Province of Siena Rentals

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624 Houses

Chianti Luxury Suite, Boutique Rental, Radda in Chianti - Siena

Radda in Chianti cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Dreams do come true in Radda” We spent a month in Europe and Radda was the last leg of our journey and the absolute best part of our trip. Besides the breath taking vistas that abound in all directions, the accommodations are spectacular. A comfortable bed, a gorgeous bathroom and a quaint sitting area with sink and fridge. Evenings we would enjoy a glass of wine on the terrace overlooking the orchard. The gardens are filled with rows and rows of lavender. Exquisite! The entire villa is like a setting from a romantic movie about Italy. To be really decadent, we had a massage poolside that Mila arranged for us. It was heaven. It really is a place to find peace and tranquility, away from the noise of life. Mila is a charming hostess and a fountain of knowledge re the neighboring villages and history. She was fascinating to listen to and not the least bit intrusive. If we needed her she was there, otherwise she respected our privacy. My one wish would be, to have the opportunity to return again to this paradise. Thank you Mila for a wonderful experience in Chianti.

Match: Private pool

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Price per night from

$335

Monteriggioni Suite 4

Monteriggioni house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Private pool

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Price per night from

$231

Romantic Cottage in Tuscany

Radicofani cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 11 minutes

Match: Private pool

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Price per night from

$112

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

Tuscany Villa with pool - Villa le Capanne holday in private villas

Siena villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

“Fantastic Hosts for this unique countryside Villa” Our trip to Italy still fresh in our minds so we wanted to write to tell others about our lovely experience at Villa le Capanne. We stayed with another couple for one week, make trips to Florence, Voltera, Pisa and more. Gina and Franco met us and welcomed us with enough goodies to keep us well taken care of until we could shop. Each day, a new treat appeared and they were all yummy-Gina is a fantastic baker and cook. The villa was spotless and just as described. Let me just say that the location is a bit of a challenge, but worth it for the views. Sitting around the pool and gazebo was very relaxing. You may need to allow extra time to get to the main roads for day trips but if you are prepared, it is not a problem. We had some great fun at the local restaurant, pizza on the weekend and then dinner on another night. The little village, Montecastelli Pisano was charming and we walked on a quiet street and found a violin maker who played us one of his own compositions-unique experience! Great hosts in a lovely setting!

Responds fast! avg. 2 hours 23 minutes

Match: Private pool

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Price per night from

$116

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 pool

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Price per night from

$744

Tower Gates - luxury villa in Chianti!

Gaiole in Chianti villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Private pool

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Price per night from

$768

Private villa with pool in the Montalcino area. 8 persons in 5 bedrooms!

Castelnuovo dell'Abate villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$909

Podere Osteria

Pienza apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$310

Casal d'Asso

San Giovanni d'Asso house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 7

Match: Private pool

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Price per night from

$723

Villa Oliveto

Castelmuzio villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$675

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 pool

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Price per night from

$1,240

Match: Private pool

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Price per night from

$1,430

Casa Baiocco // Private Tuscan Villa With Swimming Pool

Chiusi villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$142

Casa Oliveto

Castelmuzio house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$708

Casale Stine

Monteroni d'Arbia house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Private pool

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Price per night from

$148

Casale Montesoli

Buonconvento house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$885

San Gimignano villa rental

San Gimignano house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Private pool

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Price per night from

$806

10 bedroom Siena villa rental

Ville di Corsano house

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 20

Match: Private pool

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Price per night from

$1,581

Belmonte House

Castellina In Chianti house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$374

Casale Etruria

Chianciano Terme house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$355

Casale il Gualdo

Radda in Chianti house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

Match: Private pool

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Price per night from

$519

montechiaro Shed

Siena house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$620

Siena luxury villa rental

Asciano house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

Match: Private pool

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Price per night from

$806

Farm in Chianti

Castelnuovo Berardenga villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$775

Villa Cherubina

Staggia house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

Responds fast! avg. 45 minutes

Match: Private pool

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Price per night from

$820

Anticopozzo

Poggibonsi house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$490

Match: Private pool

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Price per night from

$184

ART-HANGAR BY TUSCAN-EXPERIENCE

Montalcino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Private pool

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Price per night from

$719

Barn Cafaggiola

San Gimignano house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$299

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$133

The Angolino

Radda in Chianti house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$264

Romantic hideaway in the heart of Chianti

Radda in Chianti house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Private pool

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Price per night from

$150

Podere Vitareto

Sinalunga villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$364

Villa La Bifora

Sinalunga villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Private pool

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Price per night from

$781

Podere Monti, 7 bedrooms villa near Montepulciano. Private pool, A/C and Wi-Fi!

Sant'Albino villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 21

Match: Private pool

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Price per night from

$807

Casina Teo

Monteriggioni house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Private pool

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Price per night from

$222

Villa la Strega

Siena villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private pool

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Price per night from

$997

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rentals in Province of Siena

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