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Vacation Rentals & Villas in Montepulciano

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Vacation Rentals & Villas in Montepulciano

About Montepulciano

4,569 Houses

Villa Nobile, Luxury Tuscan Home, Walk to Town

Montepulciano villa

5 bedrooms / 6 bathrooms / sleeps 18

Responds fast! avg. 2 hours 17 minutes

Price per night from

$751

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Very nice home in the historical center

Valiano apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$82

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Charming Apartment in Historic Center of Montepulciano, Tuscany

Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$80

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

Acquaviva di Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 23 minutes

Price per night from

$125

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villa in South Toscany

Montepulciano villa

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 29 minutes

Price per night from

$510

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Tigli #1, two bedrooms apartment close to Montepulciano with Wi-Fi and pool

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Outstanding accommodations!” Tucked away and hard to find. There was a small wooden sign which we missed, but well worth the extra miles we had to drive. The property is well kept and can't beat the views. The apartment we had was a 2br and 2bath and

Price per night from

$133

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Colombi Palace Montepulciano

Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$165

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LA VALIANA Luxury Villa Rental (Montepulciano) - HEATED POOL Incl./ FREE WI-FI

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

Price per night from

$566

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Tigli #6, ground floor flat with one bedroom in Montepulciano area. Wi-Fi & pool

Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

“Wow! A relaxing well appointed holiday home” This is central rural position 6ks from Torrita di Siena makes it easy to enjoy beautiful Tuscany. With easy day trips with a car to Seina, Arezzo, Cortona, Castiglione del Lago or Firenze to name a few.Qu

Price per night from

$93

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Tigli #2, apt Montepulciano area for 5 persons with A/C, Wi-Fi and swimming pool

Montepulciano apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Stunning setting” The apartment complex ( once we found it with a little help!) was stunning and beautifully kept. Unfortunately we had an unseasonably cold week so couldn't make use of the pool and much of the outdoor areas although as our large balc

Price per night from

$133

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Villa Iris - Perfect for families or group of friends

Montepulciano apartment

3 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$195

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5 bedroom Villa in Siena, Tuscany, Italy : ref 5455315

Bivio di San Biagio villa

5 bedrooms / 5 bathrooms / sleeps 9

Price per night from

$591

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Maramai

Abbadia di Montepulciano villa

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 1 hour 15 minutes

Price per night from

$458

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Villa Abbadia

Abbadia di Montepulciano villa

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$316

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Villa Croce

Sant'Albino villa

5 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$373

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

Acquaviva di Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 23 minutes

Price per night from

$91

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Tigli #5, flat near Montepulciano with 2 bedrooms. A/C, Wi-Fi and swimming pool

Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 5

“Stunning estate and perfect location” I went with by partner in June for a 5 night stay after a couple nights in Florence. It was the perfect holiday and this appartment was exactly what we wanted - somewhere quiet, with a pool and close to Tuscan vi

Price per night from

$117

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Maramai

Montepulciano villa

4 bedrooms / 5 bathrooms / sleeps 7

Responds fast! avg. 1 hour 15 minutes

Price per night from

$385

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4 bedrooms in a tower, home of a sculptor

Montepulciano b and b

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 7 minutes

Price per night from

$374

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CasaMontepulciano, In the heart of Montepulciano

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful Montepulciano, Fantastic Host (Luca), Great apartment” We honestly cannot say enough good things about wonderful Luca and his beautiful place in Montepulciano. If you are thinking of staying in this delightful hill town (and it makes a great

Responds fast! avg. 1 hour 4 minutes

Price per night from

$119

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Agriturismo I Fuochi

Valiano farmhouse

11 bedrooms / 9 bathrooms / sleeps 22

Responds fast! avg. 3 hours 16 minutes

Price per night from

$963

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CasaMontepulciano Into the sunset

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 4 minutes

Price per night from

$152

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7 bedroom Villa in Pelago Casanova, Tuscany, Italy : ref 5247920

Sant'Albino villa

7 bedrooms / 7 bathrooms / sleeps 14

Price per night from

$631

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Luxury villa Vignola

Montepulciano villa

7 bedrooms / 8 bathrooms / sleeps 19

Price per night from

$826

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Country House at Antico Podere in Montepulciano, Tuscany

Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$136

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Villa Viole - Dream under the tuscan sun

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$170

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Rustic Stone Brick Villa on Siena Countryside

Montepulciano villa

7 bedrooms / 8 bathrooms / sleeps 16

“Splendid villa and great service!” Amazing place, absolutely fantastic holiday, real Tuscan atmosphere. This is a villa I would recommend to anybody and I hope to see myself visiting it again in the future. Great service and customer assistance by the

Price per night from

$518

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DOWNTOWN WITH A VIEW!Entire Home w. huge Terraces

Montepulciano house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 18 minutes

Price per night from

$175

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6 bedroom Villa in Montepulciano, Tuscany, Italy : ref 5395009

Bivio di San Biagio villa

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$839

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Apartment "Poggino" - Montepulciano

Acquaviva di Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 23 minutes

Price per night from

$102

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Luxury villa Ivory

Sant'Albino villa

8 bedrooms / 9 bathrooms / sleeps 16

Price per night from

$3,109

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Villa Montepulciano

Montepulciano villa

6 bedrooms / 6 bathrooms / sleeps 15

“Perfect...” Perfect Villa and setting to enjoy all the splendors that Tuscany and Montepulciano has to offer. - Rose L., ,

Responds fast! avg. 1 hour 15 minutes

Price per night from

$889

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Tuscan Tower - A unique castle apartment

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Great Place. Quiet town. Beautiful Views” Excellent location. Beautiful apartment. John and Wendy were great to work with. They provided ideas of where to visit and outlined helpful tips for the week we were there. I would highly recommend staying wi

Price per night from

$261

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Rustic Tuscan Farmhouse at Podere Pisinano

Montepulciano villa

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$432

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

Acquaviva di Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 23 minutes

Price per night from

$170

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Tigli #3, 2 bedrooms and 2 bathrooms apt close Montepulciano. Wi-Fi, A/C & pool

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Excellent apartments in a gorgeous location” I stayed with my family and another family for a week in apartments #1 and #3. The couple managing the compound are very nice and helpful, but also very strict and professional about the rules concerning pa

Price per night from

$133

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Villa Manvi 10

Montepulciano villa

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$313

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

Acquaviva di Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 23 minutes

Price per night from

$74

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Viewing 38 of 4,569

About Montepulciano

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Montepulciano is a beautiful village in a hilly area of Tuscany overlooking the Valdichiana countryside. The streets here leave a lasting impression on visitors because of their old world charm and also because of their steep inclines, which can make an adventure out of an ordinary day spent exploring markets and relaxing in cafes.

These sloping streets wind among some unforgettable restaurants and wine cellars. They can also take you to some of the most beautiful renaissance churches in Tuscany. Head beyond the center of town and take a hike through the rolling countryside of world famous vineyards and olive groves. At the end of the day, head back to experience the delicious cuisine that brings knowledgeable foodies to Montepulciano from all over the world and enjoy a glass of vino nobile as the sun sets.

Here are a few additional suggestions as you plan your trip:

  • Visit the Chiesa di San Biagio: This domed renaissance church with its fantastic marble alter piece lies in a valley just to the west of the Chiesa del Gesu, another impressive work of religious architecture.
  • Explore the Museo Civico: The town of Montepulciano has its own civic museum, which houses artifacts documenting its long history.
  • Explore the cantinas of Montepulciano: Tuscany is known for its wine, but Montepulciano in particular has a charming community of cantinas that offer tours through cellars packed with casks followed by a unique tasting experience.
  • Take a tour of the Azienda Agricola Canneto: This sprawling vineyard close to the Church of San Biagio produces regional vino nobile and extra virgin olive oil. Come to tour the grounds and learn more about how these precious items are produced.
  • Take an Italian cooking class: Sample the unforgettable flavors of Tuscany at the restaurants and trattorias of Montepulciano, then take a course from a skilled chef and learn how to bring these flavors home with you.
  • Visit the Formaggi Cugusi Silvana: The family that runs this artisanal pecorino cheese shop makes cheese with the milk from their own sheep that graze in the pastures of the Val d'Orcia.

You'll have no trouble finding world class dining opportunities, and you'll also have no trouble finding a vacation rental that offers luxurious views of the Tuscan countryside. Find an elegant condo downtown or a beautiful rustic villa overlooking the vineyards. While you're visiting Montepulciano, you may want to include a day trip to the beautiful town of Torrita di Siena in your plans.

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