Vacation Rentals & Villas in Montepulciano

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1,174 Houses

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Bicycles available Boat available Staffed property Trampoline

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Price per night from

$87

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Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Bicycles available, Boat available, Trampoline

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Price per night from

$161

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Boat available, Bicycles available, Staffed property, Trampoline

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Price per night from

$308

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Boat available, Bicycles available, Staffed property, Trampoline

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Price per night from

$136

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Boat available, Bicycles available, Staffed property, Trampoline

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Price per night from

$265

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Boat available, Bicycles available, Staffed property, Trampoline

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Price per night from

$379

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Boat available, Bicycles available, Staffed property, Trampoline

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Price per night from

$514

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Boat available, Bicycles available, Staffed property, Trampoline

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Price per night from

$576

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Boat available, Bicycles available, Staffed property, Trampoline

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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: Boat available, Bicycles available, Staffed property, Trampoline

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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: Boat available, Bicycles available, 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

3 of 4 match: Boat available, Bicycles available, Staffed property, Trampoline

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Price per night from

$1,701

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Boat available, Bicycles available, Staffed property, Trampoline

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Price per night from

$1,356

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Boat available, Bicycles available, Staffed property, Trampoline

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Price per night from

$1,620

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Boat available, Bicycles available, Staffed property, Trampoline

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Price per night from

$465

Three Arches House

Chiusi apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Bicycles available, Boat available, Staffed property

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Price per night from

$122

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

3 of 4 match: Boat available, Bicycles available, Staffed property, Trampoline

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Tipical rural cottage in Tuscany hills

Scansano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Staffed property, Boat available, Bicycles available, Trampoline

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Price per night from

$74

Country house Il fornello APP. Hawthorn

Citta della Pieve farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Staffed property, Boat available, Bicycles available, Trampoline

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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: Staffed property, Boat available, Bicycles available, Trampoline

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Price per night from

$124

Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Staffed property, Boat available, Bicycles available, Trampoline

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Price per night from

$185

Historical Palace Buonaccorsi 13^ century: 4 bedrooms San Gimignano View WiFi

San Gimignano guest house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

2 of 4 match: Boat available, Trampoline, Bicycles available, Staffed property

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Price per night from

$481

Ground floor apartment for 2 in Tuscan countryside

San Rocco a Pilli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Boat available, Trampoline, Bicycles available, Staffed property

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Price per night from

$173

Farm House Erika Porcine

Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 12 minutes

2 of 4 match: Staffed property, Boat available, Bicycles available, Trampoline

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Price per night from

$111

Farm House Porcine Desire

Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 12 minutes

2 of 4 match: Staffed property, Boat available, Bicycles available, Trampoline

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Price per night from

$111

Il Paluffo B&B Blue Room

Certaldo b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Staffed property, Boat available, Bicycles available, Trampoline

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Price per night from

$225

Casa San Carlo - apartment Orvieto

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Staffed property, Boat available, Bicycles available, Trampoline

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Price per night from

$148

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: Bicycles available, Boat available, Staffed property, Trampoline

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Price per night from

$308

Casa Azalea

Certaldo Alto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 4 match: Staffed property, Boat available, Trampoline, Bicycles available

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Price per night from

$144

Casa Dante

Certaldo apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 4 match: Staffed property, Boat available, Trampoline, Bicycles available

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Price per night from

$246

Casina

Certaldo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 4 match: Staffed property, Boat available, Trampoline, Bicycles available

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Price per night from

$102

Oliveta

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 4 match: Staffed property, Boat available, Trampoline, Bicycles available

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Price per night from

$154

Casa San Carlo - apartment Città della Pieve

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Staffed property, Boat available, Bicycles available, Trampoline

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Price per night from

$154

Casa San Carlo - apartment San Casciano

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Staffed property, Boat available, Bicycles available, Trampoline

2 of 4 filters match

Price per night from

$148

Villa Rosa dei Venti - Aliseo Cottage

Cortona cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Staffed property, Boat available, Bicycles available, Trampoline

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Price per night from

$284

Casa San Carlo - apartment Trasimeno

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Staffed property, Boat available, Bicycles available, Trampoline

2 of 4 filters match

Price per night from

$136

Casa San Carlo - apartment Bolsena

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

2 of 4 match: Staffed property, Boat available, Bicycles available, Trampoline

2 of 4 filters match

Price per night from

$124

Casa San Carlo - apartment Monteleone

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Staffed property, Boat available, Bicycles available, Trampoline

2 of 4 filters match

Price per night from

$111

Viewing 38 of 1,174
rentals in Montepulciano

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