Vacation Rentals & Villas in Montepulciano

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2,469 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) Table tennis 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) Table tennis 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

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$1,701

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$265

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Tipical rural cottage in Tuscany hills

Scansano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Table tennis, Trampoline

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$74

House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

  • 13 bedrooms
  • 1 bathroom
  • sleeps 5

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Table tennis, Trampoline

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$124

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Shared outdoor pool (unheated), Table tennis, Staffed property, Trampoline

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$87

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Table tennis, Shared outdoor pool (unheated), Staffed property, Trampoline

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$136

Ripostena 9

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Table tennis, Staffed property

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Price per night from

$1,233

Earth Etruria Il Fienile

Terranuova Bracciolini townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Table tennis, Staffed property

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Price per night from

$321

Land Minister Apartment Etruria

Terranuova Bracciolini townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Table tennis, Staffed property

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Price per night from

$309

Tuscan Villa Argiano 1 room,Montepulciano, B&B

Montepulciano villa

  • 4 bedrooms
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Table tennis, Staffed property

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$81

CASINA PRIMA - FARM CYPRESS - BUCINE TUSCANY ITALY

Bucine villa

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Table tennis, Staffed property

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$124

Casa San Carlo - apartment Trasimeno

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Table tennis, Trampoline

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$136

Casa San Carlo - apartment Bolsena

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Table tennis, Trampoline

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Price per night from

$124

Casa San Carlo - apartment Monteleone

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Table tennis, Trampoline

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Price per night from

$111

Casa San Carlo - Studio apartment Giulia

Monteleone d'Orvieto studio

  • Studio
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Table tennis, Trampoline

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Price per night from

$111

Agriturismo la Coccinella

Poggioni apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Table tennis, Trampoline

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$198

Casa San Carlo - apartment Città della Pieve

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Table tennis, 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

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Table tennis, Trampoline

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Price per night from

$148

Antica Quercia Verde Cortona - a Tuscan Dream 1

Cortona house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Table tennis, Trampoline

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Price per night from

$141

Fattoria Borgonuovo - Rosa

Cortona lodge

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Table tennis, 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), Table tennis, 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), Table tennis, Trampoline

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Price per night from

$122

Agriturismo la Coccinella

Poggioni apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Shared outdoor pool (unheated), Table tennis, Trampoline

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Price per night from

$173

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Table tennis, Shared outdoor pool (unheated), 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: Table tennis, Shared outdoor pool (unheated), 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: Table tennis, Shared outdoor pool (unheated), 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: Table tennis, Shared outdoor pool (unheated), Staffed property, Trampoline

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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), Table tennis, 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), Table tennis, Staffed property

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Price per night from

$129

Farm Caliano

Asciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 54 minutes

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Table tennis, Staffed property

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Price per night from

$185

Ripostena-5 The Remittance

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Table tennis, Staffed property

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Price per night from

$1,233

Ripostena 6-the dryer

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Table tennis, Staffed property

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Price per night from

$1,233

Ripostena 7-Trinciatoio

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Table tennis, Staffed property

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Price per night from

$1,233

Ripostena 11 the barn

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Table tennis, Staffed property

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Price per night from

$1,233

Ripostena 10

Casole d'Elsa townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Table tennis, Staffed property

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Price per night from

$1,233

Vacation Apartment Casole d'Elsa

Monteguidi apartment

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

3 of 4 match: Trampoline, Shared outdoor pool (unheated), Table tennis, Staffed property

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Price per night from

$444

Viewing 38 of 2,469
rentals in Montepulciano

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