Vacation Rentals & Villas in Montepulciano

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757 Houses

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Boat available Staffed property Trampoline Golf course on site or within 15 min walk

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Price per night from

$86

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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: Boat available, Golf course on site or within 15 min walk, Staffed property, Trampoline

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Price per night from

$307

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Golf course on site or within 15 min walk, Boat available, Trampoline

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Price per night from

$160

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Boat available, Golf course on site or within 15 min walk, Staffed property, Trampoline

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Price per night from

$1,228

Historic Villa Biribino (27 people) - Umbria

Citta di Castello b&b

  • 9 bedrooms
  • 21 bathrooms
  • sleeps 25

2 of 4 match: Boat available, Trampoline, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$1,329

Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Staffed property, Boat available, Golf course on site or within 15 min walk, Trampoline

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Price per night from

$185

Casale degli Olivi

San Giovanni del Pantano farmhouse

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

2 of 4 match: Staffed property, Boat available, Golf course on site or within 15 min walk, Trampoline

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Price per night from

$809

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, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$480

La Sosta di Braccio - casa vacanze

Macchie guest house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 4

2 of 4 match: Boat available, Trampoline, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$99

2 of 4 match: Staffed property, Boat available, Golf course on site or within 15 min walk, Trampoline

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Price per night from

$388

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, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$172

Historical Palace Buonaccorsi 13^ century : 8 bedrooms San Gimignano WiFi View

San Gimignano guest house

  • 10 bedrooms
  • 5 bathrooms
  • sleeps 20

2 of 4 match: Boat available, Trampoline, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$848

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Golf course on site or within 15 min walk, Boat available, Staffed property, Trampoline

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Price per night from

$307

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

2 of 4 match: Golf course on site or within 15 min walk, Boat available, Staffed property, Trampoline

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Price per night from

$135

Papaveri family holiday apartment in the heart of Italy

San Giovanni del Pantano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Boat available, Trampoline, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$329

Rogheta 4

Acquapendente finca

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Boat available, Trampoline, Golf course on site or within 15 min walk, Staffed property

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B x 3 -green holidays Lake Trasimeno Tuscany and Umbria B

Sant'Arcangelo farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Boat available, Trampoline, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$74

R x 3-Farmhouse in tiny village Tuscany Trasimeno Lake

Sant'Arcangelo farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Boat available, Trampoline, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$56

La Bottega _holiday house

La Bruna apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 2 hours 44 minutes

2 of 4 match: Boat available, Trampoline, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$74

Pulcianese in the countryside of the Tuscan hills but a stone's throw from Siena

Ville di Corsano farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Boat available, Trampoline, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$123

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 4 match: Golf course on site or within 15 min walk, Boat available, Staffed property, Trampoline

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Price per night from

$377

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Golf course on site or within 15 min walk, Boat available, Staffed property, Trampoline

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La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

2 of 4 match: Golf course on site or within 15 min walk, Boat available, 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

2 of 4 match: Golf course on site or within 15 min walk, Boat available, Staffed property, Trampoline

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Price per night from

$264

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Golf course on site or within 15 min walk, Boat available, Staffed property, Trampoline

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Price per night from

$512

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 4 match: Golf course on site or within 15 min walk, Boat available, Staffed property, Trampoline

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Price per night from

$575

La Cascina Hotel Appartments

Marsciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Boat available, Trampoline, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$88

Borgo Colognola-Dimora Storica

Cenerente apartment

  • 15 bedrooms
  • 17 bathrooms
  • sleeps 50

2 of 4 match: Boat available, Trampoline, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$9,824

Lecceto Casino

Volte Basse house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 4 match: Staffed property, Boat available, Trampoline, Golf course on site or within 15 min walk

1 of 4 filters match

Price per night from

$262

Villa Mery

Gaglietole villa

  • 4 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Boat available, Trampoline, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$148

Podere Molinaccio a 19th century stone farmhouse with private pool and park

Panicale farmhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 4 match: Boat available, Trampoline, Golf course on site or within 15 min walk, Staffed property

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Price per night from

$227

Brunello, the wine lover villa with pool - a Fontanaro Property

Perugia apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

2 of 4 match: Staffed property, Trampoline, Golf course on site or within 15 min walk, Boat available

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Price per night from

$553

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

2 of 4 match: Golf course on site or within 15 min walk, Boat available, Staffed property, Trampoline

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Price per night from

$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.

2 of 4 match: Golf course on site or within 15 min walk, Boat available, Staffed property, Trampoline

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Price per night from

$185

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

2 of 4 match: Golf course on site or within 15 min walk, Boat available, Staffed property, Trampoline

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Price per night from

$1,614

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

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

2 of 4 match: Golf course on site or within 15 min walk, Boat available, Staffed property, Trampoline

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Price per night from

$492

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

2 of 4 match: Golf course on site or within 15 min walk, Boat available, Staffed property, Trampoline

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Price per night from

$1,354

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!

2 of 4 match: Golf course on site or within 15 min walk, Boat available, Staffed property, Trampoline

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Price per night from

$609

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