Vacation Rentals & Villas in Montepulciano

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238 Houses

La Dimora Main Villa + 1 Cottage for 18

Sarteano villa

  • 8 bedrooms
  • 1 bathroom
  • sleeps 18

Match: Safe Staffed property Wheelchair accessible

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Price per night from

$3,158

La Dimora Main Villa + 2 Cottages for 20

Sarteano villa

  • 9 bedrooms
  • 2 bathrooms
  • sleeps 20

Match: Safe Staffed property Wheelchair accessible

All filters match

Price per night from

$3,519

La Dimora Main Villa for 14 adults plus 2 children

Sarteano villa

  • 7 bedrooms
  • 11 bathrooms
  • sleeps 16

Match: Safe Staffed property Wheelchair accessible

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Price per night from

$2,788

Three Arches House

Chiusi apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Safe Staffed property Wheelchair accessible

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Price per night from

$123

Farm Humile - Suite "Solevante"

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Safe Staffed property Wheelchair accessible

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Price per night from

$222

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Poggio della Bandina - One bedroom apartment

Citta della Pieve apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Safe, Staffed property, Wheelchair accessible

2 of 3 filters match

Price per night from

$155

Superior Apartment

Castiglione del Lago b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

2 of 3 match: Safe, Staffed property, Wheelchair accessible

2 of 3 filters match

Price per night from

$104

Agriturismo La Giuiaia - Appartamento Pietravolta

Citta della Pieve apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Safe, Staffed property, Wheelchair accessible

2 of 3 filters match

Price per night from

$99

La Sosta di Braccio - casa vacanze

Macchie guest house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 4

2 of 3 match: Safe, Staffed property, Wheelchair accessible

2 of 3 filters match

Price per night from

$99

2 of 3 match: Staffed property, Safe, Wheelchair accessible

2 of 3 filters match

Price per night from

$167

Agriturismo il Poggio di Cantagallina

Castiglione del Lago apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Safe, Staffed property, Wheelchair accessible

2 of 3 filters match

Price per night from

$111

«Monastero San Silvestro-Historic Farmhouse

Cortona finca

  • 15 bedrooms
  • 10 bathrooms
  • sleeps 30

2 of 3 match: Safe, Staffed property, Wheelchair accessible

2 of 3 filters match

Price per night from

$2,407

il Nido L'Antica Vetreria

Piegaro apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Safe, Staffed property, Wheelchair accessible

2 of 3 filters match

Price per night from

$124

La Terrazza L'Antica Vetreria

Piegaro apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Safe, Staffed property, Wheelchair accessible

2 of 3 filters match

Price per night from

$150

House with private swimming pool and panoramic lake view

Tuoro sul Trasimeno house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

2 of 3 match: Staffed property, Safe, Wheelchair accessible

2 of 3 filters match

Price per night from

$203

Tuscany villa, private pool, for family & group

Mercatale di Cortona farmhouse

  • 12 bedrooms
  • 8 bathrooms
  • sleeps 24

2 of 3 match: Safe, Staffed property, Wheelchair accessible

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Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

2 of 3 match: Safe, Staffed property, Wheelchair accessible

2 of 3 filters match

Price per night from

$1,358

2 Bedroom, 2 bathroom, Quiet , Elegant Villa with pool - sleeps 4 + 2

Cortona apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Staffed property, Safe, Wheelchair accessible

2 of 3 filters match

Price per night from

$439

Wonderful and romantic Tuscany

Foiano Della Chiana villa

  • 12 bedrooms
  • 8 bathrooms
  • sleeps 30

2 of 3 match: Safe, Staffed property, Wheelchair accessible

2 of 3 filters match

Price per night from

$864

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: Wheelchair accessible, Safe, Staffed property

2 of 3 filters match

Price per night from

$99

The Countess' Blue Suite

Montepulciano guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 3 match: Wheelchair accessible, Safe, Staffed property

2 of 3 filters match

Price per night from

$198

Vacatoin Rentals at Le Celle Del Farinaio in Short

Cortona villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

“Charming house with a beautiful garden” Le Celle lies on the hillside, secluded and peaceful. The house is of high standard and keeps cool during the hot season. The garden is amazing, full of so many different flowers, plants and trees. The Tarquini family are friendly and helpful, and we did not miss anything during our stay!

2 of 3 match: Staffed property, Safe, Wheelchair accessible

2 of 3 filters match

Price per night from

$371

2 of 3 match: Safe, Staffed property, Wheelchair accessible

2 of 3 filters match

Price per night from

$3,085

villa ai cedri

Cortona villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Staffed property, Safe, Wheelchair accessible

2 of 3 filters match

Price per night from

$406

Agriturismo Humile - Suite "Lunaspicchio"

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

2 of 3 match: Wheelchair accessible, 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: Wheelchair accessible, Safe, Staffed property

2 of 3 filters match

Price per night from

$223

Le Palazze, country b&b

Citta della Pieve b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 30 minutes

2 of 3 match: Wheelchair accessible, Safe, Staffed property

2 of 3 filters match

Price per night from

$186

B & B THE OLD Lieutenancy APARTMENT LA ROCCA

Citta della Pieve b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 13 minutes

2 of 3 match: Wheelchair accessible, Safe, Staffed property

2 of 3 filters match

Price per night from

$223

2 of 3 match: Wheelchair accessible, Safe, Staffed property

2 of 3 filters match

Price per night from

$926

Podere Le Cantine

Lucignano farmhouse

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 28

2 of 3 match: Wheelchair accessible, Safe, Staffed property

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Price per night from

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Limonaia Apartment

Sinalunga apartment

  • 1 bedroom
  • 10 bathrooms
  • sleeps 2

2 of 3 match: Wheelchair accessible, Safe, Staffed property

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Price per night from

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Arcs apartment

Sinalunga apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Wheelchair accessible, Safe, Staffed property

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Price per night from

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X Apartment

Sinalunga apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Wheelchair accessible, Safe, Staffed property

2 of 3 filters match

Price per night from

$247

Stonehouse Valdorcia Tuscany

Montefollonico condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Wheelchair accessible, Safe, Staffed property

2 of 3 filters match

Price per night from

$210

Il Loggiato, two bedrooms apartment in the Crete Senesi region. Pool, A/C, Wi-Fi

Rapolano Terme apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 3 match: Wheelchair accessible, Safe, Staffed property

2 of 3 filters match

Price per night from

$278

La Corte, one bedroom apt on the ground floor close Asciano. Pool, A/C & Wi-Fi

Rapolano Terme apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Wheelchair accessible, Safe, Staffed property

2 of 3 filters match

Price per night from

$149

Il Forno, unique apartment for 5 pax in the Crete Senesi area. Pool, A/C & Wi-Fi

Rapolano Terme apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Wheelchair accessible, Safe, Staffed property

2 of 3 filters match

Price per night from

$309

COTTAGE LA DOLCE AGOGIA

Panicale cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Wheelchair accessible, Safe, Staffed property

2 of 3 filters match

Price per night from

$155

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rentals in Montepulciano

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