Vacation Rentals & Villas in Montalcino

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851 Houses

Cesira Palazzina

Val d'Orcia b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$193

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

Castelnuovo dell'Abate villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$912

Casal d'Asso

San Giovanni d'Asso house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 7

Price per night from

$806

La Capannina La Capannina

San Giovanni d'Asso house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

Price per night from

$325

Villa Elisa

Poggio alle Mura villa

  • 11 bedrooms
  • 13 bathrooms
  • sleeps 30

Price per night from

$1,994

Olivella Olivella

San Giovanni d'Asso house

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 10

Price per night from

$744

Alborata 10, Emma Villas

San Giovanni d'Asso villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$790

Villa San Giovanni Villa San Giovanni

San Giovanni d'Asso villa

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 14

Price per night from

$847

Podere il Sogno

Tavernelle villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$918

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

San Giovanni d'Asso villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 14

Price per night from

$822

La Casa di Alice - Montalcino

Castelnuovo dell'Abate house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$162

Podere Scannelli Suite 02

Montalcino b&b

  • 1 bedroom
  • sleeps 3

Price per night from

$199

Casale San Giovanni

San Giovanni d'Asso farmhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$343

Superb villa with pool 30 minutes from Siena and Montalcino

Montalcino villa

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$635

#la Ghibellina Montalcino

Montalcino house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$125

Scannelli Single Farm

Montalcino b&b

  • 1 bedroom
  • sleeps 1

Price per night from

$94

Scannelli Farm

Val d'Orcia b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$150

Farm House Bampton-Brunello

Val d'Orcia apartment

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$287

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.

Price per night from

$361

Agriturismo La Buca

Val d'Orcia b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$112

Agriturismo La Buca

Val d'Orcia apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$125

Podere Scannelli Bedroom 02

Montalcino b&b

  • 1 bedroom
  • sleeps 2

Price per night from

$150

Podere Scannelli Bedroom 01

Montalcino b&b

  • 1 bedroom
  • sleeps 2

Price per night from

$150

Farm House Bampton-Red

Val d'Orcia apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$249

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

Castelnuovo dell'Abate villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$912

Podere Scannelli Suite 01

Montalcino b&b

  • 1 bedroom
  • sleeps 3

Price per night from

$199

Ca 'Montalcino

San Giovanni d'Asso apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$81

Poggio Rubino, la casa di Idolina

Montalcino b&b

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$262

Spacious house for 6 ppl. at Montalcino

Montalcino house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$425

Casale Le Borghe (10 guests) - Montalcino, Tuscany

San Giovanni d'Asso villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$685

Villa Molino

Montalcino villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$489

Podere Scannelli double room 03

Montalcino b&b

  • 1 bedroom
  • sleeps 2

Price per night from

$150

#la Ghibellina2 Montalcino

Montalcino house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$75

Borgo La Bagnaia #Villa Sarageto

San Giovanni d'Asso villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

Responds fast! avg. 3 hours 43 minutes

Price per night from

$871

Villa Asciano 30 - Stunning villa with garden and pool in Val d'Orcia

San Giovanni d'Asso villa

  • 14 bedrooms
  • 15 bathrooms
  • sleeps 30

Responds fast! avg. 2 hours 19 minutes

Price per night from

$3,153

Da nonna Bruna

Montalcino apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

Price per night from

$125

Splendida Villa con Piscina privata e SPA

Montalcino villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

Price per night from

$1,182

casa per l'Osticcio con vista sulla val d'Orcia

Montalcino apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 29 minutes

Price per night from

$100

Viewing 38 of 851
rentals in Montalcino

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Top Destination reviews

Pasqui Villas La Consuma :historic villa in a village ,pool, garden, view ,WiFi
A little corner of Paradise!

We stayed in this villa for two weeks last July (2012)and we enjoyed our stay very much. The villa itself is very comfortable, nice furniture, air conditioning in most of the rooms, fans, wifi, swimming pool, in short all that can be useful for a family on vacation. The swimming pool is lovely and I particularly liked the steps to get into it. When we arrived we were greeted by the owner Federica, her passion could be felt in all the attention for details she puts everywhere in the house, also she was very comprehensive in her explanations. We opted for the "first dinner" which was a fantastic way to start off our holiday, Grazia the cook who prepared it, is a real gem and we often asked her afterwards. The villa is convenientely located close to some of the most famous Italian historical towns. Siena, Pienza, Montalcino are all a short drive away. The village of San Giovanni is itself delightful and there are shops well stocked with the famous cheeses, wine, olive oil and many other typical products. If you do not fancy cooking yourself you can ask Grazia or there are a couple of restaurants. Everybody was kind and nothing was too much trouble for them, I would like to thank Federica for the great time we spent at her house and for the lovely memories we will always treasure.see more
Pasqui Villas: La Capanna,country chic house in a village:garden,pool,view,WiFi
Lovely Holiday home

Our family of 5, including 3 teenagers, stayed in this beautiful, old house during august. It is very spacious with plenty of seating in the communal areas and beautiful decor. The large dining area was great for meals and games evenings and we made use of the BBQ supplied by the pool. The kitchen is very well appointed with everything that you could need including a basic store cupboard. Federica made us very welcome and gifts included a delicious bottle of her home produced olive oil. The boys also tell me that the wifi worked well as did the air conditioning in the bedrooms. The villa is situated in a quiet hilltop town with a great butcher's shop, a small supermarket and nice (but hard to find) bakers. Choice of restaurants in the village is small but we ate out at lunchtime on our excursions or cooked at home which suited us very well. The location is quiet and peaceful with beautiful views. There is plenty to see in the area. A highlight for us was Pienza with a fantastic ice-cream shop - Gelateria Toscana. The best we tried in Tuscany (and we did try a fair few between us!)see more

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