Vacation Rentals & Villas in Montepulciano

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868 Houses

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated) Staffed property Trampoline

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$742

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

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Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$87

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$137

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$310

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 44 minutes

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$310

Meravigliosa villa con piscina e idromassaggio

Massa Martana villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Staffed property, Private outdoor pool (heated), Trampoline

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Price per night from

$558

Casale panoramicissimo con piscina S. Damiano

Todi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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$112

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$266

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$380

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$578

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$516

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: 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 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Suite CielAzzurro

Arezzo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Trampoline, Private outdoor pool (heated), Staffed property

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$75

Holiday Villa in Cortona

Cortona villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

Responds fast! avg. 25 minutes

2 of 3 match: Staffed property, Private outdoor pool (heated), Trampoline

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Price per night from

$693

Siena San Fabiano climatized villa with outdoor heated pool

Monteroni d'Arbia villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

“Perfect combo of charm, location & comfort in glorious Tuscany!” We first dicovered San Fabiano in summer 2003 and have made it a point to return with family and friends as often as we can ever since! The location is ideal for exploring Siena, all the hill towns of southern tuscany, the Chianti and even great for easy day trips to Florence. Besides the charm of this renovated farmhouse - it also has modenr comforts like ac, screened windows, kitchenettes in all the rooms and wireless internet - plus a swimming pool! We love walking into the little town of Monteroni for our morning cappucinos and hiking the trails around this lovely farm estate. Great for kids and family gatherings as well as couples. We get through New England winters by dreaming of returning to San Fabiano. Highly recommended!

2 of 3 match: Staffed property, Private outdoor pool (heated), Trampoline

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Price per night from

$1,237

VILLA TALCIONA

Poggibonsi apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 12

2 of 3 match: Staffed property, Private outdoor pool (heated), Trampoline

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Price per night from

$192

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

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$496

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$467

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.

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$186

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!

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$613

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$1,707

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$1,361

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$1,237

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

2 of 3 match: Private outdoor pool (heated), Staffed property, Trampoline

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Price per night from

$1,626

2 of 3 match: Trampoline, Private outdoor pool (heated), Staffed property

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Price per night from

$1,843

Po' del Vento:è tutto intorno a te:16, piscina riscaldata, parco giochi, camino

Citta della Pieve guest house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

2 of 3 match: Trampoline, Private outdoor pool (heated), Staffed property

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Price per night from

$1,114

Exclusive Villa in countryside 8pers., heatable pool, Umbria/Tuscany, historic

Citta della Pieve villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Trampoline, Private outdoor pool (heated), Staffed property

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Price per night from

$620

Villa Rovicciano, sleeps 16+4. Family reunions, cooking service, heatable pool

Castel Ritaldi villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 20

2 of 3 match: Trampoline, Private outdoor pool (heated), Staffed property

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Price per night from

$1,488

Il Felceto - luxury 6 BDA villa with heated pool

Citta della Pieve villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

2 of 3 match: Trampoline, Private outdoor pool (heated), Staffed property

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Price per night from

$992

The Granary, villa with pool and heated spa

San Venanzo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 12 minutes

2 of 3 match: Trampoline, Private outdoor pool (heated), Staffed property

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Price per night from

$229

Historic Villa Biribino (27 people) - Umbria

Citta di Castello b&b

  • 9 bedrooms
  • 21 bathrooms
  • sleeps 25

2 of 3 match: Trampoline, Private outdoor pool (heated), Staffed property

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Price per night from

$1,336

Villa Castellare de Sernigi stunning sunsets for 13/14 people

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

2 of 3 match: Trampoline, Private outdoor pool (heated), Staffed property

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Price per night from

$1,414

Exclusive luxury villa in the Tuscan countryside. 14 rooms, pool, A/C and Wi-Fi!

Monticiano villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 28

2 of 3 match: Trampoline, Private outdoor pool (heated), Staffed property

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Price per night from

$3,611

Villa Miralaghi 8-9 WI-FI, Biliardo, Camino, Piscina riscaldata, Jacuzzi, Bocce

Citta della Pieve house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

2 of 3 match: Trampoline, Private outdoor pool (heated), Staffed property

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Price per night from

$1,114

#la Ghibellina2 Montalcino

Montalcino house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Private outdoor pool (heated), Trampoline, Staffed property

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Price per night from

$75

VILLA SARGIANO Suite Familiare Michelangelo

Arezzo villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Private outdoor pool (heated), Trampoline, Staffed property

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Price per night from

$160

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rentals in Montepulciano

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