Vacation Rentals & Villas in Montepulciano

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Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

Match: Climbing frame Private outdoor pool (heated) Staffed property Trampoline

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Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Private outdoor pool (heated), Climbing frame, Staffed property, Trampoline

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$86

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: Private outdoor pool (heated), Climbing frame, Staffed property, Trampoline

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$183

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: Private outdoor pool (heated), Climbing frame, Staffed property, Trampoline

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Price per night from

$604

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

3 of 4 match: Private outdoor pool (heated), Climbing frame, Staffed property, Trampoline

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$1,682

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Climbing frame, Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$732

Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$183

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$159

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.

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$293

Casa San Carlo - apartment Orvieto

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$147

Casa San Carlo - apartment Città della Pieve

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$153

Casa San Carlo - apartment San Casciano

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$147

Casa San Carlo - apartment Trasimeno

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$134

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$384

Casa San Carlo - apartment Bolsena

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$122

Casa San Carlo - apartment Monteleone

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$110

Casa San Carlo - Studio apartment Giulia

Monteleone d'Orvieto studio

  • Studio
  • 1 bathroom
  • sleeps 4

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$110

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, Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$305

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Climbing frame, Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$305

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

2 of 4 match: Climbing frame, Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$134

Meravigliosa villa con piscina e idromassaggio

Massa Martana villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 4 match: Climbing frame, Staffed property, Private outdoor pool (heated), Trampoline

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Price per night from

$549

Farmhouse Apartments with Pool in Quiet Rural Location - Rancale

Pierantonio apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Private outdoor pool (heated), Trampoline, Climbing frame, Staffed property

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Price per night from

$127

Chiesa di San Silvestro dei Pecorari Appartamenti vacanza Lisa

Piobbico apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Private outdoor pool (heated), Trampoline, Climbing frame, Staffed property

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$122

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Climbing frame, Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$262

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 4 match: Climbing frame, Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$375

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 4 match: Climbing frame, Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$569

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Climbing frame, Private outdoor pool (heated), Staffed property, Trampoline

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La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

2 of 4 match: Climbing frame, Private outdoor pool (heated), Staffed property, Trampoline

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Casale panoramicissimo con piscina S. Damiano

Todi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 4 match: Climbing frame, Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$110

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Climbing frame, Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$509

Comfort under the Umbrian Sun! Pool and Air Conditioned!!

Spoleto villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$451

Poggerina luxury private villa with stunning view

Greve in Chianti villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Beautiful location and villa, gracious and helpful hosts” I researched extensively before choosing this villa and it more than met our expectations. From the first email Emanuele and his family provided excellent service and were accessible and helpful. Moreover, they made us feel like more than paying guests, more like friends. The villa itself was very spacious and roomy, with a kitchen that had everything we needed. The views are spectacular, and it's quiet and peaceful. I would recommend doing both the pizza night and the cooking night. Both were excellent. Our stay couldn't have been any better. We would highly recommend this villa.

Responds fast! avg. 3 hours 16 minutes

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$610

Villa Borgo Taverne

Corciano villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$696

Holiday House Villa Patty

Apecchio guest house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 34 minutes

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$122

San Carlo house

Monteleone d'Orvieto villa

  • 10 bedrooms
  • 7 bathrooms
  • sleeps 32

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$2,133

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

Cortona farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Staffed property, Private outdoor pool (heated), Climbing frame, Trampoline

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Price per night from

$208

Suite CielAzzurro

Arezzo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Climbing frame, Trampoline, Private outdoor pool (heated), Staffed property

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Price per night from

$74

In Tuscany farm holidays

Radicondoli farmhouse

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

2 of 4 match: Private outdoor pool (heated), Trampoline, Climbing frame, Staffed property

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Price per night from

$427

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rentals in Montepulciano

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