Vacation Rentals & Villas in Montepulciano

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3,787 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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$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

$611

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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$1,702

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$266

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Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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$136

La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

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il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$379

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$515

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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

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$576

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 32 minutes

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

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$309

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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$309

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$87

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.

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

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$296

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$465

Antica Quercia Verde Cortona - a Tuscan Dream 1

Cortona house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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$141

RELAIS CAMPIGLIONI

Montevarchi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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$111

Baita

Perugia farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$136

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

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$1,621

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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

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$740

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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$1,234

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 (unheated), Microwave, Staffed property, Trampoline

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$494

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

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

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$1,357

Lake, countryside, relaxation and healthy food

Magione apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

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Soarzio apartment with pool near San Gimignano 4

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$124

Antico Borgo di Sugame

Greve in Chianti farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$161

Ripostena 9

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$1,234

Agriturismo il Casalino - la Stalla

Casale di Pari farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 35 minutes

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

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$105

House Rosacanina VAT on Bioagriturismo. Riding, Pool, Tennis

Castiglion Fiorentino farmhouse

  • 13 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$124

Tipical rural cottage in Tuscany hills

Scansano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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$74

2 Bedroom, 2 bathroom, Quiet , Elegant Villa with pool - sleeps 4 + 2

Cortona apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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$438

Chalet Perugia Podere Caldaruccio

Perugia apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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

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$241

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

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$272

3 bedroom, 3 bathroom, spacious apartment with pool - sleeps 6 +1

Cortona house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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

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$494

1 Bedroom, 1 bathroom apartment with Pool - sleeps 2 + 2

Cortona farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$210

Vacation Apartment Casole d'Elsa

Monteguidi apartment

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

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

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Price per night from

$444

Three Mills Farm

Casole d'Elsa apartment

  • 1 bedroom
  • 4 bathrooms
  • sleeps 2

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

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Price per night from

$124

La Roccaia beautiful apartment near San Gimignano

Ulignano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$163

podere la giuda

Sinalunga apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

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Viewing 38 of 3,787
rentals in Montepulciano

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