Search Vacation Homes in Montalcino

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 1341 Vacation Homes in Montalcino with updated reviews, rates, and availability.

Borgo Argiano
Terrace/patio

Borgo Argiano

10.0 out of 10, Exceptional, (65)
"Very comfortable stay. "
Borgo Argiano
The House of Alice, charm and relaxation
Interior

The House of Alice, charm and relaxation

9.8 out of 10, Exceptional, (59)
"Beautiful accommodations, very remote and tranquil, loved the area and had a great time at the local restaurants.💕 Will be back!"
The price is AED 753
AED 963 total
includes taxes & fees
11 Jun - 12 Jun
The House of Alice, charm and relaxation
Detached villa with panoramic garden
Outdoor pool

Detached villa with panoramic garden

9.8 out of 10, Exceptional, (53)
"We had a great stay at the house of Marisa and Paolo. Both were very welcoming, and we spent a perfect week in Chiusdino. The house provided everything we needed for our family of four. From the garden we had a beautiful view towards the hills. And the swimming pool was great to cool down and escape from the summer heat. Chiusdino provides a couple of good restaurants which are all in walking distance. We usually had our morning coffee in the bellavista bar, which rightfully has this name. For...
Detached villa with panoramic garden
Villa Le Tortore Tuscany private luxury pool relax
Pool

Villa Le Tortore Tuscany private luxury pool relax

10.0 out of 10, Exceptional, (88)
"Loved our 10 days staying here couldn’t fault anything! Amazing location, would love to return."
Villa Le Tortore Tuscany private luxury pool relax
Casa Fontelunga, Tuscan holiday villa with private pool
Outdoor pool

Casa Fontelunga, Tuscan holiday villa with private pool

9.4 out of 10, Exceptional, (8)
"We had a two week escape in the Tuscan countryside. We enjoyed touring around the area and a organized cooking class"
Casa Fontelunga, Tuscan holiday villa with private pool
Charming apartment in the Historic Center of Siena
TV, books

Charming apartment in the Historic Center of Siena

10.0 out of 10, Exceptional, (16)
"Excellent!"
Charming apartment in the Historic Center of Siena
Farmhouse in the hills with panoramic view and swimming pool
Pool

Farmhouse in the hills with panoramic view and swimming pool

9.6 out of 10, Exceptional, (69)
"Was wonderful and beautiful. "
Farmhouse in the hills with panoramic view and swimming pool
Farmhouse in the greenery of the Tuscany countryside with private pool and view
Outdoor pool

Farmhouse in the greenery of the Tuscany countryside with private pool and view

9.6 out of 10, Exceptional, (47)
"Wonderful garden, swimming pool and house, nice welcome by Marina."
Farmhouse in the greenery of the Tuscany countryside with private pool and view
Private House with Exclusive Swimming Pool Heated and Amazing View
Beach

Private House with Exclusive Swimming Pool Heated and Amazing View

9.6 out of 10, Exceptional, (51)
"Everything was great. The pool was warm. Views are fantastic stretching out to the sea. The town has a good supermarket. Only went to one restaurant, Dell'Upo, but it was good so went back most nights. The hosts were helpful and informative. Planning a return."
Private House with Exclusive Swimming Pool Heated and Amazing View
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Outdoor dining

Casa Bacco - private house with a remarkable garden in the centre of Cortona

10.0 out of 10, Exceptional, (5)
"This home was outstanding from the moment we arrived. There were 6 adults and we had plenty of room to gather together. The courtyard is lovely for early morning coffee or evening wine. Close to everything that Cortona offers."
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Enchanting tuscan house, private garden, wellness, stunning views, easy to reach
Pool

Enchanting tuscan house, private garden, wellness, stunning views, easy to reach

10.0 out of 10, Exceptional, (21)
"Really enjoyed my time staying at Casa Marta. Such a great location and an unbeatable view. We hope to be back again soon."
Enchanting tuscan house, private garden, wellness, stunning views, easy to reach
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Outdoor dining

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (11)
"Had a great time visiting the area. The home is beautiful. "
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
Outdoor dining

Casa delle Rose: charming house with stunning balcony in the heart of Cortona

9.6 out of 10, Exceptional, (12)
"Everything was amazing! We were a little late and they accommodated us and made everything so easy. Thank you again for the hospitality and professionalism! "
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga
Outdoor pool

Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga

9.6 out of 10, Exceptional, (4)
"The villa was so comfortable and lovely. Michele was very responsive and helpful. 10/10 experience."
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
Interior

Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni

10.0 out of 10, Exceptional, (17)
"The apartment is very large, beautifully decorated, and is in a fantastic location in Siena. Couldn't be better..... Gianluca was the perfect host. We were very happy!!! Will rent again for sure!!!"
Domus Nannini SPA - Palazzo Nannini - Loggia Salimbeni
Eco house with pool and fantastic views
Pool

Eco house with pool and fantastic views

8.6 out of 10, Excellent, (7)
"Ci siamo trovati molto bene in questa struttura, spaziosa, ed accogliente. Abbiamo usata anche la piscina perfetta"
Eco house with pool and fantastic views
Stone farmhouse near Massa Marittima, with incredible view until the Elba island
5 bedrooms, desk, iron/ironing board, travel crib

Stone farmhouse near Massa Marittima, with incredible view until the Elba island

9.8 out of 10, Exceptional, (39)
"Good location to be"
Stone farmhouse near Massa Marittima, with incredible view until the Elba island
The Old Fashion House
Smart TV, fireplace

The Old Fashion House

10.0 out of 10, Exceptional, (5)
"This was the perfect spot in Cortona right on the main street. This place met all our expectations and was as advertised."
The Old Fashion House
Air Conditioned 15th Century House with Pool on Wine Estate
Smart TV, fireplace, DVD player, books

Air Conditioned 15th Century House with Pool on Wine Estate

10.0 out of 10, Exceptional, (65)
"Beautiful peaceful place to stay. Well stocked with everything we needed and comfortable living spaces."
Air Conditioned 15th Century House with Pool on Wine Estate
Exclusive Stone Tower.
Exterior

Exclusive Stone Tower.

9.6 out of 10, Exceptional, (5)
"The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and...
The price is AED 331
AED 582 total
includes taxes & fees
8 Jun - 9 Jun
Exclusive Stone Tower.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free