Vacation Rentals & Villas in Montepulciano

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2,243 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: Climbing frame Shared outdoor pool (unheated) 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: Climbing frame Shared outdoor pool (unheated) 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: Climbing frame Shared outdoor pool (unheated) Staffed property Trampoline

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Price per night from

$1,695

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

Match: Climbing frame Shared outdoor pool (unheated) Staffed property Trampoline

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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), Climbing frame, Staffed property, Trampoline

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$86

Beautiful 2-bedroom apartment villa in the heart of Chianti, pool & sunset views

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Ideal Tuscany accomodation” We spent five glorious days at Patrignone. We loved the location, perfect for visiting many of the small towns, and also Florence and Siena. Our 2 bedroom villa was beautiful, and everything we could have wanted. We especially enjoyed the wonderful hospitality of Simon and Verity, and their three sons. It made the holiday extra special. We will definitely be back.

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

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$295

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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

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$135

Casa San Carlo - apartment Città della Pieve

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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

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$154

Casa San Carlo - apartment San Casciano

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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$148

Casa San Carlo - apartment Trasimeno

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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$135

Casa San Carlo - apartment Bolsena

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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

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$123

Casa San Carlo - apartment Monteleone

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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$111

Chiesa di San Silvestro dei Pecorari Appartamenti vacanza Lisa

Piobbico apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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$123

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$264

La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

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

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the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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

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Price per night from

$512

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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

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$377

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

Cortona farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$209

Farmhouse Apartments with Pool in Quiet Rural Setting - Pietramelina

Pierantonio apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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

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Price per night from

$84

Santa Chiara - Pietramelina

Pierantonio apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

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Price per night from

$148

Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Staffed property, Shared outdoor pool (unheated), Climbing frame, 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: Staffed property, Shared outdoor pool (unheated), Climbing frame, Trampoline

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Price per night from

$160

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$463

Oleanders-The Barn

Castelfiorentino barn

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 5

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

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Price per night from

$209

Oleanders-The Old House

Castelfiorentino house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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

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Price per night from

$172

Casa San Carlo - apartment Orvieto

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Staffed property, Shared outdoor pool (unheated), Climbing frame, Trampoline

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Price per night from

$148

2 of 4 match: Staffed property, Shared outdoor pool (unheated), Climbing frame, Trampoline

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Price per night from

$387

House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

  • 13 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Climbing frame, Staffed property, Shared outdoor pool (unheated), Trampoline

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Price per night from

$123

Tipical rural cottage in Tuscany hills

Scansano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Climbing frame, Staffed property, Shared outdoor pool (unheated), Trampoline

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Price per night from

$74

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Climbing frame, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$307

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: Climbing frame, Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$307

Farmhouse Apartments with Pool in Quiet Rural Location - Rancale

Pierantonio apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Shared outdoor pool (unheated), Trampoline, Climbing frame, Staffed property

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Price per night from

$128

La Casa di Piandelbello

Migliano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Staffed property, Trampoline, Climbing frame, Shared outdoor pool (unheated)

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CASTELLO DI MONTALTO - 2 bedroom Villa in Chianti

Castelnuovo Berardenga house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Staffed property, Trampoline, Climbing frame, Shared outdoor pool (unheated)

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Price per night from

$284

Casa Anna

Terranuova Bracciolini apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

2 of 4 match: Staffed property, Trampoline, Climbing frame, Shared outdoor pool (unheated)

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Price per night from

$350

Il Paluffo B&B Blue Room

Certaldo b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Climbing frame, Staffed property, Shared outdoor pool (unheated), Trampoline

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Price per night from

$224

Viewing 38 of 2,243
rentals in Montepulciano

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