Vacation Rentals & Villas in Montepulciano

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803 Houses

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Boat available Sauna Staffed property Trampoline

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Price per night from

$86

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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, Sauna, Trampoline

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Price per night from

$160

Three Arches House

Chiusi apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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

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Price per night from

$122

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

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

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Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$185

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: Boat available, Sauna, Staffed property, Trampoline

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Price per night from

$307

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$307

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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

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Price per night from

$135

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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

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Price per night from

$377

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Boat available, Sauna, 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, Sauna, 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

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

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Price per night from

$264

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

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Price per night from

$512

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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

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Price per night from

$575

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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

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Price per night from

$737

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.

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

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Price per night from

$185

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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

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Price per night from

$1,228

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

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

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Price per night from

$1,614

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

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

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

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Price per night from

$492

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

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

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Price per night from

$1,354

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!

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

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Price per night from

$609

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

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

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Price per night from

$1,698

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$464

Agriturismo Torre di Sant' Ansano

Ville di Corsano farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$99

Apartment antico casale Maremma

Roccastrada farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$99

Charming apartments in the Umbrian countryside

Cannara apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$111

CASALE DELLE LUCREZIE

Todi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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

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Price per night from

$99

In Tuscany farm holidays

Radicondoli farmhouse

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

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

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Price per night from

$430

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

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Price per night from

$1,830

CARPE DIEM LIVING CLUB ASSISI.

Armenzano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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

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Grove House, villa with swimming pool

San Venanzo villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 24 minutes

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

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Price per night from

$283

Authentic Villa in Trasimeno Lake

Monte del Lago villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

“Absolutely a beautiful place!” Location is great, peaceful,and both the house and the land are really well groomed..I liked so much the wood behind the house!! The house is so spacious, 3 apartments inside the main house...and everything is accurate and clean! The owner, Paolo, is a very kind and generous person who try to fulfill every request you ask him! The closest village where to buy food is only 10min by car. I highly recommend for short and long stay!!

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

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Price per night from

$1,343

ART-HANGAR BY TUSCAN-EXPERIENCE

Montalcino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

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Price per night from

$713

Villa Fada

Todi villa

  • 6 bedrooms
  • 9 bathrooms
  • sleeps 10

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

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Price per night from

$737

Exclusive luxury villa in the Tuscan countryside. 14 rooms, pool, A/C and Wi-Fi!

Monticiano villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 28

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

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Price per night from

$3,586

Villa Portoverde

Foiano Della Chiana villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

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

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Price per night from

$575

Case Sant'Anna 18 Posti

Pietraia villa

  • 9 bedrooms
  • 8 bathrooms
  • sleeps 18

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

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Price per night from

$1,116

#la Ghibellina2 Montalcino

Montalcino house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 4 match: Boat available, Sauna, Trampoline, Staffed property

1 of 4 filters match

Price per night from

$74

Viewing 38 of 803
rentals in Montepulciano

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