Vacation Rentals & Villas in Montepulciano

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1,792 Houses

Villa Nobile, Luxury Tuscan Home, Walk to Town

Montepulciano villa

5 bedrooms / 6 bathrooms / sleeps 18

Responds fast! avg. 1 hour 50 minutes

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$1,193

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

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Price per night from

$149

Colombi Palace Montepulciano

Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 4

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$180

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

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 6

“family reunion” we looked for a place where the whole family could celebrate a 70'years birthday. We were altogether 4 families of 8 adults and 7 children. The property was ideal for us. We occupied 5 apartments and had the whole place at our disposal. It was nice that we had the whole property at our own so that we should not consider other residents. All apartments were in good standard and the pool area was nice. We had really no complains at all. One evening a pizza evening was arranged by the manager and it was splendid. Further the surrounding towns were interesting and marvelous.

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$128

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.Quiet, comfortable with a very suitable kitchen facilities, all helping to make a very relaxing home base in the middle of the wine area. A good map and GPS navigation system is a must to find your way in this amazing countryside.

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$91

Charming Apartment in Historic Center of Montepulciano, Tuscany

Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 27 minutes

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$87

4 bedrooms in a tower, home of a sculptor

Montepulciano b&b

4 bedrooms / 4 bathrooms / sleeps 8

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$409

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

Montepulciano apartment

3 bedrooms / 2 bathrooms / sleeps 6

“Wonderful place with beautiful vistas of the hills and valley fr” We were able to stay 5 days and 4 nights in this lovely place. The property was as or better than described. Very comfortable and clean. Everything we needed for the time we stayed there. It was a very nice location to be able to take day trips to Siena, Pienza, Montepulciano, Montalcino and Orvieto on the way back to Rome. Such great views from apt #2. We even saw deer in the evening and morning running through the fields below. Montepulciano is very close and you can be there in a matter of a few minutes to shop at the Conard or enjoy shopping and meals. There are a lot of rules on lists provided to follow regarding trash, cleaning, linens, etc. We didn't see much of the caretakers as they had other jobs/work, a new baby, etc. But they were very pleasant and helpful if we needed anything. This is definitely a place we would go back to again.Once we found it. I am glad we got to the location during the day and not at night. You just really have to believe the directions and keep going. The signs are a bit small and I am glad everyone was looking for them. Please go eat at the 13 Gobbi in Montefollonico about 5-6 miles away on a hill top to the north. You will love it. And have their house wine, great. By the way, a bottle of wine and olive oil was provided upon our stay. Both were very good. Wish I could have bought more of it.

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$128

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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$566

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

Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 5

“Return visit” One again we enjoyed our visit to this well run set of apartments. They are ready on time, cleean and well equiped. A caretaker lives on site to provide backiup if needed. The gardena and pool are tell tended and maintained. Montipulciano is 10 mins away by car. Be aware that it is in the middle of the countryside with no shops or restaurants nearby.

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Price per night from

$112

Agriturismo I Fuochi

Valiano farmhouse

11 bedrooms / 9 bathrooms / sleeps 22

Responds fast! avg. 2 hours 45 minutes

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Price per night from

$1,053

Villa Iris - Perfect for families or group of friends

Montepulciano apartment

3 bedrooms / 3 bathrooms / sleeps 5

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$213

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

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Price per night from

$112

Villa Viole - Dream under the tuscan sun

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$186

CasaMontepulciano Into the sunset

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 4

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$166

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 base for touring Tuscany and Umbria), you will not regret your experience staying at Luca's apartment. Our story: My husband, adult son and I stayed in Luca's apartment for a week in March (2014). From the time I contacted Luca (in February? January?) until the moment we left Montepulciano, he was kind, full of information and sooo easy to deal with. He has a lovely good nature that is contagious! He took time to tell us about towns to visit, restaurants we should consider and just generally about the area around Montepulciano that he so obviously loves. And his apartment was simply perfect! A master bedroom (very comfortable big bed) and full bathroom for my husband and I and a separate full bathroom for our son. The open kitchen/living room was ideal with its windowns overlooking the winding roads and ancient buildings of this historic village. The apartment was completely updated yet still had the "feel" of an older place. Great showers and wi-fi too! We absolutely loved it! We have already told half of Portland, Oregon (that's an obvious exageration!) about Luca and his magical apartment! Don't hesitate to rent his place - you will be forever glad that you did. And you will end up having a fantastic Italian friend named Luca. We will be back, Luca!

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Price per night from

$130

Country House at Antico Podere in Montepulciano, Tuscany

Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

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$149

DOWNTOWN WITH A VIEW!Entire Home w. huge Terraces

Montepulciano house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 45 minutes

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$247

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 payment, signing the lease agreement, etc. Expect to do a lot of paperwork and sign away all your rights to anything at all as part of the check-in process. But once that is done, they do their best to make your stay comfortable and pleasant. The good: the apartments are spacious and extremely well equipped, very comfortable. We were able to cook lunches and dinners for 9 people in the kitchen of our apartment (#1), comfortably; and we also were able to fit ourselves around both the indoor table and the outdoor patio table. There is a dishwasher and washing machine in each apartment, which is great. The bad: in aug. 2011, at least, internet by wifi was shaky at best, and in general almost impossible in #1. In #3 it was better. The problem is that the setup had a central wifi router someplace in the compound, and then repeater/extender routers in each apartment; but the thick stone walls of the buildings makes the connection weak and unreliable. Since you pay extra for the wifi, it's extra annoying when it doesn't work. Perhaps the owners have fixed this by now. The ugly: As far as I can tell, nothing in the Montepulciano region is ugly. The surroundings could hardly be more beautiful and perfect for a relaxing summer holiday.

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$128

Apartment "Poggino" - Montepulciano

Acquaviva di Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 23 minutes

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$124

5 bedroom Tuscan villa with pool

Montepulciano house

5 bedrooms / 4 bathrooms / sleeps 10

“fantastic, beautiful villa” 10 of us stayed here for my wedding and there was nothing we could find fault with. The bedrooms were all spacious. Lovely en suite to the master bedroom.kitchen had all the mod cons required whilst keeping a tuscan charm. Gardens beautiful and set i tbd beautiful tuscan countryside. Ideal location. Will definately be back.

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$322

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

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$87

"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

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$200

Room in a tower between Cortona and Montepulciano

Montepulciano b&b

1 bedroom / 1 bathroom / sleeps 2

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$112

Beautiful apartment with pool in Montepulciano

Valiano apartment

3 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 45 minutes

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Price per night from

$211

L'ANTICO GRANAIO

Montepulciano cottage

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$154

Ostro Bed & Breakfast at Montepulciano in Tuscany

Montepulciano b&b

2 bedrooms / 3 bathrooms / sleeps 4

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$124

Borgo dei Sette Tigli #4

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect!” We had a 4-night stay here in early July of this year and had such a wonderful experience. We were greeted by alice who was very accommodating and patient even though we lost our way and were an hour late arriving. She was a sweet as can be and made sure we were settled and had all our questions answered before leaving. Barbara (the owner, I believe) came by the next day to greet us and was also wonderful, making sure that we were satisfied. She was taking care of details regarding her forthcoming nuptials which were to take place 5 days after our arrival. She was very accommodating and helpful even though she must have had lots on her mind. We rented a 2-bedroom, 2-bathroom apartment with a fully-equipped kitchen, living room/dining room, small walkout with table and chairs off of the kitchen. This was perfect for our family of 4 -- two adults and two teenage girls. The accommodations are superb: comfortable beds with great quality linens; recently and tastefully renovated rooms, spacious and inviting, fully equipped kitchen with dish washer and clothes washer; clothes are a quick dry in the summer sun on a dryer rack that is provided. The exterior of the buildings are very attractive, landscaping is detailed and well tended and there is a beautiful, beautiful pool. Now picture this in the middle of the lovely landscape of the Tuscany region. Need I say more? If you're thinking of staying here, don't hesitate, it is superb. Ideally located close to Montepulciano (5 minutes by car) and not far from the major highway (15 minutes tops) if you feel that you'll be doing some day trips. Exceptional value for the money. I highly recommend this vacation rental and only wish I could go back. Hopefully some day.

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$130

Holiday home casa Ciliano

Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 5

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$106

Apartment Il Ciliegio

Valiano apartment

2 bedrooms / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 45 minutes

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$163

Apartment "Pratino" - Montepulciano

Acquaviva di Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 23 minutes

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Price per night from

$113

Podere Monti

Sant'Albino villa

7 bedrooms / 8 bathrooms / sleeps 21

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Price per night from

$566

Le Manzinaie - Glicine - Romantic apartment in Tuscany

Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

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$118

The Molinaccio 7

Montepulciano villa

7 bedrooms / 8 bathrooms / sleeps 16

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$991

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

Montepulciano studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 23 minutes

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$87

Villa Calabresi: 3 bedroom villa in Montepulciano

Montepulciano house

3 bedrooms / 2 bathrooms / sleeps 6

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$515

The Molinaccio 3

Montepulciano villa

3 bedrooms / 3 bathrooms / sleeps 6

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$464

Villa Cypress Villa Cypress, Tuscany, Tuscan villa, Montepulciano, Siena,

Montepulciano house

6 bedrooms / 7 bathrooms / sleeps 12

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Price per night from

$1,029

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