Province of Siena Rentals

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985 Houses

The Palazzetta Luca and Flavio Fanti

Castelnuovo dell'Abate apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$185

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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$1,033

Cesira Palazzina

Val d'Orcia b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$191

Holiday home Il Corbezzolo with Infinity pool

San Gimignano house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$616

Romantic farm for 2/4 persons with pool near Siena

Trequanda villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$111

Charming Apartment in Historic Center of Montepulciano, Tuscany

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$87

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

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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$738

Casa Bartoli at Borgo Mummialla-your Tuscan home !

San Gimignano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“A jewel in the heart of Tuscany.” Booking very easy helped by the owner. Apartment exceptionally comfortable with all the facilities we required. There was no problem moving in thanks to being met by Fabio when we arrived. A beautiful location with amazing views of Tuscany. An ideal spot for touring and visiting the many medieval towns in this area.

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$185

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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$1,697

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

Ciliegio house in Tuscany Chianti Hills

Castelnuovo Berardenga apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$99

Apartment Borgo Antico

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“superbe apartment at a suberbe place” We stayed at the lovely old town of San Gimignano a year ago. Everything was perfect. We received a warm welcome by a nice old lady. The apartment is just next to the central square in the pedestrian area. In summer you can even enjoy opera, theatre and music performances from one window of the apartment. Inside everything worked fine including a free washing machine. Payment and organisation worked smoothly, strongly reommended!

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$129

CHARME B&B * CAPANNA1826 * San Gimignano Tuscany

Ulignano b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 2

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$136

Casal d'Asso

San Giovanni d'Asso house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 7

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$797

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

San Gusme house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$363

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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$1,230

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$1,435

La Canonica

Colle di Val d'Elsa apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 5

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$351

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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$172

Noci bedsit house in Tuscany Chianti Hills

Castelnuovo Berardenga apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$62

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

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$308

House Giobatta A

Lucignano d'Arbia house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 56 minutes

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$247

Casale Montesoli

Buonconvento house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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$879

San Gimignano villa rental

San Gimignano house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 33 minutes

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$801

ART REBUS TOWER

Radda in Chianti tower

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$157

Quercia house in Tuscany Chianti Hills

Castelnuovo Berardenga apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$123

Suite Le Camelie

Caprera apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$148

Apartment "Poggino" - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$185

Casale Etruria

Chianciano Terme house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$352

Casale il Gualdo

Radda in Chianti house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

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$515

L'ANTICO GRANAIO

Montepulciano cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$153

Siena luxury villa rental

Asciano house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 33 minutes

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$862

Villa Fontanile C

Casole d'Elsa house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 56 minutes

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$249

Villa Cherubina

Staggia house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Responds fast! avg. 1 hour 56 minutes

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$814

Anticopozzo

Poggibonsi house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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$487

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

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