Vacation Rentals & Villas in Montepulciano

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3,380 Houses

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

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House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

  • 13 bedrooms
  • 1 bathroom
  • sleeps 5

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$123

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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$307

RELAIS CAMPIGLIONI

Montevarchi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$111

Casa San Carlo - apartment Città della Pieve

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$154

Casa San Carlo - apartment San Casciano

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$148

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$264

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$512

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

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the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$573

Apartment antico casale Maremma

Roccastrada farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$99

BUCCIA NERA bilo1

Arezzo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$184

apartment - GLICINE -

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$184

Holiday House Villa Patty

Apecchio guest house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 34 minutes

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$123

Casale Aiaccia

Arezzo farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$252

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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$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!

3 of 4 match: Children's pool, Stove, Staffed property, Trampoline

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$608

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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$1,693

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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$1,227

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

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$1,612

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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$736

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

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

3 of 4 match: Children's pool, Stove, Staffed property, Trampoline

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$491

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

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$1,350

Cypress

Montevarchi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$209

Tamarisk House -double in the green - house with 12 beds (3 suites 2 + 2)

Montecastrilli house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 12

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$490

Podere il Pino 6 - 2 bedroom apartment with terrace and shared swimming pool

Poggibonsi apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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$209

Family vacation accommodation in Umbria L'Alba at Alsagra, Umbria Italy

San Giovanni del Pantano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Children's pool, Stove, Staffed property

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$330

Casa Vecchia

Radicondoli farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Santa Chiara - Pietramelina

Pierantonio apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Trampoline, Children's pool, Stove, Staffed property

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$148

BUCCIA NERA bilo3

Arezzo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Children's pool, Stove, Staffed property

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$184

Southern Tuscany Experience: your home with view + pool. Choose your activities!

Magliano in Toscana townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

3 of 4 match: Trampoline, Children's pool, Stove, Staffed property

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$184

TINAIA in PALAIA

Anghiari farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 50 minutes

3 of 4 match: Trampoline, Children's pool, Stove, Staffed property

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$123

Newcastle upon sangiovanniinpoggio

Monteroni d'Arbia villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 8

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Podere il Pino 1 - Apartment with private garden and shared swimming pool

Poggibonsi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

3 of 4 match: Trampoline, Children's pool, Stove, Staffed property

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$172

3 of 4 match: Trampoline, Children's pool, Stove, Staffed property

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$191

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Children's pool, Stove, Staffed property, Trampoline

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Price per night from

$307

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$86

Viewing 38 of 3,380
rentals in Montepulciano

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