memory of staying at Podere Patrignone was sharing sunsets on the terrace with other guests and partaking of good wine, great conversation and so many laughs. We will be back for another slice of paradise.

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$185

Charming Apartment in Historic Center of Montepulciano, Tuscany

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$86

L'Olivo Gina, Minnie's Cottage: Your home in Tuscany, the land of Brunello

Montalcino house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$173

Tigli #1, two bedrooms apartment close to Montepulciano with Wi-Fi and pool!

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“family reunion” we looked for a place where the whole family could celebrate a 70'years birthday. We were altogether 4 families of 8 adults and 7 children. The property was ideal for us. We occupied 5 apartments and had the whole place at our disposal. It was nice that we had the whole property at our own so that we should not consider other residents. All apartments were in good standard and the pool area was nice. We had really no complains at all. One evening a pizza evening was arranged by the manager and it was splendid. Further the surrounding towns were interesting and marvelous.

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$194

Tigli #6, ground floor flat with one bedroom in Montepulciano area. Wi-Fi & pool

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$151

Apartment "The Hague" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$208

Tuscan countryhouse apartment in San Gimignano

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$105

Apartment "Belvedere" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$171

Tigli #2, apt Montepulciano area for 5 persons with A/C, Wi-Fi and swimming pool

Montepulciano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful place with beautiful vistas of the hills and valley fr” We were able to stay 5 days and 4 nights in this lovely place. The property was as or better than described. Very comfortable and clean. Everything we needed for the time we stayed there. It was a very nice location to be able to take day trips to Siena, Pienza, Montepulciano, Montalcino and Orvieto on the way back to Rome. Such great views from apt #2. We even saw deer in the evening and morning running through the fields below. Montepulciano is very close and you can be there in a matter of a few minutes to shop at the Conard or enjoy shopping and meals. There are a lot of rules on lists provided to follow regarding trash, cleaning, linens, etc. We didn't see much of the caretakers as they had other jobs/work, a new baby, etc. But they were very pleasant and helpful if we needed anything. This is definitely a place we would go back to again.Once we found it. I am glad we got to the location during the day and not at night. You just really have to believe the directions and keep going. The signs are a bit small and I am glad everyone was looking for them. Please go eat at the 13 Gobbi in Montefollonico about 5-6 miles away on a hill top to the north. You will love it. And have their house wine, great. By the way, a bottle of wine and olive oil was provided upon our stay. Both were very good. Wish I could have bought more of it.

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$194

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

$1,230

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Price per night from

$1,435

Tigli #5, flat near Montepulciano with 2 bedrooms. A/C, Wi-Fi and swimming pool

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Return visit” One again we enjoyed our visit to this well run set of apartments. They are ready on time, cleean and well equiped. A caretaker lives on site to provide backiup if needed. The gardena and pool are tell tended and maintained. Montipulciano is 10 mins away by car. Be aware that it is in the middle of the countryside with no shops or restaurants nearby.

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Price per night from

$172

Casa Baiocco // Private Tuscan Villa With Swimming Pool

Chiusi villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

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$141

"Policiano Suite" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$308

Apartment "Poggino" - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$185

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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Price per night from

$129

Studio "Rustic" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$128

Apartment "Pratino" - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$171

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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Price per night from

$800

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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Price per night from

$1,697

Studio "Borghetto" at The House of the Oaks - Montepulciano

Montepulciano studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$128

La Dimora Main Villa + 1 Cottage for 18

Sarteano villa

  • 8 bedrooms
  • 1 bathroom
  • sleeps 18

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Price per night from

$3,145

La Dimora Main Villa + 2 Cottages for 20

Sarteano villa

  • 9 bedrooms
  • 2 bathrooms
  • sleeps 20

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Price per night from

$3,505

Apartment rental in Tuscany

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 33 minutes

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Price per night from

$431

Tuscan apartment rental

Castellina In Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 3 hours 33 minutes

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Price per night from

$400

Vacation apartment in Tuscany

Castellina In Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 33 minutes

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Price per night from

$431

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

$2,372

La Dimora Main Villa for 14 adults plus 2 children

Sarteano villa

  • 7 bedrooms
  • 11 bathrooms
  • sleeps 16

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Price per night from

$2,777

Traditional Tuscan apartment

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 33 minutes

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Price per night from

$308

Chianti apartment rental

Castellina In Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 3 hours 33 minutes

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Price per night from

$271

Tuscan vacation apartment

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 33 minutes

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Price per night from

$431

Your Tuscan Home Away From Home

Sarteano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$120

Villa rental near Siena

Castellina In Chianti house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 3 hours 33 minutes

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Price per night from

$492

Spacious 2-bedroom, 2-bath apartment patio & pool

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$265

Viewing 38 of 310
rentals in Province of Siena

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