Vacation Rentals & Villas in Montepulciano

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1,122 Houses

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Heated pool Ceiling Fans Staffed property Trampoline

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Price per night from

$738

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agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Heated pool, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$308

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

3 of 4 match: Heated pool, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$308

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: Heated pool, Ceiling Fans, Staffed property, Trampoline

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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

3 of 4 match: Heated pool, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$1,697

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Heated pool, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$1,230

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Heated pool, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$1,616

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: Heated pool, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$610

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!

3 of 4 match: Staffed property, Heated pool, Ceiling Fans, Trampoline

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Price per night from

$1,230

Family vacation accommodation in Umbria L'Alba at Alsagra, Umbria Italy

San Giovanni del Pantano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Heated pool, Ceiling Fans, Staffed property

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Price per night from

$331

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

3 of 4 match: Ceiling Fans, Heated pool, Staffed property, Trampoline

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Villa Castellare de Sernigi stunning sunsets for 13/14 people

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

3 of 4 match: Trampoline, Heated pool, Ceiling Fans, Staffed property

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Price per night from

$2,108

Papaveri family holiday apartment in the heart of Italy

San Giovanni del Pantano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Heated pool, Ceiling Fans, Staffed property

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Price per night from

$331

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

Monticiano villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 28

3 of 4 match: Trampoline, Heated pool, Ceiling Fans, Staffed property

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Price per night from

$3,590

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

Citta della Pieve villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Trampoline, Heated pool, Ceiling Fans, Staffed property

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Price per night from

$615

Walk to Town! Luxury Villa in Montepulciano, Tuscany w/ Pool & Spa!!

Montepulciano villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 58 minutes

3 of 4 match: Trampoline, Heated pool, Ceiling Fans, Staffed property

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Price per night from

$1,033

Il Felceto - luxury 6 BDA villa with heated pool

Citta della Pieve villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

3 of 4 match: Trampoline, Heated pool, Ceiling Fans, Staffed property

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Price per night from

$985

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Heated pool, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$86

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

2 of 4 match: Heated pool, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$136

B & B THE OLD Lieutenancy SUITE TRIPLE

Citta della Pieve b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 13 minutes

2 of 4 match: Heated pool, Trampoline, Ceiling Fans, Staffed property

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Price per night from

$99

2 MINI APPARTAMENTI ELEGANTI INDIPENDENTI CON PARCHEGGIO

San Martino in Colle house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 4 match: Heated pool, Trampoline, Ceiling Fans, Staffed property

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Price per night from

$80

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Heated pool, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$265

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Heated pool, Ceiling Fans, Staffed property, Trampoline

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La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

2 of 4 match: Heated pool, Ceiling Fans, Staffed property, Trampoline

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the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 4 match: Heated pool, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$575

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 4 match: Heated pool, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$378

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Heated pool, Ceiling Fans, Staffed property, Trampoline

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Price per night from

$514

RELAIS CAMPIGLIONI

Montevarchi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Staffed property, Ceiling Fans, Heated pool, Trampoline

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Price per night from

$111

Amazing Assisi

Assisi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Staffed property, Ceiling Fans, Heated pool, Trampoline

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Price per night from

$437

Meravigliosa villa con piscina e idromassaggio

Massa Martana villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 4 match: Staffed property, Ceiling Fans, Heated pool, Trampoline

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Price per night from

$554

Casa San Carlo - apartment Bolsena

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

2 of 4 match: Heated pool, Staffed property, Ceiling Fans, Trampoline

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Price per night from

$123

Casa San Carlo - apartment Monteleone

Monteleone d'Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Heated pool, Staffed property, Ceiling Fans, Trampoline

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Price per night from

$111

Casa vacanze a pochi km. da Assisi e Perugia con piscina, giardino

Ospedalicchio apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Ceiling Fans, Trampoline, Heated pool, Staffed property

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Price per night from

$111

Suite CielAzzurro

Arezzo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Ceiling Fans, Trampoline, Heated pool, Staffed property

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Price per night from

$74

Stones of the ancient village

San Lorenzo a Merse house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Heated pool, Trampoline, Ceiling Fans, Staffed property

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Price per night from

$129

2 of 4 match: Heated pool, Trampoline, Ceiling Fans, Staffed property

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Price per night from

$148

Farmhouse Santa Maria - Grandpa's House

Montefollonico farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 29 minutes

2 of 4 match: Heated pool, Trampoline, Ceiling Fans, Staffed property

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Price per night from

$74

Feriendomizil mit Aussichtspool mit Blick auf Assisi.

Limigiano house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Heated pool, Trampoline, Ceiling Fans, Staffed property

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Price per night from

$185

Viewing 38 of 1,122
rentals in Montepulciano

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