Montalcino Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Montalcino vacation rentals

Pool
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Montalcino
The price is ￥1,094,654
￥1,186,642 total
includes taxes & fees
Dec 28 - Dec 29
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Standard Double Room (La Piazza) | Desk, soundproofing, free WiFi, bed sheets
B&B Le Scalette di Piazza

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (90)
"Great location and excellent staff. "
Canada
Jacek
B&B Le Scalette di Piazza
Deluxe Condo | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher
Corte Francigena

Corte Francigena

Corte Francigena
Montalcino
9.8 out of 10, Exceptional, (6)
"Loved everything about my stay"
United States
Svetlana
The price is ￥25,668
￥30,443 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Corte Francigena
Free WiFi
Affittacamere Mariuccia

Affittacamere Mariuccia

Affittacamere Mariuccia
Montalcino
9.0 out of 10, Wonderful, (11)
"The apartment was big enough, the owner very polite and helpful. But, there were bugs at our mattress... "
United Kingdom
Angeliki
Affittacamere Mariuccia
Front of property
Idolina Guest House

Idolina Guest House

Idolina Guest House
Montalcino
9.4 out of 10, Exceptional, (105)
"The room met our expectations. Fulvia welcomed us and provided all info we needed. She was lovely and the room spacious and cosy. The location was perfect for our needs and we were very pleased."
United Kingdom
Kathrin
Idolina Guest House
Interior
The Gelda house, relax with a view

The Gelda house, relax with a view

The Gelda house, relax with a view
Castelnuovo dell'Abate
9.6 out of 10, Exceptional, (14)
"Loved our stay...lovely and quiet..great location "
Australia
Lisa K.
The price is ￥18,398
￥26,125 total
includes taxes & fees
Dec 28 - Dec 29
The Gelda house, relax with a view
Exterior detail
The House of Alice, charm and relaxation

The House of Alice, charm and relaxation

The House of Alice, charm and relaxation
Montalcino (SI)
9.8 out of 10, Exceptional, (67)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
The price is ￥27,596
￥37,347 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The House of Alice, charm and relaxation
Interior
Il Borghetto - La Ghibellina Townhouse, private apartment with balcony

Il Borghetto - La Ghibellina Townhouse, private apartment with balcony

Il Borghetto - La Ghibellina Townhouse, private apartment with balcony
Castelnuovo dell'abate
9.0 out of 10, Wonderful, (2)
"Great location and a well maintained property"
United Kingdom
Matt D.
The price is ￥22,077
￥29,804 total
includes taxes & fees
Dec 28 - Dec 29
Il Borghetto - La Ghibellina Townhouse, private apartment with balcony
Outdoor pool
Antico Brunello

Antico Brunello

Antico Brunello
Montalcino
The price is ￥1,214,238
￥1,337,502 total
includes taxes & fees
Dec 28 - Dec 29
Antico Brunello
Outdoor dining
Montalcino Tuscany Home - Apartment "C" Terrace

Montalcino Tuscany Home - Apartment "C" Terrace

Montalcino Tuscany Home - Apartment "C" Terrace
Montalcino
The price is ￥25,389
￥33,484 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Montalcino Tuscany Home - Apartment "C" Terrace
1 bedroom, free WiFi, bed sheets
Room 'Camera Beige' - Beb del Musico with Private Terrace, Balcony and Wi-Fi

Room 'Camera Beige' - Beb del Musico with Private Terrace, Balcony and Wi-Fi

Room 'Camera Beige' - Beb del Musico with Private Terrace, Balcony and Wi-Fi
Montalcino
10.0 out of 10, Exceptional, (1)
"Host is very nice. The view is stunning. "
United States
Yufen Bebie W.
The price is ￥24,680
￥25,416 total
includes taxes & fees
Dec 28 - Dec 29
Room 'Camera Beige' - Beb del Musico with Private Terrace, Balcony and Wi-Fi
Exterior detail
The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views
Montalcino
9.6 out of 10, Exceptional, (17)
"Very beautiful location, clean exactly represented as advertised. A little limited for local eating. We cooked dinner in. Would recommend it to others. Cheers"
United States
David & Teri B.
The price is ￥27,596
￥37,347 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Casetta di Brunello, quiet and breathtaking views
Fridge, oven, stovetop, dishwasher
Apartment 'Casa Francesca' with Hills View & Courtyard

Apartment 'Casa Francesca' with Hills View & Courtyard

Apartment 'Casa Francesca' with Hills View & Courtyard
Montalcino
10.0 out of 10, Exceptional, (2)
"Clean property and amazing view. Great location "
United States
Angela B.
The price is ￥30,290
￥31,026 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Apartment 'Casa Francesca' with Hills View & Courtyard
Outdoor dining
Charming apartment in the historic center with large terrace and beautiful view

Charming apartment in the historic center with large terrace and beautiful view

Charming apartment in the historic center with large terrace and beautiful view
Montalcino
8.0 out of 10, Very Good, (1)
"Appartamento vecchio stile ma molto spazioso e con tutto quello che serve, posizione ottima "
Italy
Marco R.
The price is ￥18,214
￥31,828 total
includes taxes & fees
Dec 28 - Dec 29
Charming apartment in the historic center with large terrace and beautiful view
Outdoor dining
Il Borghetto - The House of Elba, rooftop panoramic terrace

Il Borghetto - The House of Elba, rooftop panoramic terrace

Il Borghetto - The House of Elba, rooftop panoramic terrace
Castelnuovo dell'Abate
The price is ￥22,077
￥29,804 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Il Borghetto - The House of Elba, rooftop panoramic terrace
Property grounds
Room 'Camera Rossa' with Shared Terrace and Wi-Fi

Room 'Camera Rossa' with Shared Terrace and Wi-Fi

Room 'Camera Rossa' with Shared Terrace and Wi-Fi
Montalcino
10.0 out of 10, Exceptional, (1)
"Host was very very kind and generous, very glad to have booked with her. No AC, but fan and open windows made it very comfortable"
United States
Sam
The price is ￥21,315
￥22,051 total
includes taxes & fees
Dec 29 - Dec 30
Room 'Camera Rossa' with Shared Terrace and Wi-Fi
Dining
Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center

Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center

Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
Montalcino
10.0 out of 10, Exceptional, (2)
"Absolutely the most stunning VRBO we have ever stayed at. Majestic In both stature and comfort. Every need anticipated and met. Communication with host and Valentina perfect. The standard of luxury located in a fairy tale setting! A must visit - we did not want to leave!! Cannot say enough about this special villa."
United States
Robert K.
The price is ￥91,804
￥162,083 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
Outdoor dining
Podere Belsogno

Podere Belsogno

Podere Belsogno
Montalcino
10.0 out of 10, Exceptional, (1)
"Charming and attentive hosts, stunning terrace with amazing views and a modern, attractive and well equipped rental that was a short walk to downtown Montalcino. We had a fabulous time and would go back again."
Canada
David P.
The price is ￥64,391
￥73,406 total
includes taxes & fees
Dec 28 - Dec 29
Podere Belsogno
Outdoor dining
Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda

Podere Belsogno-camera Lavanda
Montalcino
10.0 out of 10, Exceptional, (4)
"The stay was very pleasant, the room was very tidy and cosy. The view when waking up is breathtaking, as well as the whole place. Exactly as stated in the pictures. We were very welcomed by the host and you get a good breakfast. Would definitely come back again if I‘m in the area! Thank you very much for the stay!"
Austria
Johannes S.
The price is ￥22,077
￥25,757 total
includes taxes & fees
Dec 28 - Dec 29
Podere Belsogno-camera Lavanda
Fridge, oven, stovetop, coffee/tea maker
Charming Siena Countryside Stay

Charming Siena Countryside Stay

Charming Siena Countryside Stay
Monterongriffoli
The price is ￥33,116
￥47,650 total
includes taxes & fees
Dec 29 - Dec 30
Charming Siena Countryside Stay
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montalcino Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"The room was spotlessly clean, the staff were welcoming and helpful, and the breakfast was delicious!"
Kenneth 3-night trip
Posted 5 days ago
Hotel Chiusarelli

Find out more about Montalcino

Search for holiday rentals in Montalcino on Expedia! You can easily find your home rentals, villas, holiday apartments in Montalcino using one of the methods below:

  • View our selection of featured holiday rentals in Montalcino
  • Use the map to find apartments and other holiday homes in the Montalcino neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Montalcino while they last

Look no further and take a look at our great range of rental properties in Montalcino!

Frequently asked questions

Are there vacation rentals in Montalcino?

Yes, you can find vacation rentals in Montalcino close to Bosco della Ragnaia, or you can choose a more secluded option if you're looking for a relaxing stay. Discover why Montalcino is known for its spas and countryside. While you're here, grab a bite or have a drink at the wineries.

What's the top vacation rental that Montalcino has to offer?

Borgo Argiano: You might want to consider this vacation home rental near Montalcino, which is located on a river and has a balcony, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an electric kettle. You can relax into your vacation with a garden and a library. Some other top choices in Montalcino are The House of Alice, charm and relaxation and Enchanting tuscan house, private garden, wellness, stunning views, easy to reach.

How many vacation rentals are there in Montalcino?

With 28 Expedia vacation rentals, you're sure to find just the right place for your Montalcino stay.

What’s there to see and do in Montalcino?

Enjoy the outdoors at Val di Chiana and Val di Merse, or simply take in cultural attractions like Civic and Diocesan Museum of Sacred Art of Montalcino and Museum of Brunello. Other places in town to visit include Fortress of Montalcino and Tenuta Greppo Franco Biondi Santi.

What’s a vacation rental in Montalcino like?

Vacation rentals are privately owned properties you can book for several days or longer in Montalcino. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family trips or small group gatherings.