Vacation Rentals & Villas in Montepulciano

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791 Houses

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Boat available Pool or snooker table Staffed property Trampoline

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Price per night from

$86

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Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Boat available, Pool or snooker table, Trampoline

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Price per night from

$160

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$1,354

Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Boat available, Staffed property, Pool or snooker table, Trampoline

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Price per night from

$185

Grove House, villa with swimming pool

San Venanzo villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 24 minutes

3 of 4 match: Trampoline, Boat available, Pool or snooker table, Staffed property

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Price per night from

$283

2 MINI APPARTAMENTI ELEGANTI INDIPENDENTI CON PARCHEGGIO

San Martino in Colle house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Boat available, Trampoline, Pool or snooker table, Staffed property

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Price per night from

$80

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$308

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

2 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$308

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

2 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$136

CASALE DELLE LUCREZIE

Todi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Boat available, Trampoline, Pool or snooker table, Staffed property

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Price per night from

$99

Appartamento Bilocale con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Boat available, Trampoline, Pool or snooker table, Staffed property

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Price per night from

$121

Appartamento Trilocale A con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Boat available, Trampoline, Pool or snooker table, Staffed property

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Price per night from

$129

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$265

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

2 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$575

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$378

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$514

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

2 of 4 match: Boat available, Staffed property, Pool or snooker table, Trampoline

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Price per night from

$615

Villa Borgo Taverne

Corciano villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

2 of 4 match: Boat available, Staffed property, Pool or snooker table, Trampoline

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Price per night from

$702

Casale Aiaccia

Arezzo farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Boat available, Staffed property, Pool or snooker table, Trampoline

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Price per night from

$252

2 of 4 match: Boat available, Staffed property, Pool or snooker table, Trampoline

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Price per night from

$528

CARPE DIEM LIVING CLUB ASSISI.

Armenzano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Boat available, Trampoline, Pool or snooker table, Staffed property

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Cerbaia Rock Country Resort

Sovicille villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

2 of 4 match: Boat available, Trampoline, Pool or snooker table, Staffed property

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Price per night from

$1,106

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

Avigliano Umbro villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 4 match: Boat available, Trampoline, Pool or snooker table, Staffed property

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Price per night from

$676

Farmhouse in old mill in the Chianti hills

Monteriggioni house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 4 match: Boat available, Trampoline, Pool or snooker table, Staffed property

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Price per night from

$148

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 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$185

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

2 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$1,696

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

2 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$1,229

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

2 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$1,615

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

2 of 4 match: Boat available, Pool or snooker table, 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

2 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$492

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 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$610

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Boat available, Pool or snooker table, Staffed property, Trampoline

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Price per night from

$464

The Organic Farming

Terranuova Bracciolini farmhouse

  • 9 bedrooms
  • 18 bathrooms
  • sleeps 4

2 of 4 match: Staffed property, Trampoline, Boat available, Pool or snooker table

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Poggio Rosemary - luxury farmhouse

Montespertoli farmhouse

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 8

2 of 4 match: Boat available, Trampoline, Pool or snooker table, Staffed property

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Price per night from

$1,229

Villa Fada

Todi villa

  • 6 bedrooms
  • 9 bathrooms
  • sleeps 10

2 of 4 match: Boat available, Trampoline, Pool or snooker table, Staffed property

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Price per night from

$738

Villa Castellare de Sernigi stunning sunsets for 13/14 people

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

2 of 4 match: Boat available, Trampoline, Pool or snooker table, Staffed property

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Price per night from

$2,107

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