Vacation Rentals & Villas in Montepulciano

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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

$614

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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Price per night from

$1,711

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

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Price per night from

$1,629

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$310

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Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Ceiling Fans, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$87

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Ceiling Fans, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$137

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Ceiling Fans, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$267

WINERY HOTEL in the Chianti Classico area "Apt PILU" ADULT ONLY +14

Greve in Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 2 hours 44 minutes

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Price per night from

$310

Casa San Carlo - apartment Bolsena

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

3 of 4 match: Staffed property, Ceiling Fans, Swing set or jungle gym, Trampoline

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Price per night from

$124

Casa San Carlo - apartment Monteleone

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Ceiling Fans, Swing set or jungle gym, Trampoline

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Price per night from

$112

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Ceiling Fans, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$1,364

San Carlo house

Monteleone d'Orvieto villa

  • 10 bedrooms
  • 7 bathrooms
  • sleeps 32

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Price per night from

$2,170

3 bedroom, 3 bathroom, spacious apartment with pool - sleeps 6 +1

Cortona house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$496

In Tuscany farm holidays

Radicondoli farmhouse

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

3 of 4 match: Trampoline, Ceiling Fans, Staffed property, Swing set or jungle gym

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Price per night from

$434

Borgo Rolling Hills Lodge

Castiglion Fiorentino apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 38 minutes

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Price per night from

$174

Villa Panconesi "Granaio"

Montespertoli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$96

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Swing set or jungle gym, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$744

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Swing set or jungle gym, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$1,240

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.

3 of 4 match: Swing set or jungle gym, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$186

Cascina Toscana -Luxury Holiday House- Private Swimmingpool & Jacuzzi

Arezzo villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$620

Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Ceiling Fans, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$186

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Ceiling Fans, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$162

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

3 of 4 match: Ceiling Fans, Staffed property, Swing set or jungle gym, Trampoline

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Family Room

Castiglione del Lago apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Swing set or jungle gym

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Price per night from

$100

Villa Mery

Gaglietole villa

  • 4 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Ceiling Fans, Staffed property, Swing set or jungle gym

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Price per night from

$149

Papaveri family holiday apartment in the heart of Italy

San Giovanni del Pantano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Ceiling Fans, Staffed property, Swing set or jungle gym

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Price per night from

$333

La Cascina Hotel Appartments

Marsciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Trampoline, Ceiling Fans, Staffed property, Swing set or jungle gym

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Price per night from

$88

Exclusive Villa in countryside 8pers., heatable pool, Umbria/Tuscany, historic

Citta della Pieve villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Trampoline, Ceiling Fans, Staffed property, Swing set or jungle gym

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Price per night from

$620

Villa Panconesi "Peasant"

Montespertoli apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Trampoline, Ceiling Fans, Staffed property, Swing set or jungle gym

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Price per night from

$128

Il Palagione

Castellina In Chianti apartment

  • 5 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$310

Farm House Erika Porcine

Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 12 minutes

2 of 4 match: Ceiling Fans, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$112

Farm House Porcine Desire

Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 12 minutes

2 of 4 match: Ceiling Fans, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$112

Casa San Carlo - apartment Orvieto

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Ceiling Fans, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$149

Agriturismo Baciano - Appartamento Lepre

Capolona house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$72

Il Poggio degli Olivi

Bettona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$110

Accommodation in chianti

Vagliagli apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Swing set or jungle gym

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Price per night from

$75

Agriturismo Il Drago App. La Tinaia

Bucine finca

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

2 of 4 match: Ceiling Fans, Trampoline, Staffed property, Swing set or jungle gym

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Price per night from

$131

Viewing 38 of 1,078
rentals in Montepulciano

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