Vacation Rentals & Villas in Montepulciano

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2,529 Houses

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Housekeeping Included Staffed property Trampoline

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Price per night from

$465

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Shared outdoor pool (unheated) Housekeeping Included Staffed property Trampoline

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Price per night from

$379

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (unheated) Housekeeping Included Staffed property Trampoline

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Price per night from

$576

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Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Shared outdoor pool (unheated), Housekeeping Included, Staffed property, Trampoline

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Price per night from

$87

Fattoria Quercia al Poggio - Apartment Cappella 4

Barberino Val d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$99

Fattoria Quercia al Poggio - Apartment Cappella 2

Barberino Val d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$183

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Housekeeping Included, Shared outdoor pool (unheated), 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: Housekeeping Included, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$265

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Housekeeping Included, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$514

La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

3 of 4 match: Housekeeping Included, Shared outdoor pool (unheated), Staffed property, Trampoline

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B & B Assisi from Poggio

Cannara b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$80

Fattoria Quercia al Poggio - Apartment Cappella 1

Barberino Val d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$197

Bed & Breakfast Il Paradiso

Capolona b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$87

Bed and Breakfast Paradise-The Tabaccaia

Capolona apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$130

Hotel Rosati

Chiusi b&b

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 3

Responds fast! avg. 3 hours 59 minutes

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$111

A horse in Tuscany for all the Family

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$124

Agriturismo Humile - Suite "Lunaspicchio"

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$222

Farm Humile - Agriculture and Hospitality B & B

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$222

Farm Humile - Suite "Solevante"

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$222

Ripostena 9

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$1,232

double room

Todi b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$87

#la Ghibellina2 Montalcino

Montalcino house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Shared outdoor pool (unheated), Trampoline, Housekeeping Included, Staffed property

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Price per night from

$74

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Shared outdoor pool (unheated), Housekeeping Included, Staffed property, Trampoline

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Price per night from

$739

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: Housekeeping Included, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$185

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

3 of 4 match: Housekeeping Included, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$1,700

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, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$610

Casa dell'Istrice - Poggio Cennina Country Resort

Bucine house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$661

Casa della Donnola - Poggio Cennina Country Resort

Bucine house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$285

Le Palazze, country b&b

Citta della Pieve b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 30 minutes

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$185

Il giardino degli elfi

Bevagna b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Casa Vacanze San Pierino -Stalla

Monteroni d'Arbia apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$247

4 People Apartment

Perugia farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$167

Apartment for 5 People

Perugia farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$197

CASALE DELLE LUCREZIE

Todi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$99

Ripostena 11 the barn

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$1,232

Ripostena 10

Casole d'Elsa townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$1,232

Ripostena 7-Trinciatoio

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$1,232

APARTMENT VILLA TADDEI 1 tuscany holiday

Certaldo apartment

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Housekeeping Included, Staffed property

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Price per night from

$555

Viewing 38 of 2,529
rentals in Montepulciano

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