Vacation Rentals & Villas in Montalcino

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217 Houses

Private villa with pool in the Montalcino area. 8 persons in 5 bedrooms!

Castelnuovo dell'Abate villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$912

ART-HANGAR BY TUSCAN-EXPERIENCE

Montalcino apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$722

Pasqui Villas La Consuma :historic villa in a village ,pool, garden, view ,WiFi

San Giovanni d'Asso villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 14

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Price per night from

$806

Casale San Giovanni

San Giovanni d'Asso farmhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$342

Casa Brunello di Montalcino

Montalcino apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$443

Pasqui Villas: La Capanna,country chic house in a village:garden,pool,view,WiFi

San Giovanni d'Asso villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

“Casa Lorenzo - A perfect slice of Tuscan heaven” I have stayed at this house multiple times in the past and our entire family adores the house and location. The owner is extremely nice and charming, her caretaker is magnificent, the grounds are beautiful and the amenities within an extremely short walk are sublime. The house is perfect for a family of 5 (of any age) or for two couples and it is absolutely charming. The airconditioning works well, the kitchen is nice and functional and the bedrooms and bathrooms are perfectly nice and comfortable. It has a small swimming pool to reduce the summer heat if you wish and a functional outdoor charcoal grille. The location cannot be beat. Don't miss the restaurant next door which is one of the best in southern Tuscany. The house is close to all that the Crete Senese offers and requires extremely short drives to visit Pienza, Montalcino, and Montepulciano. We could linger here for weeks and we would not complain at all.

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$361

Luxury villa near Montalcino with an unique view. 4 bedrooms with private pool!

Castelnuovo dell'Abate villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$912

Poggio Rubino, la casa di Idolina

Montalcino b&b

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$262

Hajar Montisi Siena

San Giovanni d'Asso house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Villa Molino

Castelnuovo dell'Abate villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$809

Great rentals within 20 miles that match your search

La Tana del Bianconiglio - App. Uva

Castiglione D'Orcia apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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Price per night from

$199

Pangea Villa 8 - Heated pool when open

Seggiano villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$995

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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Price per night from

$810

vegoia

Campagnatico villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Fattoria San Martino

Montepulciano b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$1,244

Lovely and little panoramic "Mansarda"

Monticiano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

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Price per night from

$87

Agriturismo Gello - Villa with panoramic pool in Tuscany - Chianciano Terme

Chianciano Terme villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 22

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Price per night from

$711

B&B Antica Casa i Sucinelli

Serre di Rapolano b&b

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$119

Galileo apt on ground floor very typical

Sovicille apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$156

Lovely home of Olimpia in Montepulciano, wifi, wine and bikes, music and termal

Montepulciano apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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$125

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$522

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

Montepulciano villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 16

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Price per night from

$739

Casa Oliveto

Castelmuzio house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$711

Poggio Etrusco: Tuscan B&B, apts, & Cooking School

Montepulciano villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

“Beyond adjectives” There is no way to describe our stay here! Pamela and Johnny were more than welcoming. We arrived with our 7 & 4 year olds in tow...and from The gate greeting, we felt as if we were at "memee's house". Each kid had a job...gate keeping and keeping track of the red fetch toy for Bella. We had an unwarranted snafu on credit card deposits in Rome the day before...but it was of no concern to these wonderful and true hosts... Each morning, The breakfast was true to Tuscany yet appealing to the kids... we were within an hours drive of each of our potential destinations...and each evening with a game of fetch watching Bella and the kids...the hosts helped us decide upon on the next days itinerary! We will be back with the whole family in July!

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Price per night from

$1,058

Siena San Fabiano climatized villa with outdoor heated pool

Monteroni d'Arbia villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

“Perfect combo of charm, location & comfort in glorious Tuscany!” We first dicovered San Fabiano in summer 2003 and have made it a point to return with family and friends as often as we can ever since! The location is ideal for exploring Siena, all the hill towns of southern tuscany, the Chianti and even great for easy day trips to Florence. Besides the charm of this renovated farmhouse - it also has modenr comforts like ac, screened windows, kitchenettes in all the rooms and wireless internet - plus a swimming pool! We love walking into the little town of Monteroni for our morning cappucinos and hiking the trails around this lovely farm estate. Great for kids and family gatherings as well as couples. We get through New England winters by dreaming of returning to San Fabiano. Highly recommended!

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Price per night from

$1,244

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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Price per night from

$196

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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Price per night from

$196

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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$174

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

Montepulciano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$152

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Price per night from

$185

Tuscany country apartment for 4

Buonconvento apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$249

Bed & Breakfast Antica Casa I Sucinelli

Serre di Rapolano b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$119

Poggio ai Gelsi

Pienza lodge

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$573

Welcome to Villa Pia

Radicofani apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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Price per night from

$87

Agriturismo Villa Panorama - 8 posti letto - Villa esclusiva - Siena

Rigaiolo villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$597

Collosodo farmhouse with private pool

Monticchiello townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$243

The FLAT FIELD farmhouse in Val d'Orcia

Monticchiello apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$249

luxury villa few steps from Pienza, outdoor-indoor swimming pool,air-conditoned

Pienza apartment

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 14

Responds fast! avg. 3 hours 3 minutes

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Price per night from

$1,600

Viewing 38 of 217
rentals in Montalcino

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