Vacation Rentals & Villas in Montepulciano

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3,328 Houses

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

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Il Poggio degli Olivi

Bettona apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared indoor pool, Stove, Staffed property

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$108

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

3 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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$307

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

3 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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$264

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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Price per night from

$574

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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$512

CASTEL BROKENAIRE groups in self-management

Perugia house

  • 10 bedrooms
  • 6 bathrooms
  • sleeps 26

3 of 4 match: Trampoline, Shared indoor pool, Stove, Staffed property

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$722

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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$737

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.

3 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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$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: Shared indoor pool, Stove, Staffed property, Trampoline

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Price per night from

$608

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

3 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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Price per night from

$1,695

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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$1,228

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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$1,614

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

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

3 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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$492

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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$1,354

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Shared indoor 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

2 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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$86

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

2 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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$135

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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$377

«Monastero San Silvestro-Historic Farmhouse

Cortona finca

  • 15 bedrooms
  • 10 bathrooms
  • sleeps 30

2 of 4 match: Stove, Trampoline, Shared indoor pool, Staffed property

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Price per night from

$2,395

Casale dei Pianetti

Sovana farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Shared indoor pool, Staffed property, Stove, Trampoline

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$185

Tipical rural cottage in Tuscany hills

Scansano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Shared indoor pool, Staffed property, Stove, Trampoline

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$74

Country house Il fornello APP. Hawthorn

Citta della Pieve farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

  • 13 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Shared indoor pool, Staffed property, Stove, Trampoline

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$123

Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Shared indoor pool, Staffed property, Stove, Trampoline

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$185

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Shared indoor pool, Staffed property, Stove, Trampoline

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$160

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Shared indoor pool, Stove, Staffed property, Trampoline

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$463

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.

2 of 4 match: Shared indoor pool, Staffed property, Stove, Trampoline

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Price per night from

$295

Il Palagione

Castellina In Chianti apartment

  • 5 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Shared indoor pool, Staffed property, Stove, Trampoline

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Price per night from

$307

Casa San Carlo - apartment Orvieto

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Shared indoor pool, Staffed property, Stove, Trampoline

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Price per night from

$148

Farm House Porcine Desire

Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 12 minutes

2 of 4 match: Shared indoor pool, Staffed property, Stove, Trampoline

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Price per night from

$111

Farm House Erika Porcine

Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 12 minutes

2 of 4 match: Shared indoor pool, Staffed property, Stove, Trampoline

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Price per night from

$111

Il piccolo ulivo

Siena townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Staffed property, Trampoline, Shared indoor pool, Stove

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Price per night from

$129

Crognole 6

Radda in Chianti villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Staffed property, Trampoline, Shared indoor pool, Stove

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Price per night from

$551

Villa a Panicale ID 3711

Panicale villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Staffed property, Trampoline, Shared indoor pool, Stove

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Price per night from

$435

Country House Lo Spigo 4

San Donato in Poggio villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Staffed property, Trampoline, Shared indoor pool, Stove

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Price per night from

$544

Viewing 38 of 3,328
rentals in Montepulciano

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