Castiglione D'Orcia Rentals

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460 Houses

Montebello Montebello

Castiglione D'Orcia house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$491

Farm holidays Val d'Orcia

Castiglione D'Orcia b&b

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 5

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Price per night from

$370

Great rentals within 20 miles that match your search

Le Palazze, country b&b

Citta della Pieve b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 30 minutes

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Price per night from

$185

Villa Maria 3 piani (indipendente - garage)

Sinalunga house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$111

Rigomagno House for rent La Paterna

Sinalunga house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$87

Appartamento Lavanda Villa Pennella

Monticchiello apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$200

Villa Pennella

Monticchiello house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$398

Casa Gaia Luciano Giachi and Teresa chilly

Castiglione del Lago apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$62

Colombi Palace Montepulciano

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$145

La Macina Modì

Cetona house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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$81

B&b l'incanto

Montalcino b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$83

Borgo Terrosi B & B nestled in the green Val di Chiana

Santarello b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$85

MAGNOLIAHOUSEINTUSCANY Your '700 Tuscan villa with pool in exclusive use

Cetona villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$678

Poggio alla Rocca: the best location for Maremma guides

Grosseto hotel apartment

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 19

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Price per night from

$2,219

Poggio alla Rocca - ALBA

Casale di Pari studio

  • Studio
  • 1 bathroom
  • sleeps 2

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Price per night from

$247

Poggio alla Rocca - GINESTRA

Casale di Pari apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$370

Poggio alla Rocca - CORBEZZOLO

Casale di Pari apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$370

Poggio alla Rocca - SUGHERA

Casale di Pari apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$617

Pangea Villa 8 - Heated pool when open

Seggiano villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$986

Agriturismo collomici, camera fior d'aliso

San Casciano dei Bagni private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$105

Farm collomici ... sunflower, holidays and relaxation

San Casciano dei Bagni apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$111

Farm collomici ... poppy, holidays and relaxation.

San Casciano dei Bagni apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$117

The Palazzetta Luca and Flavio Fanti

Castelnuovo dell'Abate apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$185

Superb villa with pool 30 minutes from Siena and Montalcino

Montalcino villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$629

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

Holiday Resort in Montelpuciano B,air conditioning,swimmingpool,wine tasting

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 58 minutes

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Price per night from

$167

Lovely home of Olimpia in Montepulciano, wifi, wine and bikes, music and termal

Montepulciano apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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$124

Villa in Tuscany near Montepulciano and Vald'Orcia

Chianciano Terme b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$623

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

Apartment "Pratino" - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

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

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$308

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

$129

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

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$209

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

$1,233

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

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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Price per night from

$194

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

$173

Apartment Box Lucignano

Lucignano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$93

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