Vacation Rentals & Villas in Montepulciano

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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

“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

$234

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

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$190

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

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$210

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

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$173

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

$234

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

$212

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

Price per night from

$311

Apartment "Poggino" - Montepulciano

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$187

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

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$130

Borgo dei Sette Tigli #4

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Relaxing Vacation” excellent clean with all the amenities and a great view. excellent hostess Venessa who treated us to Tipica Cena Toscana dinner. Great job Venessa

Price per night from

$217

Apartment "Pratino" - Montepulciano

Acquaviva di Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$173

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

Sant'Albino villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 21

Price per night from

$808

Ostro Bed & Breakfast at Montepulciano in Tuscany

Montepulciano b&b

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$125

The Molinaccio 3

Montepulciano villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$621

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

Montepulciano studio

  • Studio
  • 1 bathroom
  • sleeps 2

Price per night from

$130

The Molinaccio 7

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 16

Price per night from

$1,242

Villa Incanto

Bivio di San Biagio villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 15

Price per night from

$743

Tenuta Senese Tenuta Senese

Montepulciano house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Price per night from

$650

Independent villa with private pool, hot tub, WI-FI, A / C near Montepulciano!

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

Price per night from

$760

Villa degli Olivi

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Price per night from

$831

16 persons with 8 bedrooms, private pool and WiFi. Only 2 km to Montepulciano!

Montepulciano villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 16

Price per night from

$738

Villa Ardita

Bivio di San Biagio house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 35 minutes

Price per night from

$979

Villa Ardene

Montepulciano villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

Price per night from

$870

Farmhouse Il Fienile

Montepulciano apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$187

Historic building in the center of Montepulciano

Montepulciano house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$460

I Tigli, apt in farmhouse only 5 km to Montepulciano. 2 bedrooms, pool and Wi-Fi

Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$234

THE POGGIARONE

Montepulciano villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$261

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

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 37 minutes

Price per night from

$143

Tuscany Villa PODERE MONTI

Montepulciano villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

Price per night from

$1,403

La Casina Toscana, central with parking and wi-fi

Montepulciano cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$143

Double room PANORAMIC VIEW

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$125

Tenuta di Argiano in Montepulciano, apartment, winery, pool, wifi

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$106

Tenuta di Argiano in Montepulciano, apartment, pool, wifi, winery, trekking

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$106

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

Montepulciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 3 hours 37 minutes

Price per night from

$205

Double rooms with bathroom and Panoramic Terrace

Montepulciano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$149

Buen retiro

Abbadia di Montepulciano lodge

  • 8 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$249

BEAUTIFUL EMERALD'S HOME IN TUSCANY

Acquaviva di Montepulciano apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$373

Viewing 38 of 1,489
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

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
Borgo dei Sette Tigli #4
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. … 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
Tigli #6, ground floor flat with one bedroom in Montepulciano area. Wi-Fi & pool
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. … see more

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