Province of Siena Rentals

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82 Houses

Romantic Cottage in Tuscany

Radicofani cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 11 minutes

Match: Private outdoor pool (heated)

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Price per night from

$111

Villa with Pool and Jacuzzi private Deal 2024

Siena villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$124

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!!

Match: Private outdoor pool (heated)

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Price per night from

$741

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!

Match: Private outdoor pool (heated)

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Price per night from

$1,234

Casale Etruria

Chianciano Terme house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$353

Farm in Chianti

Castelnuovo Berardenga villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$771

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Price per night from

$911

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.

Match: Private outdoor pool (heated)

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Price per night from

$2,380

CASA FEBEA 6 people

Chiusi villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$210

Villa Sarteano

Contignano villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

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Price per night from

$1,947

Podere il Sogno

Tavernelle villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated)

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Price per night from

$908

Villa degli Olivi

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$826

TuscanFlat

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 7 minutes

Match: Private outdoor pool (heated)

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Price per night from

$173

Barn overlooking the vineyards

Gaiole in Chianti barn

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$161

la lodola

Crete Senesi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Private outdoor pool (heated)

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Price per night from

$148

VILLA TALCIONA

Poggibonsi apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated)

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Price per night from

$192

Responds fast! avg. 2 hours 58 minutes

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Price per night from

$1,763

Exclusive luxury villa in the Tuscan countryside. 14 rooms, pool, A/C and Wi-Fi!

Monticiano villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 28

Match: Private outdoor pool (heated)

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Price per night from

$3,603

Villa D'Orcia - Homelike Villas

Castiglione D'Orcia villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 15

Match: Private outdoor pool (heated)

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Price per night from

$633

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Price per night from

$911

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 20

Match: Private outdoor pool (heated)

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Price per night from

$346

Villa Molino

Montalcino villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (heated)

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Price per night from

$485

Villa for 19 ppl. with swimming-pool and garden at Monteroni d'Arbia

Monteroni d'Arbia villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 19

Responds fast! avg. 2 hours 50 minutes

Match: Private outdoor pool (heated)

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Price per night from

$3,605

Villa Parmolaia

Ville di Corsano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$1,939

Villa Radda

Selvole villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 7 minutes

Match: Private outdoor pool (heated)

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Price per night from

$2,943

Villa Radda - Villa with pool near Gaiole in Chianti

Gaiole in Chianti villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated)

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Price per night from

$763

Luxury Villa Pratomaggio

Radda in Chianti villa

  • 5 bedrooms
  • 9 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$2,764

Luxury Villa Faggeto

Siena villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 17

Match: Private outdoor pool (heated)

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Price per night from

$2,364

Villa Asciano 30 - Stunning villa with garden and pool in Val d'Orcia

San Giovanni d'Asso villa

  • 14 bedrooms
  • 15 bathrooms
  • sleeps 30

Match: Private outdoor pool (heated)

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Price per night from

$3,123

Luxury Villa in Radda,saltwater swimming pool,A/C,gym room,Turkish bath, sl 10

Radda in Chianti villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 58 minutes

Match: Private outdoor pool (heated)

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Price per night from

$2,666

Villa Benedetto - Modern villa with pool and sauna near San Gimignano

San Benedetto villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$690

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Price per night from

$1,298

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Price per night from

$2,042

Villa la Fonte - Homelike Villas

Casciano villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated)

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Price per night from

$1,740

Luxury Villa Castelio

Radda in Chianti villa

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated)

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Price per night from

$4,819

Villa Torre del Chianti

Radda in Chianti house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$2,294

Luxury Villa Lunablu

Cetona villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$1,940

Villa Montepulciano - Magnificent villa with garden and pool in Val d'Orcia area

Bivio di San Biagio villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

Match: Private outdoor pool (heated)

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Price per night from

$871

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rentals in Province of Siena

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