Vacation Rentals & Villas in Montepulciano

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2,474 Houses

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

Match: Stereo system Private outdoor pool (unheated) Staffed property Trampoline

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Price per night from

$1,607

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Canonici

Montecastrilli villa

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 11

3 of 4 match: Staffed property, Stereo system, Private outdoor pool (unheated), Trampoline

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Casale panoramicissimo con piscina S. Damiano

Todi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Stereo system, Private outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$110

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

Chianciano Terme villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 22

3 of 4 match: Staffed property, Stereo system, Private outdoor pool (unheated), Trampoline

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Price per night from

$699

Amazing Assisi

Assisi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Stereo system, Private outdoor pool (unheated), Trampoline

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Price per night from

$434

Loggiato apartment - Podere Casarotta

Loro Ciuffenna apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

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Price per night from

$106

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Stereo system, Private outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$1,345

Tuscany Villa Bagnoro Arezzo Country House

Arezzo villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

3 of 4 match: Stereo system, Private outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$1,223

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

Castiglion Fiorentino villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 15

3 of 4 match: Stereo system, Private outdoor pool (unheated), Staffed property, Trampoline

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Price per night from

$489

Comfort under the Umbrian Sun! Pool and Air Conditioned!!

Spoleto villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Stereo system, Private outdoor pool (unheated), Trampoline

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Price per night from

$453

Villa ai Cedri

Pergo farmhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Stereo system, Private outdoor pool (unheated), Trampoline

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Price per night from

$403

Villa Borgo Taverne

Corciano villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

3 of 4 match: Staffed property, Stereo system, Private outdoor pool (unheated), Trampoline

3 of 4 filters match

Price per night from

$699

Borgo Valecchie, Exclusive Villa set with private pool, Cortona, Tuscany

Montanare villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Stereo system, Private outdoor pool (unheated), Trampoline

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Price per night from

$551

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, Stereo system, Private outdoor pool (unheated), Trampoline

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Price per night from

$123

Casale Aiaccia

Arezzo farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Staffed property, Stereo system, Private outdoor pool (unheated), Trampoline

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Price per night from

$251

Villa Casolare

Perugia villa

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 14

3 of 4 match: Staffed property, Stereo system, Private outdoor pool (unheated), Trampoline

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Price per night from

$612

Poggerina luxury private villa with stunning view

Greve in Chianti villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Beautiful location and villa, gracious and helpful hosts” I researched extensively before choosing this villa and it more than met our expectations. From the first email Emanuele and his family provided excellent service and were accessible and helpful. Moreover, they made us feel like more than paying guests, more like friends. The villa itself was very spacious and roomy, with a kitchen that had everything we needed. The views are spectacular, and it's quiet and peaceful. I would recommend doing both the pizza night and the cooking night. Both were excellent. Our stay couldn't have been any better. We would highly recommend this villa.

Responds fast! avg. 3 hours 16 minutes

3 of 4 match: Staffed property, Stereo system, Private outdoor pool (unheated), Trampoline

3 of 4 filters match

Price per night from

$612

San Carlo house

Monteleone d'Orvieto villa

  • 10 bedrooms
  • 7 bathrooms
  • sleeps 32

3 of 4 match: Staffed property, Stereo system, Private outdoor pool (unheated), Trampoline

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Price per night from

$2,140

Private Villa with a wonderful view and private pool, close to Siena

Siena villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

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Price per night from

$441

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, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$488

Cungi, Villa with private pool

Sansepolcro villa

  • 13 bedrooms
  • 12 bathrooms
  • sleeps 30

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$1,101

LA PIEVE - Casale charming

Colle di Val d'Elsa farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$263

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$612

Porciglia Alta, luxury country house located in the heart of the Chianti region

Greve in Chianti house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$445

Gelso apartment - Podere Casarotta

Loro Ciuffenna apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$97

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

3 of 4 match: Stereo system, Private outdoor pool (unheated), Staffed property, Trampoline

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comfortable room by andrea

Cortona house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Private outdoor pool (unheated), Trampoline, Stereo system, Staffed property

2 of 4 filters match

Price per night from

$62

Tipical rural cottage in Tuscany hills

Scansano cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 4 match: Staffed property, Private outdoor pool (unheated), Stereo system, Trampoline

2 of 4 filters match

Price per night from

$74

Poggio Rosemary - luxury farmhouse

Montespertoli farmhouse

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 8

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$1,223

ART-HANGAR BY TUSCAN-EXPERIENCE

Montalcino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$710

Petrolo winery Villa. Events, weddings & large families. Service included

San Leolino villa

  • 16 bedrooms
  • 14 bathrooms
  • sleeps 33

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$1,957

Villa Fada

Todi villa

  • 6 bedrooms
  • 9 bathrooms
  • sleeps 10

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$734

Villa Petrea

Bucine villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 20

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$1,468

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, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$282

Orchidea - Two double bedroom # 6

Val di Chiana guest house

  • 13 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$269

Villa Castellare de Sernigi stunning sunsets for 13/14 people

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$2,096

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

3 of 4 filters match

Price per night from

$159

Tuscany villa, private pool, for family & group

Mercatale di Cortona farmhouse

  • 12 bedrooms
  • 8 bathrooms
  • sleeps 24

3 of 4 match: Trampoline, Stereo system, Private outdoor pool (unheated), Staffed property

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Viewing 38 of 2,474
rentals in Montepulciano

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