Vacation Rentals & Villas in Montepulciano

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2,845 Houses

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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$740

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$87

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il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$379

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$576

Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$185

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$161

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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Price per night from

$309

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$309

#la Ghibellina2 Montalcino

Montalcino house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$74

The Lumachella

Porano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$99

Antica Canonica San Leolino

Panzano in Chianti apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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$204

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$465

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$265

Fattoria Quercia al Poggio - Apartment Proneta 1

Barberino Val d'Elsa apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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$219

#la Ghibellina Montalcino

Montalcino house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$124

B & B THE OLD Lieutenancy Suite Double

Citta della Pieve b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 13 minutes

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$99

the garden of the Etruscans

Chiusi villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 59 minutes

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Price per night from

$111

Meravigliosa villa con piscina e idromassaggio

Massa Martana villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$555

Casa Vacanze Biricocolo

Bucine apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$104

Appartamento signorile con soffitto a volte nel centro di Assisi

Assisi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$136

Ride the Beauty appartamento verde con la terrazza al centro di Assisi

Assisi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$160

Appartamento Rosso Giotto con vista al centro di Assisi

Assisi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$148

Casa NENA sulla strada del vino e dell'olio

Tavarnelle Val di Pesa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$56

Il Mulinetto Casa Vacanze

Canalicchio apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$87

Romantic Suite

Gubbio townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$173

Farmhouse La Pieve -Casale charming

Colle di Val d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$210

Red House Gubbio

Gubbio apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$173

La Casa di Smilla - (Bevagna)

Bevagna house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$87

Villa Chic X 2

Creti house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$272

Borgo Villa Certano - Roseto

Costalpino farmhouse

  • 1 bedroom
  • 4 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 10 minutes

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Price per night from

$105

Borgo Villa Certano - Tinaia

Costalpino farmhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 10 minutes

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Price per night from

$105

Ripostena 9

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$1,233

Borgo Villa Certano - Poggiolo

Costalpino farmhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 10 minutes

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Price per night from

$105

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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Price per night from

$185

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: Housekeeping Included, Microwave, Staffed property, Trampoline

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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

$1,701

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

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Price per night from

$1,356

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$1,233

Viewing 38 of 2,845
rentals in Montepulciano

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