Vacation Rentals & Villas in Montepulciano

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2,665 Houses

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Boat available Microwave Staffed property Trampoline

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Price per night from

$87

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Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Boat available, Microwave, Trampoline

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Price per night from

$161

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: Boat available, Microwave, Staffed property, Trampoline

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Price per night from

$309

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Boat available, Microwave, Staffed property, Trampoline

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Price per night from

$309

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Boat available, Microwave, Staffed property, Trampoline

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Price per night from

$266

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Boat available, Microwave, Staffed property, Trampoline

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Price per night from

$1,621

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Boat available, Microwave, Staffed property, Trampoline

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Price per night from

$740

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: Boat available, Microwave, 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: Boat available, Microwave, Staffed property, Trampoline

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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

3 of 4 match: Boat available, Microwave, Staffed property, Trampoline

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Price per night from

$1,702

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Boat available, Microwave, Staffed property, Trampoline

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Price per night from

$1,357

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Boat available, Microwave, Staffed property, Trampoline

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Price per night from

$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: Boat available, Microwave, Staffed property, Trampoline

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Price per night from

$494

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

2 of 4 match: Boat available, Microwave, Staffed property, Trampoline

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Price per night from

$136

In Tuscany farm holidays

Radicondoli farmhouse

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

3 of 4 match: Trampoline, Boat available, Microwave, Staffed property

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Price per night from

$432

Three Arches House

Chiusi apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Boat available, Microwave, Staffed property

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Price per night from

$122

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Boat available, Microwave, Staffed property, Trampoline

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La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

2 of 4 match: Boat available, Microwave, Staffed property, Trampoline

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il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 4 match: Boat available, Microwave, Staffed property, Trampoline

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Price per night from

$379

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Boat available, Microwave, Staffed property, Trampoline

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Price per night from

$515

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 4 match: Boat available, Microwave, Staffed property, Trampoline

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Price per night from

$576

Cascina Toscana -Luxury Holiday House- Private Swimmingpool & Jacuzzi

Arezzo villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Boat available, Staffed property, Microwave, Trampoline

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Price per night from

$617

Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Boat available, Staffed property, Microwave, Trampoline

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Price per night from

$185

Grove House, villa with swimming pool

San Venanzo villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 24 minutes

3 of 4 match: Trampoline, Boat available, Microwave, Staffed property

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Price per night from

$284

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Boat available, Microwave, Staffed property, Trampoline

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Price per night from

$465

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: Boat available, Staffed property, Microwave, Trampoline

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Price per night from

$296

Farm Beautiful Braid

Cannara farmhouse

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

2 of 4 match: Boat available, Staffed property, Microwave, Trampoline

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Price per night from

$420

Antica Quercia Verde Cortona - a Tuscan Dream 1

Cortona house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Boat available, Staffed property, Microwave, Trampoline

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Price per night from

$141

Agriturismo Gello - Villa with panoramic pool in Tuscany - Chianciano Terme

Chianciano Terme villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 22

2 of 4 match: Boat available, Staffed property, Microwave, Trampoline

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Price per night from

$705

RELAIS CAMPIGLIONI

Montevarchi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Boat available, Staffed property, Microwave, Trampoline

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Price per night from

$111

Baita

Perugia farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Boat available, Staffed property, Microwave, Trampoline

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Price per night from

$136

The VILLA of your dreams: FAMILY GROUPS, KIDS, FRIENDS and PETS - Siena: 12min

Monteriggioni villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 20

2 of 4 match: Boat available, Staffed property, Microwave, Trampoline

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Price per night from

$518

2 of 4 match: Boat available, Staffed property, Microwave, Trampoline

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Price per night from

$389

Meravigliosa villa con piscina e idromassaggio

Massa Martana villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 4 match: Boat available, Staffed property, Microwave, Trampoline

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Price per night from

$555

Vila with private pool, air conditioning 10km from Orvieto

Orvieto villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 29 minutes

2 of 4 match: Boat available, Staffed property, Microwave, Trampoline

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Price per night from

$593

VILLA SARGIANO - Suite Matrimoniale Caminetto

Arezzo villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Boat available, Trampoline, Microwave, Staffed property

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Price per night from

$141

The Lumachella

Porano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Boat available, Trampoline, Microwave, Staffed property

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Price per night from

$99

Antica Canonica San Leolino

Panzano in Chianti apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Boat available, Trampoline, Microwave, Staffed property

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Price per night from

$204

Viewing 38 of 2,665
rentals in Montepulciano

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