Vacation Rentals & Villas in Montepulicano

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253 Houses

B&B Il Pozzo - Giuggiolo

Sinalunga b&b

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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$62

Romantic farm for 2/4 persons with pool near Siena

Trequanda villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$111

Apartment "The Hague" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$209

Villa LA VALIANA (Montepulciano)

Montepulciano villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Paradise in Tuscany!” This lovely villa has it all and is the kind of place that makes you want to stay and 'while away' the afternoon among its many outdoor spaces: whether it's dining in the gazebo overlooking the vineyard, watching as the evening sun sets over the gently rolling hills, relaxing in a chaise by the glistening pool, enjoying a café crème or glass of wine on the patio surrounded by roses, lemon trees and pots of flowers, or gazing beyond at Cortona high on a hill or Trasimeno Lake in the valley below, you will come to know this is a very special place. La Valiana is centrally located for explorations to nearby villages and wineries, Cortona, lovely Pienza (a favorite), Montepulciano or easy day trips to Montalcino, Orvieto, Siena, Arezzo, Florence, Chianti and beyond. It is comfortable and beautifully decorated in classic, Tuscan style with fine architectural details such as wrought iron arched windows, doors and Travertine marble floors. You will be well taken care of and looked after by Cecelia and her Family who are the most gracious hosts - they are dedicated to making your stay a wonderful, memorable one, making themselves available should you need any assistance. Their warm hospitality and attention to detail will make you feel special and, at once, a part of the family. If you opt to have a meal prepared and waiting for your arrival after a long day of travel or touring, it will not disappoint and, quite possibly, could be one of the best meals in all of Tuscany, especially when enjoyed under the stars. You will want for nothing - except perhaps to extend your stay, or at the very least, come back again! You can be sure we will be back!!

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$741

Apartment "Belvedere" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$172

Podere Osteria

Pienza apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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$309

Villa Oliveto

Castelmuzio villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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$672

Tuscan Tower - A unique castle apartment

Montefollonico apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

“Heaven on earth!” This castle apartment, this town and this region of Tuscany were absolutely beautiful, exceeding our expectations! We were 2 couples celebrating our 25th anniversary,and stayed here following our 12 day Mediterranean cruise last October (2012). We had seen amazing countries and places on our cruise, however when we arrived here and climbed the stairs to the tower in the apartment, the view took our "breath away"! This was the highlight of our entire trip! This was the first time we had rented an apartment, and of course a little nervous about the process. Without meeting John and Wendy, they made us feel so comfortable and welcome. The "Welcome Package" that they provide gives you all the information that you need for your stay and any question you may have, you are sure to find the answer in their guide. Located in this amazing medieval town of Montefollonico, you are in the heart of the most beautiful area of Tuscany. John and Wendy include the sights to see and places to visit in their guide, which we followed and were so glad we did! The town provides everything you need, all within a short walking distance - groceries (including wine, spirits and beer) and local restaurants which were all very good. The apartment was perfect for 2 couples,we each had our own bedroom and own bathroom. The beds were very comfortable and all the linens and towels provided were of the highest standard. Just remember no elevators here, so when you first arrive, you must carry your bags up the stairs. John and Wendy let us know that the internet was a little unstable, which it was, but that was okay too. Every daylight moment we spent at the apartment were spent in the tower, enjoying our Tuscany wines, along with our sheep cheese( so good Wendy!) and never getting enough of the beautiful views, the peace all around us, and the sounds of the birds singing. Truly heaven on earth! Thank you John and Wendy for sharing your world with us!

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$229

DOWNTOWN WITH A VIEW!Entire Home w. huge Terraces

Montepulciano house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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$281

Casa Oliveto

Castelmuzio house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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$705

"Policiano Suite" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$309

Apartment "Poggino" - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$186

Casale Etruria

Chianciano Terme house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$353

L'ANTICO GRANAIO

Montepulciano cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$153

Villa Camelia

Farneta house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$235

Studio "Rustic" at The House of the Oaks - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$129

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$184

ART-HANGAR BY TUSCAN-EXPERIENCE

Montalcino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$716

Apartment "Pratino" - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$172

Villa La Bifora

Sinalunga villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

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$778

Podere Monti, 7 bedrooms villa near Montepulciano. Private pool, A/C and Wi-Fi!

Sant'Albino villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 21

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$803

The Molinaccio 3

Montepulciano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$556

Studio "Borghetto" at The House of the Oaks - Montepulciano

Montepulciano studio

  • Studio
  • 1 bathroom
  • sleeps 2

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$129

La Dimora Main Villa + 1 Cottage for 18

Sarteano villa

  • 8 bedrooms
  • 1 bathroom
  • sleeps 18

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$3,157

La Dimora Main Villa + 2 Cottages for 20

Sarteano villa

  • 9 bedrooms
  • 2 bathrooms
  • sleeps 20

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Price per night from

$3,518

Aiola

Sarteano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 12

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$1,663

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Price per night from

$911

The Molinaccio 7

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

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Price per night from

$1,111

Belguardo BELGUARD 1

Chianciano Terme apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

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$338

Belguardo BELGUARDO 2

Chianciano Terme house

  • 11 bedrooms
  • 3 bathrooms
  • sleeps 8

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$506

Il Sasso Il Sasso

Chianciano Terme house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

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$1,155

La Valle Valley

Chianciano Terme house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$824

Tenuta Senese Tenuta Senese

Montepulciano house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$646

Villino Cortona - Casa vacanze con piscina privata, wifi, Ac - Toscana

Montecchio villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$162

The Source The Source

Chianciano Terme apartment

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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$747

La Dimora Main Villa for 14 adults plus 2 children

Sarteano villa

  • 7 bedrooms
  • 11 bathrooms
  • sleeps 16

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Price per night from

$2,787

Romantica

Pienza villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 7 minutes

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Price per night from

$1,123

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Price per night from

$291

Viewing 38 of 253
rentals in Montepulicano

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