Vacation Rentals & Villas in Montepulciano

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2,572 Houses

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

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agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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$307

Amazing Assisi

Assisi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Shared outdoor pool (heated), Iron, Trampoline

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$436

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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$264

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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$512

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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$574

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

3 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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Price per night from

$377

Casale panoramicissimo con piscina S. Damiano

Todi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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$111

Tenuta I Terzi d Ombrone

Poggi del Sasso villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

3 of 4 match: Trampoline, Shared outdoor pool (heated), Iron, Staffed property

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Price per night from

$3,241

"Olivo Junior". Charming apartment in Podere Pietreta, old farmhouse with pool

Radicofani apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

3 of 4 match: Trampoline, Shared outdoor pool (heated), Iron, Staffed property

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Price per night from

$172

Borgo di Vagli

Mercatale di Cortona house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 36 minutes

3 of 4 match: Trampoline, Shared outdoor pool (heated), Iron, Staffed property

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$167

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

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

3 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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$493

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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Price per night from

$1,613

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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Price per night from

$737

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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Price per night from

$463

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: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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Price per night from

$184

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: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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Price per night from

$608

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

3 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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Price per night from

$1,694

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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$1,350

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, Shared outdoor pool (heated), Iron, Staffed property

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Price per night from

$329

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, Shared outdoor pool (heated), Iron, Staffed property

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Price per night from

$1,031

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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$87

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

2 of 4 match: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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$136

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: Shared outdoor pool (heated), Iron, Staffed property, Trampoline

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Price per night from

$307

RELAIS CAMPIGLIONI

Montevarchi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Staffed property, Iron, Shared outdoor pool (heated), Trampoline

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Price per night from

$111

Canonici

Montecastrilli villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 11

2 of 4 match: Shared outdoor pool (heated), Staffed property, Iron, Trampoline

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Casale dei Pianetti

Sovana farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Shared outdoor pool (heated), Staffed property, Iron, Trampoline

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Price per night from

$184

Cascina Toscana -Luxury Holiday House- Private Swimmingpool & Jacuzzi

Arezzo villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Shared outdoor pool (heated), Staffed property, Iron, Trampoline

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Price per night from

$614

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

Ospedalicchio apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Iron, Trampoline, Shared outdoor pool (heated), Staffed property

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Price per night from

$111

Casa San Carlo - apartment Orvieto

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Shared outdoor pool (heated), Staffed property, Iron, Trampoline

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Price per night from

$148

Il Paluffo B&B Blue Room

Certaldo b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Shared outdoor pool (heated), Staffed property, Iron, Trampoline

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Price per night from

$224

Farm House Erika Porcine

Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 12 minutes

2 of 4 match: Shared outdoor pool (heated), Staffed property, Iron, Trampoline

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Price per night from

$111

Farm House Porcine Desire

Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 12 minutes

2 of 4 match: Shared outdoor pool (heated), Staffed property, Iron, Trampoline

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Price per night from

$111

VILLA SARGIANO - Suite Matrimoniale Caminetto

Arezzo villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Shared outdoor pool (heated), Trampoline, Iron, Staffed property

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Price per night from

$141

YourTuscanLoft LowCost B&B SmartTraveller

Sinalunga studio

  • Studio
  • 2 bathrooms
  • sleeps 3

2 of 4 match: Shared outdoor pool (heated), Trampoline, Iron, Staffed property

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Price per night from

$37

Ground floor apartment for 2 in Tuscan countryside

San Rocco a Pilli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Shared outdoor pool (heated), Trampoline, Iron, Staffed property

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Price per night from

$172

Viewing 38 of 2,572
rentals in Montepulciano

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