Vacation Rentals & Villas in Montepulciano

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2,676 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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$186

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

$611

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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$1,703

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

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Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$87

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Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$186

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$161

Beautiful 2-bedroom apartment villa in the heart of Chianti, pool & sunset views

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Ideal Tuscany accomodation” We spent five glorious days at Patrignone. We loved the location, perfect for visiting many of the small towns, and also Florence and Siena. Our 2 bedroom villa was beautiful, and everything we could have wanted. We especially enjoyed the wonderful hospitality of Simon and Verity, and their three sons. It made the holiday extra special. We will definitely be back.

3 of 4 match: Staffed property, Climbing frame, Microwave, Trampoline

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$297

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$389

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$309

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

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$309

Farmhouse Apartments with Pool in Quiet Rural Location - Rancale

Pierantonio apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$129

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$266

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

Spoleto villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$457

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

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Price per night from

$617

Villa Borgo Taverne

Corciano villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

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$705

Holiday House Villa Patty

Apecchio guest house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 34 minutes

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$124

San Carlo house

Monteleone d'Orvieto villa

  • 10 bedrooms
  • 7 bathrooms
  • sleeps 32

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$2,160

1 Bedroom, 1 bathroom apartment with Pool - sleeps 2 + 2

Cortona farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$210

In Tuscany farm holidays

Radicondoli farmhouse

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

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$432

Farmhouse Apartments with Pool in Quiet Rural Setting - Pietramelina

Pierantonio apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$84

Santa Chiara - Pietramelina

Pierantonio apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$148

Walnut della Fonte

Radicondoli house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$173

Casa San Carlo - apartment Orvieto

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$148

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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$1,234

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

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$1,622

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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$741

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

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

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$494

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

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$1,358

Casa San Carlo - apartment Città della Pieve

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$155

Casa San Carlo - apartment San Casciano

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$148

Casa San Carlo - apartment Trasimeno

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$136

Casa San Carlo - apartment Bolsena

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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$124

Casa San Carlo - apartment Monteleone

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$111

Casa San Carlo - Studio apartment Giulia

Monteleone d'Orvieto studio

  • Studio
  • 1 bathroom
  • sleeps 4

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Price per night from

$111

Molinvecchio

Vallea villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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Papaveri family holiday apartment in the heart of Italy

San Giovanni del Pantano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$331

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Price per night from

$3,085

Viewing 38 of 2,676
rentals in Montepulciano

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