Vacation Rentals & Villas in Montepulciano

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34 Houses

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

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$1,033

Tuscany Villa in Montepulciano,Free Parking,Free Wi-fi,view of valley

Bivio di San Biagio villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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$309

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The Countess' Blue Suite

Montepulciano guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$198

Tuscan Villa Argiano 1 room,Montepulciano, B&B

Montepulciano villa

  • 4 bedrooms
  • 1 bathroom
  • sleeps 2

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$81

Villa Poggio Fagianino

Sant'Albino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$358

Holiday Apartment in the historical palace.Marina

Montepulciano apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

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$173

Casa Dei Ro.Gi. - Montepulciano - Tuscany

Abbadia di Montepulciano house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

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$79

Farmhouse Il Palazzo dei Diavoli Montepulciano - Tuscany Val d 'Orcia

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$149

I Tigli, apt in farmhouse only 5 km to Montepulciano. 2 bedrooms, pool and Wi-Fi

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$194

Il Molinaccio 14+2, Emma Villas

Cervognano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

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$1,011

Studio "Borghetto" at The House of the Oaks - Montepulciano

Montepulciano studio

  • Studio
  • 1 bathroom
  • sleeps 2

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$129

Apartment "Poggino" - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$185

Studio "Rustic" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$129

Poggio Etrusco: Tuscan B&B, apts, & Cooking School

Montepulciano villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

“Beyond adjectives” There is no way to describe our stay here! Pamela and Johnny were more than welcoming. We arrived with our 7 & 4 year olds in tow...and from The gate greeting, we felt as if we were at "memee's house". Each kid had a job...gate keeping and keeping track of the red fetch toy for Bella. We had an unwarranted snafu on credit card deposits in Rome the day before...but it was of no concern to these wonderful and true hosts... Each morning, The breakfast was true to Tuscany yet appealing to the kids... we were within an hours drive of each of our potential destinations...and each evening with a game of fetch watching Bella and the kids...the hosts helped us decide upon on the next days itinerary! We will be back with the whole family in July!

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$1,049

Apartment "The Hague" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$209

Apartment "Pratino" - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$172

Apartment "Belvedere" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$172

TASKO

Montepulciano villa

  • 5 bedrooms
  • 9 bathrooms
  • sleeps 9

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Price per night from

$1,235

Tenuta Senese Tenuta Senese

Montepulciano house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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$646

Great rentals within 20 miles that match your search

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

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$309

In Tuscany farm holidays

Radicondoli farmhouse

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

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$432

Stones of the ancient village

San Lorenzo a Merse house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$130

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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$186

Villa Castellare de Sernigi stunning sunsets for 13/14 people

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

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$2,115

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

Monticiano villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 28

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$3,603

. IL GLICINE - Enjoy the Tuscan - free WI-FI

Monteguidi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$89

Casa Vacanze "iL Roso". Casa singola con giardino privato in relax

Radicondoli house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$99

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 20

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$346

typical Tuscan House single

Colle di Val d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$149

Villa with private pool in the heart of Tuscany

Pieve A Presciano villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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$840

appartamento grazia centro storico

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$186

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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$1,704

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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$611

Casa San Gimi Perfect Location

San Gimignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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$104

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