Vacation Rentals & Villas in Montepulciano

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1,288 Houses

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Cot available Staffed property Swing set or jungle gym Trampoline

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Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Cot available, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$86

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Cot available, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$136

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Cot available, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$308

Agriturismo la Coccinella

Poggioni apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Cot available, Swing set or jungle gym, Trampoline

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Price per night from

$173

Agriturismo la Coccinella

Poggioni apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

3 of 4 match: Staffed property, Cot available, Swing set or jungle gym, Trampoline

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Price per night from

$198

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Cot available, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$265

Agriturismo "Casa al Gianni" - Capanna

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Cot available, Staffed property, Swing set or jungle gym

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Price per night from

$136

Agriturismo "Casa al Gianni" - Olmo

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Cot available, Staffed property, Swing set or jungle gym

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Price per night from

$148

Agriturismo "Casa al Gianni" - Fico

Siena apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Trampoline, Cot available, Staffed property, Swing set or jungle gym

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Price per night from

$161

Agriturismo Torre di Sant' Ansano

Ville di Corsano farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Cot available, Staffed property, Swing set or jungle gym

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Price per night from

$99

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Swing set or jungle gym, Cot available, Staffed property, Trampoline

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Price per night from

$379

Holiday House Villa Patty

Apecchio guest house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 34 minutes

3 of 4 match: Staffed property, Cot available, Swing set or jungle gym, Trampoline

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Price per night from

$124

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: Cot available, Staffed property, Swing set or jungle gym, 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: Cot available, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$1,701

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Cot available, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$1,356

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Cot available, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$1,620

Le Stalle, Podere Patrignone

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Trampoline, Cot available, Staffed property, Swing set or jungle gym

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Price per night from

$265

Santa Chiara - Pietramelina

Pierantonio apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Trampoline, Cot available, Staffed property, Swing set or jungle gym

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Price per night from

$148

3 of 4 match: Trampoline, Cot available, Staffed property, Swing set or jungle gym

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Price per night from

$124

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

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

3 of 4 match: Swing set or jungle gym, Cot available, Staffed property, Trampoline

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Price per night from

$492

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Swing set or jungle gym, Cot available, Staffed property, Trampoline

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Price per night from

$465

3 of 4 match: Trampoline, Cot available, Staffed property, Swing set or jungle gym

3 of 4 filters match

Price per night from

$161

Villa Portoverde

Foiano Della Chiana villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Trampoline, Cot available, Staffed property, Swing set or jungle gym

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Price per night from

$577

Oleanders-Casa Vacanze

Castelfiorentino barn

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 9

3 of 4 match: Trampoline, Cot available, Staffed property, Swing set or jungle gym

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Price per night from

$358

Oleanders-The Barn

Castelfiorentino barn

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 5

3 of 4 match: Trampoline, Cot available, Staffed property, Swing set or jungle gym

3 of 4 filters match

Price per night from

$210

Oleanders-The Old House

Castelfiorentino house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

3 of 4 match: Trampoline, Cot available, Staffed property, Swing set or jungle gym

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Price per night from

$173

Villa Miralaghi 8-9 WI-FI, Biliardo, Camino, Piscina riscaldata, Jacuzzi, Bocce

Citta della Pieve house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

3 of 4 match: Trampoline, Cot available, Staffed property, Swing set or jungle gym

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Price per night from

$1,110

Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Cot available, Staffed property, Swing set or jungle gym, Trampoline

2 of 4 filters match

Price per night from

$185

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 4 match: Cot available, Staffed property, Swing set or jungle gym, Trampoline

2 of 4 filters match

Price per night from

$160

Cascina Toscana -Luxury Holiday House- Private Swimmingpool & Jacuzzi

Arezzo villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Cot available, Staffed property, Swing set or jungle gym, Trampoline

2 of 4 filters match

Price per night from

$617

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

3 of 4 match: Cot available, Staffed property, Swing set or jungle gym, Trampoline

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Family Room

Castiglione del Lago apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Cot available, Trampoline, Staffed property, Swing set or jungle gym

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Price per night from

$99

Casa San Carlo - apartment Orvieto

Monteleone d'Orvieto apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Cot available, Staffed property, Swing set or jungle gym, Trampoline

2 of 4 filters match

Price per night from

$148

Il Palagione

Castellina In Chianti apartment

  • 5 bedrooms
  • 1 bathroom
  • sleeps 5

2 of 4 match: Cot available, Staffed property, Swing set or jungle gym, Trampoline

2 of 4 filters match

Price per night from

$308

Farm House Erika Porcine

Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 12 minutes

2 of 4 match: Cot available, Staffed property, Swing set or jungle gym, Trampoline

2 of 4 filters match

Price per night from

$111

Farm House Porcine Desire

Orvieto apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 3 hours 12 minutes

2 of 4 match: Cot available, Staffed property, Swing set or jungle gym, Trampoline

2 of 4 filters match

Price per night from

$111

Holiday house with 5 rooms and swimmingpool in the heart of Tuscany

Cavriglia farmhouse

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 15

2 of 4 match: Swing set or jungle gym, Trampoline, Cot available, Staffed property

2 of 4 filters match

Price per night from

$603

Viewing 38 of 1,288
rentals in Montepulciano

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