Vacation Rentals & Villas in Montepulciano

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1,235 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.

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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!

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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

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$1,701

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$87

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Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$185

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$161

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$309

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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$136

Appartamento Bilocale con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$121

Appartamento Trilocale A con piscina sulle colline di Siena

Isola d'Arbia farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$129

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$379

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$265

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$576

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$514

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

3 of 4 match: Staffed property, Bicycles available, Games room, Trampoline

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Price per night from

$617

Casale Aiaccia

Arezzo farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$253

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

Sovicille villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 20

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$985

CARPE DIEM LIVING CLUB ASSISI.

Armenzano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Farmhouse "Le Case" with 3 apartments + double bedroom and extra bed

Gubbio house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 26 minutes

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$99

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Games room, Bicycles available, Staffed property, Trampoline

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Price per night from

$1,620

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

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$1,356

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$465

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

Citta della Pieve house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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$1,110

Poggio Rosemary - luxury farmhouse

Montespertoli farmhouse

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 8

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$1,233

Petrolo winery Villa. Events, weddings & large families. Service included

San Leolino villa

  • 16 bedrooms
  • 14 bathrooms
  • sleeps 33

3 of 4 match: Trampoline, Bicycles available, Games room, Staffed property

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Price per night from

$1,972

Casa Panorama Ad Est - Cooking class - Center of Italy

Perugia villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 18

Responds fast! avg. 50 minutes

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Price per night from

$56

Melia nest - Center Italy - Panorama Country

Perugia b&b

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 50 minutes

3 of 4 match: Trampoline, Bicycles available, Games room, Staffed property

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$56

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, Bicycles available, Games room, Staffed property

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$2,113

Molinvecchio

Vallea villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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$3,082

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

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Tipical rural cottage in Tuscany hills

Scansano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$74

Country house Il fornello APP. Hawthorn

Citta della Pieve farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

  • 13 bedrooms
  • 1 bathroom
  • sleeps 5

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$124

Ground floor apartment for 2 in Tuscan countryside

San Rocco a Pilli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Games room, Trampoline, Bicycles available, Staffed property

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Price per night from

$173

Historical Palace Buonaccorsi 13^ century: 4 bedrooms San Gimignano View WiFi

San Gimignano guest house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

2 of 4 match: Games room, Trampoline, Bicycles available, Staffed property

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Price per night from

$481

Casa San Carlo - apartment Orvieto

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Staffed property, Games room, Bicycles available, Trampoline

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Price per night from

$148

Viewing 38 of 1,235
rentals in Montepulciano

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