Vacation Rentals & Villas in Montepulciano

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3,898 Houses

Villa Nobile, Luxury Tuscan Home, Walk to Town

Montepulciano villa

5 bedrooms / 6 bathrooms / sleeps 18

Responds fast! avg. 1 hour 50 minutes

Price per night from

$859

Very nice home in the historical center

Valiano apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$98

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 14 minutes

Price per night from

$149

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!!

Price per night from

$565

Colombi Palace Montepulciano

Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$179

Charming Apartment in Historic Center of Montepulciano, Tuscany

Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 0 minutes

Price per night from

$86

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.

Price per night from

$127

Villa Iris - Perfect for families or group of friends

Montepulciano apartment

3 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$212

4 bedrooms in a tower, home of a sculptor

Montepulciano b&b

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$408

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.

Price per night from

$89

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.

Price per night from

$128

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

Acquaviva di Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 14 minutes

Price per night from

$111

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!

Responds fast! avg. 3 hours 51 minutes

Price per night from

$129

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.

Price per night from

$111

Agriturismo I Fuochi

Valiano farmhouse

11 bedrooms / 9 bathrooms / sleeps 22

Responds fast! avg. 2 hours 45 minutes

Price per night from

$1,045

CasaMontepulciano Into the sunset

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 51 minutes

Price per night from

$165

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.

Price per night from

$127

DOWNTOWN WITH A VIEW!Entire Home w. huge Terraces

Montepulciano house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 30 minutes

Price per night from

$247

Country House at Antico Podere in Montepulciano, Tuscany

Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$149

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

Acquaviva di Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 14 minutes

Price per night from

$198

Villa Viole - Dream under the tuscan sun

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$186

Beautiful apartment with pool in Montepulciano

Valiano apartment

3 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 45 minutes

Price per night from

$211

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

Acquaviva di Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 14 minutes

Price per night from

$87

Apartment "Poggino" - Montepulciano

Acquaviva di Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 14 minutes

Price per night from

$123

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.

Price per night from

$322

L'ANTICO GRANAIO

Montepulciano cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$154

Ostro Bed & Breakfast at Montepulciano in Tuscany

Montepulciano b&b

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$123

Room in a tower between Cortona and Montepulciano

Montepulciano b&b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$112

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.

Price per night from

$130

Holiday home casa Ciliano

Montepulciano apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$105

Apartment "Pratino" - Montepulciano

Acquaviva di Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 14 minutes

Price per night from

$111

Le Manzinaie - Glicine - Romantic apartment in Tuscany

Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$118

A view from the top

Montepulciano apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 51 minutes

Price per night from

$173

Apartment Il Ciliegio

Valiano apartment

2 bedrooms / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 45 minutes

Price per night from

$161

The Molinaccio 3

Montepulciano villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$455

Podere Monti

Sant'Albino villa

7 bedrooms / 8 bathrooms / sleeps 21

Price per night from

$552

The Molinaccio 7

Montepulciano villa

7 bedrooms / 8 bathrooms / sleeps 16

Price per night from

$989

Le Manzinaie - Limoni - Dream apartment in Tuscany

Montepulciano apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$118

Viewing 38 of 3,898
rentals in Montepulciano

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About Montepulciano

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.

Top Destination reviews

CasaMontepulciano, In the heart of Montepulciano
Great Launchpad

Casa Montepulciano is in a wonderful heart-of-the-city location. Excellent wineries, shopping, sightseeing and dining a very close by. The apartment is generously sized. One queen size bed and in the other a twin. Two bathrooms with shower, sink, toilet and bidet. Full kitchen without microwave. Wireless internet works well. There us a steep staircase to climb to enter the unit. Luca is a very charming host. He will guide you to the apartment, get you settled in, and assist with whatever your needs may be. The apartment has a minibar with wine and spirits. There is also a clothes washer for your convenience. Only drawback was the lack of additional bath towels. This is definitely a property at which we would stay again, a a city we look forward to visiting again.see more
Villa LA VALIANA (Montepulciano)
Enchanting villa, gorgeous scenery and lovely hosts!

We stayed at La Valiana in September 2012. Our stay was everything we could have asked for. The villa itself was beautiful, spacious, tastefully decorated, with modern amenities. The grounds were gorgeous and lovingly cared for. The pool was immaculate and there were many areas (balconies, tables, lounge chairs, etc.) for enjoying the outdoors. Every morning we would go out and pick lemons, figs, and various vegetables from the garden. The villa is surrounded by olive trees and rows of vines. We were lucky enough to be there during the grape harvest! All of the grapes were harvested by hand. We were also able to purchase wine made from grapes grown on the property, which was quite special. One of the region's to producers, Avignonesi, was within walking distance. The region itself is fantastic. The villa is set in the Tuscan hills; the towns of Montepulciano and Cortona are visible from the villa. It is a wonderful base from which to explore the region. Finally, the owners, Cecilia and her parents, are wonderful hosts. They are very welcoming and made us feel very special. They really wanted us to enjoy and appreciate their region, and were excellent ambassadors. I have very fond memories of our stay there and would return in a heartbeat.see more
Poggio Etrusco: Tuscan B&B, apts, & Cooking School
The Perfect Stay

Experience a "real" taste of Italy. Stay in a really cool, old farm house back off the road next to their own vineyard. Pam and Johnny are great and very knowledgable of the of the area and will help you plan your day. Take a cooking class and bring home some tasty memories from the delightful B&B.; It is off the main road a couple of kilometers, but that means No road noise! Just the sounds of the Italian hills.see more
Tigli #2, apt Montepulciano area for 5 persons with A/C, Wi-Fi and swimming pool
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 balcony had cover we rugged up and enjoyed the stunning view with a glass of wine! The two main bedrooms were spacious and comfortable the third a small single was fine. The kitchen was well equipped and living room comfortable. The only negative was the staircase that had a wooden beam by kitchen and balcony door which was at head height and very easy to take a nasty knock on the head( as I did) it really does need something done as it is dangerous. We were the only people other than a young Dutch couple there so it was very tranquil but the lay out of the apartments is such that there should not be much in the way of intrusive noise even when fully occupied. Every apartment had its own personal outdoor space and access to lots of shared space. If you arrive late on a Saturday or anytime Sunday it is difficult to buy supplies but that is true over most of Tuscany. There are lots of lovely places to eat and drink within a short drive however nothing within walking distance. All in all a fantastic holiday the caretakers couldn't have been more helpful and pleasant would definitely go back sometime.see more
Tigli #5, flat near Montepulciano with 2 bedrooms. A/C, Wi-Fi and swimming pool
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 villages to explore. You 100% need a car here but we didn't mind - we had some lovely drives to local towns and villages to explore and try their wonderful food. You are 5 minutes drive from Montepulciano and 10-15 minutes from the next nearest village/town - but you wouldn't know they were that close! (I think it is Montefollonico that has an amazing wine bar/restaurant in the middle of the courtyard) The appartment is a good size and has everything you need. Outside my the pool there is a large BBQ and pizza oven for the whole estate to use. We used the BBQ every other night and it was great. Our main concern when booking was that a young family would book the same time as us (there are a few other appartments there) and ruin the tranquility around the estate. When we arrived there were other families there but everything is so spaced out that we really didn't mind. Only thing that would have been nice were more sun loungers (not enough if all guests at pool) and the cleaning charge is very expensive - considering you have to clean the flat yourself before you leave and drive the rubbish up to the main road. Overall it was an amazing place to be - the estate is beautiful and very well looked after. The service was also great and friendly. Have recommended to all friends and family.see more
Tigli #1, two bedrooms apartment close to Montepulciano with Wi-Fi and pool
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 very spacious. We has al Fresco dining everynight overlooking the hills of Tuscany in Montepulciano. Fell in love with the crossed eye cat who greeted us upon our arrival.see more

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