Piancastagnaio Rentals

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191 Houses

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

$1,032

Casale Santappiano

Barberino Val d'Elsa house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

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$556

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Price per night from

$383

Castello di Montalto - 3 Bedroom Villa in Chianti

Siena villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$409

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

San Gusme house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$364

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

$1,234

charming apartment in the village of Cetona

Cetona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$62

ART REBUS TOWER

Radda in Chianti tower

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$157

Villa Guarda Mare - Spectacular Pool with Sea View

Roccatederighi villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 55 minutes

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Price per night from

$501

contryhouse near siena: Apartment 2 Person

Sinalunga apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$457

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

$130

Farm in Chianti

Castelnuovo Berardenga villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$772

Luxury Country Villa in Val d'Orcia, close to Montepulciano and Pienza

Chianciano Terme villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

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$457

ART-HANGAR BY TUSCAN-EXPERIENCE

Montalcino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$716

The Castellare

Malafrasca - San Frustino villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$456

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

$611

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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Price per night from

$1,703

Villa Anita

Farneta house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 13

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Price per night from

$369

The Molinaccio 3

Montepulciano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$556

Home sweet home in medieval town!

Montefollonico apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 17 minutes

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Price per night from

$81

La Dimora Main Villa + 1 Cottage for 18

Sarteano villa

  • 8 bedrooms
  • 1 bathroom
  • sleeps 18

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Price per night from

$3,157

La Dimora Main Villa + 2 Cottages for 20

Sarteano villa

  • 9 bedrooms
  • 2 bathrooms
  • sleeps 20

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Price per night from

$3,518

Aiola

Sarteano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 12

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Price per night from

$1,663

Podere i Casini

Casole d'Elsa house

  • 12 bedrooms
  • 8 bathrooms
  • sleeps 26

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Price per night from

$2,044

The Molinaccio 7

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

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Price per night from

$1,111

Ferranesi, Tuscan Design Villa with private pool, perfect for small weddings

Chiusure villa

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 18

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Price per night from

$2,953

Il Sasso Il Sasso

Chianciano Terme house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

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Price per night from

$1,155

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

$2,381

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

$2,787

Romantica

Pienza villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 7 minutes

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Price per night from

$1,123

Il Fornacino

Rapolano Terme house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$273

Santantimo

Castellina In Chianti villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$496

Vallebuia

San Gimignano villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$1,234

Rustic home Il Torrione, private garden and pool

Radicondoli house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$177

Villa Vianci

Staggia villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

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Price per night from

$648

The Meleria

Monte San Savino townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$148

"Geranio". Delightful double bedroom with indipendent entrance in old farmhouse

Radicofani farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$124

The Hill

Ambra farmhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$970

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