Vacation Rentals & Villas in Montepulciano

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735 Houses

Grove House, villa with swimming pool

San Venanzo villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 24 minutes

Match: Boat available Games room Staffed property

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Price per night from

$281

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Boat available Games room Staffed property

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Price per night from

$86

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Ripostena 9

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$1,221

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Staffed property, Boat available, Games room

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Price per night from

$159

Appartamento Bilocale con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$120

Appartamento Trilocale A con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$127

BUCCIA NERA bilo1

Arezzo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$184

CASALE DELLE LUCREZIE

Todi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$98

Agriturismo Incrociata Dispensa

Pietraviva farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$135

Agriturismo Incrociata Granaio

Pietraviva farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$135

Agriturismo Incrociata Greppia

Pietraviva farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$193

Ripostena 7-Trinciatoio

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Boat available, Games room, Staffed property

2 of 3 filters match

Price per night from

$1,221

Ripostena 6-the dryer

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Boat available, Games room, Staffed property

2 of 3 filters match

Price per night from

$1,221

Ripostena 11 the barn

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$1,221

2 Bedrooms Flat Crete Senesi

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$55

flat

Roccalbegna apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$86

Ripostena-5 The Remittance

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Boat available, Games room, Staffed property

2 of 3 filters match

Price per night from

$1,221

Ripostena 10

Casole d'Elsa townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$1,221

Agriturismo Poggio Del Pero

Lake Trasimeno farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$184

Tenuta i Lecci di Gurian Roberta - Il Cipresso

Terranuova Bracciolini farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$92

Le Stalle, Podere Patrignone

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$263

BUCCIA NERA bilo3

Arezzo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$184

CARPE DIEM LIVING CLUB ASSISI.

Armenzano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Boat available, Games room, Staffed property

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Beautiful home of 1400 in Umbria

Lake Trasimeno manor house

  • 6 bedrooms
  • 12 bathrooms
  • sleeps 12

2 of 3 match: Boat available, Games room, Staffed property

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Casale panoramicissimo con piscina S. Damiano

Todi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$110

Farmhouse "Le Case" with 3 apartments + double bedroom and extra bed

Gubbio house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 19 minutes

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$98

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

Avigliano Umbro villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$672

Ripostena-Melissa House 1

Casole d'Elsa house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$1,221

Antico Borgo Ripostena - 8 Casa Vecchia

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$1,221

The Granary, villa with pool and heated spa

San Venanzo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 24 minutes

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$232

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.

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$184

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!

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$605

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$1,685

Poggio Rosemary - luxury farmhouse

Montespertoli farmhouse

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 8

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$1,221

Casa Panorama Ad Est - Cooking class - Center of Italy

Perugia villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 18

Responds fast! avg. 50 minutes

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$55

Melia nest - Center Italy - Panorama Country

Perugia b&b

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$55

Villa Castellare de Sernigi stunning sunsets for 13/14 people

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

2 of 3 match: Boat available, Games room, Staffed property

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Price per night from

$2,093

Molinvecchio

Vallea villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

2 of 3 match: Boat available, Games room, Staffed property

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rentals in Montepulciano

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