Vacation Rentals & Villas in Montepulciano

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2,181 Houses

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Boat available Staffed property Trampoline Walking trips

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Price per night from

$87

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Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Boat available, Walking trips, Staffed property, Trampoline

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Price per night from

$136

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Walking trips, Boat available, Trampoline

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Price per night from

$160

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Boat available, Walking trips, Staffed property, Trampoline

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Price per night from

$265

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Boat available, Walking trips, Staffed property, Trampoline

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il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Boat available, Walking trips, 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, Walking trips, 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, Walking trips, Staffed property, Trampoline

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Price per night from

$576

La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

3 of 4 match: Boat available, Walking trips, 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, Walking trips, Staffed property, Trampoline

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Price per night from

$185

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Boat available, Walking trips, Staffed property, Trampoline

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Price per night from

$740

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Boat available, Walking trips, Staffed property, Trampoline

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Price per night from

$465

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, Walking trips, 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, Walking trips, Staffed property, Trampoline

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Price per night from

$1,701

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

3 of 4 match: Boat available, Walking trips, Staffed property, Trampoline

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Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Boat available, Walking trips, 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, Walking trips, Staffed property, Trampoline

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Price per night from

$1,620

2 of 4 match: Boat available, Trampoline, Walking trips, Staffed property

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Price per night from

$160

Hotel Rosati

Chiusi b&b

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 3

Responds fast! avg. 3 hours 59 minutes

2 of 4 match: Boat available, Trampoline, Walking trips, Staffed property

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Price per night from

$111

Soarzio apartment with pool near San Gimignano 4

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Boat available, Trampoline, Walking trips, Staffed property

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Price per night from

$124

Ancient house for two in Maremma

Sovana townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Staffed property, Boat available, Walking trips, Trampoline

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Price per night from

$74

Three Arches House

Chiusi apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Walking trips, Boat available, Staffed property

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Price per night from

$122

In Tuscany farm holidays

Radicondoli farmhouse

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

3 of 4 match: Trampoline, Walking trips, Boat available, Staffed property

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Price per night from

$432

casale herd

Fabro farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 4 match: Boat available, Trampoline, Walking trips, Staffed property

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Ancient Casolare Antico Cottage

Ficulle apartment

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 16

2 of 4 match: Boat available, Trampoline, Walking trips, Staffed property

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Price per night from

$1,076

Grove House, villa with swimming pool

San Venanzo villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 24 minutes

3 of 4 match: Trampoline, Walking trips, Boat available, Staffed property

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Price per night from

$284

Casale dei Pianetti

Sovana farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Staffed property, Boat available, Walking trips, Trampoline

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Price per night from

$185

Country house Il fornello APP. Hawthorn

Citta della Pieve farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Staffed property, Boat available, Walking trips, Trampoline

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Camera n2 Gelso

Barberino Tavarnellle private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Boat available, Trampoline, Walking trips, Staffed property

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Price per night from

$93

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, Walking trips, Trampoline

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Price per night from

$124

Canonici

Montecastrilli villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 11

2 of 4 match: Staffed property, Boat available, Walking trips, Trampoline

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Stay in a medieval tower in Siena! Apt for two.

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Boat available, Trampoline, Walking trips, Staffed property

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Price per night from

$124

Farm Humile - Suite "Solevante"

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Boat available, Trampoline, Walking trips, Staffed property

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Price per night from

$222

Agriturismo Humile - Suite "Lunaspicchio"

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Boat available, Trampoline, Walking trips, Staffed property

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Price per night from

$222

Discount Flavia Constans

Spello farmhouse

  • 3 bedrooms
  • 7 bathrooms
  • sleeps 9

2 of 4 match: Boat available, Trampoline, Walking trips, Staffed property

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Borgo di Mezzo

Castelnuovo dell'Abate apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 49 minutes

2 of 4 match: Boat available, Trampoline, Walking trips, Staffed property

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Price per night from

$111

Farmhouse Santa Maria - Chamber of Pierisa

Montefollonico farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 29 minutes

2 of 4 match: Boat available, Trampoline, Walking trips, Staffed property

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Price per night from

$74

Farmhouse Santa Maria - Grandpa's House

Montefollonico farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 29 minutes

2 of 4 match: Boat available, Trampoline, Walking trips, Staffed property

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Price per night from

$74

Viewing 38 of 2,181
rentals in Montepulciano

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