Vacation Rentals & Villas in Montepulciano

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il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Cot available Bicycles available 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: Cot available Bicycles available Staffed property Trampoline

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Price per night from

$379

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Cot available Bicycles available Staffed property Trampoline

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Il Paluffo B&B Blue Room

Certaldo b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Staffed property, Cot available, Bicycles available, Trampoline

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Price per night from

$225

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Cot available, Bicycles available, Staffed property, Trampoline

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Price per night from

$308

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Cot available, Bicycles available, Staffed property, Trampoline

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Price per night from

$87

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Cot available, Bicycles available, Staffed property, Trampoline

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Price per night from

$136

Discount Flavia Constans

Spello farmhouse

  • 3 bedrooms
  • 7 bathrooms
  • sleeps 9

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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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: Cot available, Bicycles available, 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: Cot available, Bicycles available, 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: Cot available, Bicycles available, Staffed property, Trampoline

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Price per night from

$576

Antica dimora

Monteroni d'Arbia apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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Price per night from

$79

Three Mills Farm

Casole d'Elsa apartment

  • 1 bedroom
  • 4 bathrooms
  • sleeps 2

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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Price per night from

$124

Casa Mila Garden Apartment

Sansepolcro apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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Price per night from

$93

Villa Borgo Taverne

Corciano villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

3 of 4 match: Staffed property, Cot available, Bicycles available, Trampoline

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Price per night from

$704

3 of 4 match: Staffed property, Cot available, Bicycles available, Trampoline

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Price per night from

$529

Siena Entire Tuscan Property 20P Private pool A/C Hottub wifi OutdoorKitchen

Sovicille villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 20

3 of 4 match: Staffed property, Cot available, Bicycles available, Trampoline

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Price per night from

$985

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: Cot available, Bicycles available, 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!

3 of 4 match: Cot available, Bicycles available, 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: Cot available, Bicycles available, Staffed property, Trampoline

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Price per night from

$1,701

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Cot available, Bicycles available, 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: Cot available, Bicycles available, Staffed property, Trampoline

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Price per night from

$1,620

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

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

3 of 4 match: Bicycles available, Cot available, Staffed property, Trampoline

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Price per night from

$493

Farmhouse in old mill in the Chianti hills

Monteriggioni house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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Price per night from

$148

Lilla

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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Price per night from

$89

Ancient Chianti home with private garden and lake

Radda in Chianti farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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Price per night from

$117

Borgo di Vagli

Mercatale di Cortona house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 1 minutes

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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Price per night from

$168

Podere Le Cantine

Lucignano farmhouse

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 28

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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CISPIANO AGRITURISM IL CELLESE

Castellina In Chianti farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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NICCHIE AGRITURISMO IL CELLESE

Castellina In Chianti farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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FORNO AGRITURISMO IL CELLESE

Castellina In Chianti farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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Wonderful and romantic Tuscany

Foiano Della Chiana villa

  • 12 bedrooms
  • 8 bathrooms
  • sleeps 30

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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Price per night from

$863

I Tigli, apt in farmhouse only 5 km to Montepulciano. 2 bedrooms, pool and Wi-Fi

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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Price per night from

$194

Agriturismo Podere San Giusto

Sovicille townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

3 of 4 filters match

Price per night from

$136

Newcastle upon sangiovanniinpoggio

Monteroni d'Arbia villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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Price per night from

$124

House "The three Muses"

Deruta b&b

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

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Price per night from

$62

B&B 4 rooms 18km Siena + Pool Casa Giulia

Siena b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 26 minutes

3 of 4 match: Trampoline, Cot available, Bicycles available, Staffed property

3 of 4 filters match

Price per night from

$87

Viewing 38 of 1,531
rentals in Montepulciano

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