Vacation Rentals & Villas in Montepulciano

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1,294 Houses

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Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Private outdoor pool (heated) Safe Staffed property

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Price per night from

$741

Match: Private outdoor pool (heated) Safe Staffed property

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Price per night from

$1,839

Villa Castellare de Sernigi stunning sunsets for 13/14 people

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

Match: Private outdoor pool (heated) Safe Staffed property

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Price per night from

$2,115

Villa Rovicciano, sleeps 16+4. Family reunions, cooking service, heatable pool

Castel Ritaldi villa

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 20

Match: Private outdoor pool (heated) Safe Staffed property

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Price per night from

$1,481

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 20

Match: Private outdoor pool (heated) Safe Staffed property

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Price per night from

$346

Suite CielAzzurro

Arezzo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Private outdoor pool (heated) Safe Staffed property

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Price per night from

$74

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Agriturismo Incrociata Arco

Pietraviva farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$195

Agriturismo Incrociata Cantina

Pietraviva farmhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$195

Agriturismo Incrociata Colombaio

Pietraviva farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$195

B & B THE OLD Lieutenancy SUITE TRIPLE

Citta della Pieve b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 13 minutes

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$99

Palazzo di Valli

Siena villa

  • 11 bedrooms
  • 11 bathrooms
  • sleeps 24

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$1,588

The Countess' Blue Suite

Montepulciano guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$198

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

Cavriglia farmhouse

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 15

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

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Price per night from

$605

2 MINI APPARTAMENTI ELEGANTI INDIPENDENTI CON PARCHEGGIO

San Martino in Colle house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$81

Tus003 - Villa surrounded by rolling hills, Tuscany

Contignano condo

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 18

2 of 3 match: Staffed property, Private outdoor pool (heated), Safe

2 of 3 filters match

Price per night from

$2,727

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

2 of 3 match: Safe, Private outdoor pool (heated), Staffed property

2 of 3 filters match

Price per night from

$1,111

2 of 3 match: Staffed property, Private outdoor pool (heated), Safe

2 of 3 filters match

Price per night from

$1,298

Locanda di Artemide , eleganza e autenticità

Montebuono apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$209

FARM-HOUSE "PODERE OUTLETS" (APARTMENT "B")

Castel Del Piano house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$50

Bed & Breakfast Il Paradiso

Capolona b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$87

Bed and Breakfast Paradise-The Tabaccaia

Capolona apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$130

B & B Il Paradiso - La Cantinetta

Capolona barn

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$87

La Locanda di Artemide, elegante camera per due

Sorano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$104

Villa Serena

Gubbio apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

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Lake, countryside, relaxation and healthy food

Magione apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

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Borgo di Mezzo

Castelnuovo dell'Abate apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 49 minutes

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$111

Apartment 3 Stiozzi Palace Ridolfi Certaldo Alto

Certaldo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$98

La Scuderia Casa Vacanze

Arezzo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$198

B&b baldovino di Monte San Savino

Monte San Savino b&b

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$87

Farm Humile - Suite "Solevante"

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$223

Soarzio apartment with pool near San Gimignano 4

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$124

Casa Falcucci

Gubbio house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$110

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$186

Podere il Pino 5 - Apartment with private garden and shared swimming pool

Poggibonsi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$173

Agriturismo Humile - Suite "Lunaspicchio"

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$223

Farm Humile - Agriculture and Hospitality B & B

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$223

Podere il Pino 7 - Apartment with private terrace and shared swimming pool

Poggibonsi apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$161

Podere il Pino 8 - 2 bedroom apartment with private garden and shared pool

Poggibonsi apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (heated), Safe, Staffed property

2 of 3 filters match

Price per night from

$210

Viewing 38 of 1,294
rentals in Montepulciano

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