Vacation Rentals & Villas in Montepulciano

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2,289 Houses

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.

Match: Shared outdoor pool (unheated) Games room 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!

Match: Shared outdoor pool (unheated) Games room 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

Match: Shared outdoor pool (unheated) Games room Staffed property Trampoline

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Price per night from

$1,695

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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), Games room, Staffed property, Trampoline

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$86

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Games room, Shared outdoor pool (unheated), Staffed property, Trampoline

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$135

Ripostena 9

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$1,231

Fattoria Borgonuovo - Rosa

Cortona lodge

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Games room, Trampoline

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Price per night from

$122

Fattoria Borgonuovo - Ortensia

Cortona lodge

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Games room, Trampoline

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Price per night from

$122

Fattoria Borgonuovo - Geranio

Cortona lodge

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Games room, Trampoline

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$122

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Games room, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$377

La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

3 of 4 match: Games room, Shared outdoor pool (unheated), 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: Games room, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$264

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Games room, Shared outdoor pool (unheated), 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: Games room, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$512

BUCCIA NERA bilo1

Arezzo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$185

CASALE DELLE LUCREZIE

Todi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$99

Appartamento Bilocale con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$121

Appartamento Trilocale A con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$128

Ripostena 6-the dryer

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$1,231

Ripostena 10

Casole d'Elsa townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$1,231

Ripostena 11 the barn

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$1,231

Ripostena-5 The Remittance

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$1,231

Ripostena 7-Trinciatoio

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$1,231

Tenuta i Lecci di Gurian Roberta - Il Cipresso

Terranuova Bracciolini farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$92

Le Stalle, Podere Patrignone

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$264

BUCCIA NERA bilo3

Arezzo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$185

CARPE DIEM LIVING CLUB ASSISI.

Armenzano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Farmhouse "Le Case" with 3 apartments + double bedroom and extra bed

Gubbio house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 26 minutes

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$99

Antico Borgo Ripostena - 8 Casa Vecchia

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$1,231

Ripostena-Melissa House 1

Casole d'Elsa house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Games room, Staffed property

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Price per night from

$1,231

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Games room, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$463

Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Shared outdoor pool (unheated), Staffed property, Games room, Trampoline

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Price per night from

$185

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Shared outdoor pool (unheated), Staffed property, Games room, Trampoline

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Price per night from

$160

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

3 of 4 match: Games room, Shared outdoor pool (unheated), 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, Games room, Shared outdoor pool (unheated), Trampoline

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Price per night from

$74

House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

  • 13 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Staffed property, Games room, Shared outdoor pool (unheated), Trampoline

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Price per night from

$123

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: Shared outdoor pool (unheated), Games room, Staffed property, Trampoline

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Price per night from

$307

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Shared outdoor pool (unheated), Games room, Staffed property, Trampoline

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Price per night from

$307

Viewing 38 of 2,289
rentals in Montepulciano

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