Vacation Rentals & Villas in Montepulciano

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1,212 Houses

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

Match: Bicycles available Shared outdoor pool (heated) Staffed property Trampoline

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agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$309

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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$87

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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

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Price per night from

$136

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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

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Price per night from

$379

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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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), Bicycles available, Staffed property, Trampoline

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Price per night from

$265

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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

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Price per night from

$576

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

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Price per night from

$514

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

Radicofani apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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

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Price per night from

$173

Borgo di Vagli

Mercatale di Cortona house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 1 minutes

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

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Price per night from

$168

Tenuta I Terzi d Ombrone

Poggi del Sasso villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

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

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Price per night from

$3,242

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), Bicycles available, Staffed property, Trampoline

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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!

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

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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

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

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Price per night from

$1,701

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Shared outdoor pool (heated), 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

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

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Price per night from

$1,356

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$465

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, Bicycles available, Shared outdoor pool (heated), Staffed property

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Price per night from

$1,031

Tipical rural cottage in Tuscany hills

Scansano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$74

Country house Il fornello APP. Hawthorn

Citta della Pieve farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

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House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

  • 13 bedrooms
  • 1 bathroom
  • sleeps 5

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

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Price per night from

$124

Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$185

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$161

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, 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: Shared outdoor pool (heated), Trampoline, Bicycles available, Staffed property

2 of 4 filters match

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, Shared outdoor pool (heated), Bicycles available, Trampoline

2 of 4 filters match

Price per night from

$148

Il Paluffo B&B Blue Room

Certaldo b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

2 of 4 filters match

Price per night from

$225

Farm House Porcine Desire

Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 12 minutes

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

2 of 4 filters match

Price per night from

$111

Farm House Erika Porcine

Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 12 minutes

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

2 of 4 filters match

Price per night from

$111

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: Bicycles available, Shared outdoor pool (heated), Staffed property, Trampoline

2 of 4 filters match

Price per night from

$309

RELAIS CAMPIGLIONI

Montevarchi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

2 of 4 filters match

Price per night from

$111

Amazing Assisi

Assisi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

2 of 4 filters match

Price per night from

$438

Casa Azalea

Certaldo Alto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 4 match: Staffed property, Shared outdoor pool (heated), Trampoline, Bicycles available

1 of 4 filters match

Price per night from

$144

Casina

Certaldo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 4 match: Staffed property, Shared outdoor pool (heated), Trampoline, Bicycles available

1 of 4 filters match

Price per night from

$102

Casa Dante

Certaldo apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 4 match: Staffed property, Shared outdoor pool (heated), Trampoline, Bicycles available

1 of 4 filters match

Price per night from

$246

Oliveta

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 4 match: Staffed property, Shared outdoor pool (heated), Trampoline, Bicycles available

1 of 4 filters match

Price per night from

$154

Villa Rosa dei Venti - Aliseo Cottage

Cortona cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

2 of 4 filters match

Price per night from

$284

Viewing 38 of 1,212
rentals in Montepulciano

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