Vacation Rentals & Villas in Montepulciano

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2,561 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.

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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

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$1,700

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$465

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$379

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$514

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$576

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Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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

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Price per night from

$136

Il Paluffo B&B Blue Room

Certaldo b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

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Price per night from

$225

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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$265

La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

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

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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), Safe, Staffed property

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Price per night from

$222

Bed & Breakfast Il Paradiso

Capolona b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

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$87

Bed and Breakfast Paradise-The Tabaccaia

Capolona apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$130

Farm Humile - Suite "Solevante"

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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

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$222

Lake, countryside, relaxation and healthy food

Magione apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

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Soarzio apartment with pool near San Gimignano 4

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$124

La Scuderia Casa Vacanze

Arezzo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$197

Baita

Perugia farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

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Price per night from

$136

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

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Price per night from

$610

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), Safe, Staffed property, Trampoline

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Price per night from

$739

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

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

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

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Price per night from

$493

Casa dell'Istrice - Poggio Cennina Country Resort

Bucine house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$185

Walnut

Passignano Sul Trasimeno bungalow

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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2 Bedroom, 2 bathroom, Quiet , Elegant Villa with pool - sleeps 4 + 2

Cortona apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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$438

3 bedroom, 3 bathroom, spacious apartment with pool - sleeps 6 +1

Cortona house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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

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Price per night from

$493

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

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Price per night from

$271

Chalet Perugia Podere Caldaruccio

Perugia apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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

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Price per night from

$241

1 Bedroom, 1 bathroom apartment with Pool - sleeps 2 + 2

Cortona farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$210

Villa del Falco - Poggio Cennina Country Resort

Bucine villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$699

Villa della Volpe - Poggio Cennina Country Resort

Bucine villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$699

Casa della Lepre - Poggio Cennina Country Resort

Bucine house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$661

Casa del Merlo - Poggio Cennina Country Resort

Bucine house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

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Price per night from

$466

Casa del Lupo - Poggio Cennina Country Resort

Bucine house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

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Price per night from

$466

Casa del Cinghiale - Poggio Cennina Country Resort

Bucine house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

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Price per night from

$466

Casa del Riccio - Poggio Cennina Country Resort

Bucine house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$285

Viewing 38 of 2,561
rentals in Montepulciano

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