Vacation Rentals & Villas in Montepulciano

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1,212 Houses

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$86

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Le volte di ascesi

Assisi apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Housekeeping Included, Swing set or jungle gym, Trampoline

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Price per night from

$185

Le volte di ascesi 4

Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, Housekeeping Included, Swing set or jungle gym, Trampoline

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Price per night from

$160

agriturismo podere poggio mendico

Arezzo farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Housekeeping Included, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$307

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Housekeeping Included, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$135

Agriturismo Baciano - Appartamento Lepre

Capolona house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$72

Poggio della Bandina - One bedroom apartment

Citta della Pieve apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$154

Ripostena 9

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$1,231

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Housekeeping Included, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$264

Amazing Assisi

Assisi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Housekeeping Included, Swing set or jungle gym, Trampoline

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Price per night from

$436

4 People Apartment

Perugia farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$166

Apartment for 5 People

Perugia farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$197

Agriturismo "Casa al Gianni" - Capanna

Siena apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$135

VILLINO I DUE MORI

La Dogana house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$197

Agriturismo "Casa al Gianni" - Olmo

Siena apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Housekeeping Included, 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, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$160

Ripostena 6-the dryer

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$1,231

Ripostena 10

Casole d'Elsa townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$1,231

Ripostena 11 the barn

Casole d'Elsa apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$1,231

Ripostena-5 The Remittance

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$1,231

Ripostena 7-Trinciatoio

Casole d'Elsa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$1,231

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Swing set or jungle gym, Housekeeping Included, Staffed property, Trampoline

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Price per night from

$377

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Swing set or jungle gym, Housekeeping Included, Staffed property, Trampoline

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Price per night from

$574

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: Housekeeping Included, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$608

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

3 of 4 match: Housekeeping Included, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$1,695

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Housekeeping Included, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$1,614

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Housekeeping Included, Staffed property, Swing set or jungle gym, Trampoline

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Price per night from

$1,354

San Carlo house

Monteleone d'Orvieto villa

  • 10 bedrooms
  • 7 bathrooms
  • sleeps 32

3 of 4 match: Staffed property, Housekeeping Included, Swing set or jungle gym, Trampoline

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Price per night from

$2,149

Po' del Vento:è tutto intorno a te:16, piscina riscaldata, parco giochi, camino

Citta della Pieve guest house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$1,106

Tamarisk House -double in the green - house with 12 beds (3 suites 2 + 2)

Montecastrilli house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 12

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$490

Farmhouse Il Palazzo dei Diavoli Montepulciano - Tuscany Val d 'Orcia

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$148

The green hug

Massa Martana house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$220

Three Arches House

Chiusi apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$122

COTTAGE LA DOLCE AGOGIA

Panicale cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$154

AGRITURISMO ANCONA-IL VILLINO

Saturnia villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$246

Villa Panconesi "Granaio"

Montespertoli apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$95

Antico Borgo Ripostena - 8 Casa Vecchia

Casole d'Elsa apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Trampoline, Housekeeping Included, Staffed property, Swing set or jungle gym

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Price per night from

$1,231

Viewing 38 of 1,212
rentals in Montepulciano

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