Vacation Rentals & Villas in Montepulciano

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2,253 Houses

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

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Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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

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$136

RELAIS CAMPIGLIONI

Montevarchi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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$111

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), Shared outdoor pool (unheated), Staffed property, Trampoline

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$265

La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

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

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the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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

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

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Price per night from

$378

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

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$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, Shared outdoor pool (heated), Shared outdoor pool (unheated), Staffed property

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$172

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), Shared outdoor pool (unheated), Staffed property, Trampoline

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$185

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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

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Price per night from

$1,696

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), Shared outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$610

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$464

ORCHID

Capodacqua b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$111

Luxury Villa Pierle

Cortona villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

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

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Price per night from

$1,595

Camera classic (2 people) - Umbria

Citta di Castello b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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$85

Tipical rural cottage in Tuscany hills

Scansano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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$74

House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

  • 13 bedrooms
  • 1 bathroom
  • sleeps 5

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

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$123

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Shared outdoor pool (heated), Shared outdoor pool (unheated), 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

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

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Price per night from

$308

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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$86

Amazing Assisi

Assisi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$437

Beautiful 2-bedroom apartment villa in the heart of Chianti, pool & sunset views

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Ideal Tuscany accomodation” We spent five glorious days at Patrignone. We loved the location, perfect for visiting many of the small towns, and also Florence and Siena. Our 2 bedroom villa was beautiful, and everything we could have wanted. We especially enjoyed the wonderful hospitality of Simon and Verity, and their three sons. It made the holiday extra special. We will definitely be back.

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

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Price per night from

$295

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, Shared outdoor pool (unheated), Trampoline

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Price per night from

$224

Fattoria Quercia al Poggio - Apartment Cappella 4

Barberino Val d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$99

Fattoria Quercia al Poggio - Apartment Cappella 2

Barberino Val d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$182

"MARGHERITA", DOUBLE WITH TERRACE IN SAN GIMIGNANO

San Gimignano farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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$87

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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

Ospedalicchio apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$111

Antico Casale di Scansano

Scansano hotel apartment

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 4

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

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Suite deluxe (2/3 people) - Umbria

Citta di Castello b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

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Price per night from

$159

Junior suite (2 people) - Umbria

Citta di Castello b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$110

Dependence on Biribino (8 people) - Umbria

Citta di Castello house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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

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Price per night from

$296

Apartment Venus (4 people) - Umbria

Citta di Castello apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$147

Casa San Carlo - apartment Città della Pieve

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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

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Price per night from

$154

Casa San Carlo - apartment San Casciano

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$148

Antica Quercia Verde Cortona - a Tuscan Dream 1

Cortona house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$140

Villa Rosa dei Venti - Aliseo Cottage

Cortona cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

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Price per night from

$283

Viewing 38 of 2,253
rentals in Montepulciano

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