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

$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

$1,700

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agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Clothes dryer, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$308

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Clothes dryer, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$136

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Clothes dryer, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$87

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Clothes dryer, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$265

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Clothes dryer, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$1,619

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Clothes dryer, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$1,355

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 10 minutes

3 of 4 match: Swing set or jungle gym, Clothes dryer, Staffed property, Trampoline

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Price per night from

$308

Agriturismo Sertofano - apt K

Barberino Val d'Elsa apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

3 of 4 match: Trampoline, Clothes dryer, Staffed property, Swing set or jungle gym

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Price per night from

$185

Uva apartment, agriturismo Il Corniolo with garden and swimming pool

Corciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

3 of 4 match: Trampoline, Clothes dryer, Staffed property, Swing set or jungle gym

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Price per night from

$98

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Swing set or jungle gym, Clothes dryer, Staffed property, Trampoline

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Price per night from

$379

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Swing set or jungle gym, Clothes dryer, Staffed property, Trampoline

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Price per night from

$514

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Swing set or jungle gym, Clothes dryer, Staffed property, Trampoline

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Price per night from

$576

Cascina Toscana -Luxury Holiday House- Private Swimmingpool & Jacuzzi

Arezzo villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Clothes dryer, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$616

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Clothes dryer, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$161

Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Clothes dryer, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$185

Comfort under the Umbrian Sun! Pool and Air Conditioned!!

Spoleto villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Clothes dryer, Swing set or jungle gym, Trampoline

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Price per night from

$456

Holiday Villa in Cortona

Cortona villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

3 of 4 match: Staffed property, Clothes dryer, Swing set or jungle gym, Trampoline

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Price per night from

$690

Family Room

Castiglione del Lago apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Clothes dryer, Trampoline, Staffed property, Swing set or jungle gym

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Price per night from

$99

Santa Chiara - Pietramelina

Pierantonio apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Trampoline, Clothes dryer, Staffed property, Swing set or jungle gym

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Price per night from

$148

Farmhouse Il Palazzo dei Diavoli Montepulciano - Tuscany Val d 'Orcia

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Trampoline, Clothes dryer, Staffed property, Swing set or jungle gym

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Price per night from

$148

Walnut della Fonte

Radicondoli house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Trampoline, Clothes dryer, Staffed property, Swing set or jungle gym

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Price per night from

$173

Three Arches House

Chiusi apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Clothes dryer, Staffed property, Swing set or jungle gym

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Price per night from

$122

Girasole cottage, agriturismo Il Corniolo with garden and swimming pool

Corciano house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Clothes dryer, Staffed property, Swing set or jungle gym

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Price per night from

$67

Ghiande country house, agriturismo Il Corniolo with garden and swimming pool

Corciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Clothes dryer, Staffed property, Swing set or jungle gym

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Price per night from

$67

Agriturismo Podere Sertofano - apt J

Barberino Val d'Elsa farmhouse

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Clothes dryer, Staffed property, Swing set or jungle gym

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Price per night from

$154

Pulcianese in the countryside of the Tuscan hills but a stone's throw from Siena

Ville di Corsano farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Clothes dryer, Staffed property, Swing set or jungle gym

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Price per night from

$124

Il Palagione

Castellina In Chianti apartment

  • 5 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Clothes dryer, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$308

Farm House Erika Porcine

Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 12 minutes

2 of 4 match: Clothes dryer, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$111

Farm House Porcine Desire

Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 12 minutes

2 of 4 match: Clothes dryer, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$111

Casa San Carlo - apartment Orvieto

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Clothes dryer, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$148

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, Clothes dryer, Staffed property, Trampoline

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Price per night from

$739

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Swing set or jungle gym, Clothes dryer, Staffed property, Trampoline

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Price per night from

$465

Agriturismo Baciano - Appartamento Lepre

Capolona house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Clothes dryer, Trampoline, Staffed property, Swing set or jungle gym

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Price per night from

$72

Superior Apartment

Castiglione del Lago b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

2 of 4 match: Clothes dryer, Trampoline, Staffed property, Swing set or jungle gym

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Price per night from

$104

Agriturismo Villa di Giomici-the Tower

Valfabbrica house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Clothes dryer, Trampoline, Staffed property, Swing set or jungle gym

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Price per night from

$74

Viewing 38 of 1,201
rentals in Montepulciano

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