Vacation Rentals & Villas in Montepulciano

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103 Houses

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Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

Match: Swing set or jungle gym Wheelchair accessible

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Price per night from

$1,358

Match: Swing set or jungle gym Wheelchair accessible

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Price per night from

$3,085

villa ai cedri

Cortona villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swing set or jungle gym Wheelchair accessible

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Price per night from

$406

Source Val'd'Orcia Sienese farmhouse with pool and air conditioning

Monticchiello apartment

  • 3 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Swing set or jungle gym Wheelchair accessible

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Price per night from

$840

Superior Apartment

Castiglione del Lago b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

Match: Swing set or jungle gym Wheelchair accessible

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Price per night from

$104

Three Arches House

Chiusi apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Swing set or jungle gym Wheelchair accessible

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Price per night from

$123

Poggio della Bandina - One bedroom apartment

Citta della Pieve apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swing set or jungle gym Wheelchair accessible

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Price per night from

$155

Villa Monarca -Tuscany-

Torrita di Siena villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

Match: Swing set or jungle gym Wheelchair accessible

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Price per night from

$1,481

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Apartments in Residence

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

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Farm Humile - Suite "Solevante"

Chianciano Terme b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$222

Borgo Sanguineto - Historic tower with lake view, garden and swimming pool

Tuoro sul Trasimeno tower

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$87

Villa Antico Casale - Entire property exclusive 14 beds

Panicale villa

  • 14 bedrooms
  • 4 bathrooms
  • sleeps 14

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$679

Typical Umbrian villa, pool, relaxation and views

Castiglione del Lago villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 16

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$441

Casa di roberto

Siena b&b

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$68

House with private swimming pool and panoramic lake view

Tuoro sul Trasimeno house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

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Price per night from

$203

Poggio Etrusco: Tuscan B&B, apts, & Cooking School

Montepulciano villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

“Beyond adjectives” There is no way to describe our stay here! Pamela and Johnny were more than welcoming. We arrived with our 7 & 4 year olds in tow...and from The gate greeting, we felt as if we were at "memee's house". Each kid had a job...gate keeping and keeping track of the red fetch toy for Bella. We had an unwarranted snafu on credit card deposits in Rome the day before...but it was of no concern to these wonderful and true hosts... Each morning, The breakfast was true to Tuscany yet appealing to the kids... we were within an hours drive of each of our potential destinations...and each evening with a game of fetch watching Bella and the kids...the hosts helped us decide upon on the next days itinerary! We will be back with the whole family in July!

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$1,049

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$167

Villa PoliFlora GARDEN

Monticchiello apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$99

Casale Fontocchio with nice swimming pool

Cortona villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$396

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

Cortona apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$438

La Graziosa, graceful cottage with lovely pool.

Cortona villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Quiet beautiful place” We had an excellent holiday in this place. We will surely come back !

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$141

Masseria del Bosco - Appartamento IL GRANAIO - Podere Palazzone

Chianciano Terme apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$253

Sunflower

Lucignano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair accessible, Swing set or jungle gym

1 of 2 filters match

Price per night from

$81

Family Room

Castiglione del Lago apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Wheelchair accessible, Swing set or jungle gym

1 of 2 filters match

Price per night from

$99

Farmhouse

Pienza house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair accessible, Swing set or jungle gym

1 of 2 filters match

Price per night from

$124

Agriturismo La Giuiaia - Appartamento Pietravolta

Citta della Pieve apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$99

Agriturismo il Poggio di Cantagallina

Castiglione del Lago apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$111

Holiday Resort in Montepulciano T,air conditioning,swimmingpool,wine tasting

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 2 hours 58 minutes

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$204

Tignanello: Tuscan Style home for wine lovers - a Fontanaro Property

Paciano farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$358

«Monastero San Silvestro-Historic Farmhouse

Cortona finca

  • 15 bedrooms
  • 10 bathrooms
  • sleeps 30

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$2,407

Agriturismo Tenuta Il Polardo

Piegaro townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$104

Villa ulivi & La Casina

Lucignano villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$662

Small farm in Crete Senesi

Montisi farmhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

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Country House at Antico Podere in Montepulciano, Tuscany

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$148

contryhouse near siena: Apartment 2 Person

Sinalunga apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$457

“Excellent villa in a beautiful location” We were three families holidaying in this wonderful villa with our children, ages 9-16. The kids loved the pool and us adults enjoyed soaking up the Umbrian sun in the well-maintained gardens. We explored the local area-Montepulciano, Isla Maggiore and Castiglione del Lago (market Wednesday am). We also did Siena on the train. Would have liked to have done more,but a week is not enough. Katia was such a welcoming host,nothing was too much trouble. Thank you very much Katia, hope to see you in a year or two!

Responds fast! avg. 2 hours 8 minutes

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$617

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!

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$371

Charming Cottage in Peaceful Country Setting - Sleeps 6

Gracciano cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Wheelchair accessible

1 of 2 filters match

Price per night from

$235

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rentals in Montepulciano

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