Vacation Rentals & Villas in Montepulciano

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1,097 Houses

La Tinaia, Podere Patrignone - a Tuscan cottage with garden, views and pool

Castellina In Chianti cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“A Slice of Paradise” We stayed at Podere Patrignone for 5 days in September. It was wonderful to stay in a self contained apartment after 4 weeks of hotels in France. The farmhouse is charming, the apartments are unique and quaint, the countryside was picture perfect and the weather was unseasonably warm. Simon and Verity were such hospitable hosts, yet give the guests their own space. We thoroughly enjoyed the weekly meal Verity and Pam created for all the guests. You must have a car to truely experience all the hidden charms of Tuscany, and everything is so close and the quality of food and wine was impressive. Our favourite memory of staying at Podere Patrignone was sharing sunsets on the terrace with other guests and partaking of good wine, great conversation and so many laughs. We will be back for another slice of paradise.

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$185

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

$610

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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Price per night from

$1,697

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$86

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Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Games room, Table tennis, Trampoline

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$185

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$160

Ripostena 9

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$1,230

Fattoria Borgonuovo - Rosa

Cortona lodge

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Games room, Table tennis, Trampoline

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$122

Fattoria Borgonuovo - Geranio

Cortona lodge

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Games room, Table tennis, Trampoline

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$122

Fattoria Borgonuovo - Ortensia

Cortona lodge

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Games room, Table tennis, Trampoline

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$122

BUCCIA NERA bilo1

Arezzo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Games room, Table tennis, Staffed property

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$185

Appartamento Trilocale A con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$128

Appartamento Bilocale con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$121

Agriturismo Incrociata Dispensa

Pietraviva farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$136

Agriturismo Incrociata Granaio

Pietraviva farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$136

Ripostena-5 The Remittance

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Games room, Table tennis, Staffed property

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$1,230

Ripostena 7-Trinciatoio

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Games room, Table tennis, Staffed property

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$1,230

Ripostena 11 the barn

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$1,230

Ripostena 10

Casole d'Elsa townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$1,230

Agriturismo Incrociata Greppia

Pietraviva farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$195

Ripostena 6-the dryer

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Games room, Table tennis, Staffed property

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Price per night from

$1,232

Spacious 2-bedroom, 2-bath apartment patio & pool

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Games room, Table tennis, Staffed property, Trampoline

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Price per night from

$265

Poggerina luxury private villa with stunning view

Greve in Chianti villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Beautiful location and villa, gracious and helpful hosts” I researched extensively before choosing this villa and it more than met our expectations. From the first email Emanuele and his family provided excellent service and were accessible and helpful. Moreover, they made us feel like more than paying guests, more like friends. The villa itself was very spacious and roomy, with a kitchen that had everything we needed. The views are spectacular, and it's quiet and peaceful. I would recommend doing both the pizza night and the cooking night. Both were excellent. Our stay couldn't have been any better. We would highly recommend this villa.

Responds fast! avg. 3 hours 16 minutes

3 of 4 match: Staffed property, Games room, Table tennis, Trampoline

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Price per night from

$615

Siena Entire Tuscan Property 20P Private pool A/C Hottub wifi OutdoorKitchen

Sovicille villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 20

3 of 4 match: Staffed property, Games room, Table tennis, Trampoline

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Price per night from

$983

Tenuta i Lecci di Gurian Roberta - Il Cipresso

Terranuova Bracciolini farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Games room, Table tennis, Staffed property

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$93

Le Stalle, Podere Patrignone

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$265

BUCCIA NERA bilo3

Arezzo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Games room, Table tennis, Staffed property

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Price per night from

$185

CARPE DIEM LIVING CLUB ASSISI.

Armenzano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Games room, Table tennis, Staffed property

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Antico Borgo Ripostena - 8 Casa Vecchia

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Games room, Table tennis, Staffed property

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Price per night from

$1,230

Ripostena-Melissa House 1

Casole d'Elsa house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Games room, Table tennis, Staffed property

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Price per night from

$1,230

Villa Altura. Large pool, gym, billiard room. Staffed villa

Avigliano Umbro villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

3 of 4 match: Trampoline, Games room, Table tennis, Staffed property

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Price per night from

$677

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Games room, Table tennis, Staffed property, Trampoline

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Price per night from

$1,616

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Games room, Table tennis, Staffed property, Trampoline

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Price per night from

$738

Villa Brolio Quinto,exclusive use,secluded with large park and pool.

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

3 of 4 match: Games room, Table tennis, Staffed property, Trampoline

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Price per night from

$492

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Games room, Table tennis, Staffed property, Trampoline

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Price per night from

$1,353

Frate Sole, appartamenti in Borgo

Todi apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Staffed property, Trampoline, Games room, Table tennis

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Price per night from

$179

Casa Panorama Ad Est - Cooking class - Center of Italy

Perugia villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 18

Responds fast! avg. 50 minutes

3 of 4 match: Trampoline, Games room, Table tennis, Staffed property

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Price per night from

$56

Melia nest - Center Italy - Panorama Country

Perugia b&b

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

3 of 4 match: Trampoline, Games room, Table tennis, Staffed property

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Price per night from

$56

Viewing 38 of 1,097
rentals in Montepulciano

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