Montalcino Vacation Rentals

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Dec 12 - Dec 14

Vacation Rentals in Montalcino

Deluxe Condo | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher
Corte Francigena

Apartment in Montalcino

9.8 out of 10, Exceptional, (6)
"Loved everything about my stay"
United States
Svetlana
$160 nightly
The price is $187
Dec 26 - Dec 27
Total with taxes and fees
Corte Francigena
Standard Double Room (La Piazza) | Desk, soundproofing, free WiFi, bed sheets
B&B Le Scalette di Piazza

Townhouse in Montalcino

9.4 out of 10, Exceptional, (90)
"Great location and excellent staff. "
Canada
Jacek
B&B Le Scalette di Piazza
Pool
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

Villa in Montalcino

$7,500 nightly
The price is $7,500
Dec 6 - Dec 7
Total with taxes and fees
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Interior
The Gelda house, relax with a view

Vacation Home in Castelnuovo dell'Abate

9.6 out of 10, Exceptional, (14)
"Loved our stay...lovely and quiet..great location "
Australia
Lisa K.
$160 nightly
The price is $165
Dec 15 - Dec 16
Total with taxes and fees
The Gelda house, relax with a view
Front of property
Idolina Guest House

Townhouse in 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
Il Borghetto - La Ghibellina Townhouse, private apartment with balcony

Apartment in Castelnuovo dell'abate

9.0 out of 10, Wonderful, (2)
"Great location and a well maintained property"
United Kingdom
Matt D.
$186 nightly
The price is $191
Dec 15 - Dec 16
Total with taxes and fees
Il Borghetto - La Ghibellina Townhouse, private apartment with balcony
Exterior detail
The House of Alice, charm and relaxation

Vacation Home in Montalcino (SI)

9.8 out of 10, Exceptional, (66)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
$243 nightly
The price is $247
Dec 5 - Dec 6
Total with taxes and fees
The House of Alice, charm and relaxation
Outdoor dining
Charming apartment in the historic center with large terrace and beautiful view

Apartment in 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.
$195 nightly
The price is $200
Dec 6 - Dec 7
Total with taxes and fees
Charming apartment in the historic center with large terrace and beautiful view
Exterior detail
The Casetta di Brunello, quiet and breathtaking views

Vacation Home in Montalcino

9.6 out of 10, Exceptional, (16)
"The apartment is beautiful and the views are breathtaking! The local restaurant serves very authentic family style Tuscan cuisine and everyone was incredibly friendly and helpful. I wish we could have stayed longer!"
Australia
Andrew M.
$242 nightly
The price is $247
Dec 6 - Dec 7
Total with taxes and fees
The Casetta di Brunello, quiet and breathtaking views
Outdoor pool
Antico Brunello

Villa in Montalcino

$7,674 nightly
The price is $8,453
Dec 12 - Dec 13
Total with taxes and fees
Antico Brunello
Fridge, oven, stovetop, dishwasher
Apartment 'Casa Francesca' with Hills View & Courtyard

Apartment in Montalcino

10.0 out of 10, Exceptional, (2)
"Clean property and amazing view. Great location "
United States
Angela B.
$171 nightly
The price is $175
Dec 24 - Dec 25
Total with taxes and fees
Apartment 'Casa Francesca' with Hills View & Courtyard
Outdoor dining
Il Borghetto - The House of Elba, rooftop panoramic terrace

Vacation Home in Castelnuovo dell'Abate

$184 nightly
The price is $188
Jan 4 - Jan 5, 2026
Total with taxes and fees
Il Borghetto - The House of Elba, rooftop panoramic terrace
Outdoor dining
Podere Belsogno-camera Lavanda

Vacation Home in 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.
$160 nightly
The price is $163
Dec 13 - Dec 14
Total with taxes and fees
Podere Belsogno-camera Lavanda
Dining
Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center

Vacation Home in 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.
$1,017 nightly
The price is $1,027
Jan 3 - Jan 4, 2026
Total with taxes and fees
Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center
Property grounds
Room 'Camera Rossa' with Shared Terrace and Wi-Fi

Apartment in 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
$135 nightly
The price is $140
Dec 5 - Dec 6
Total with taxes and fees
Room 'Camera Rossa' with Shared Terrace and Wi-Fi
Fridge, oven, stovetop, coffee/tea maker
Charming Siena Countryside Stay

Vacation Home in Monterongriffoli

$230 nightly
The price is $242
Dec 5 - Dec 6
Total with taxes and fees
Charming Siena Countryside Stay
Outdoor dining
Podere Belsogno-apartment rose garden

Apartment in Montalcino

$161 nightly
The price is $161
Dec 5 - Dec 6
Total with taxes and fees
Podere Belsogno-apartment rose garden
Outdoor dining
Podere Belsogno

Vacation Home in 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.
$464 nightly
The price is $467
Dec 5 - Dec 6
Total with taxes and fees
Podere Belsogno
Pool
Agritourism in val d'orcia

Vacation Home in montalcino

$397 nightly
The price is $397
Dec 6 - Dec 7
Total with taxes and fees
Agritourism in val d'orcia
Dining
Podere Belsogno-camera Rosmarino

Vacation Home in Montalcino

9.0 out of 10, Wonderful, (4)
"Owners live on property and were very helpful for our first visit to beautiful Montalcino in Tuscany. Spotless apartment. Walking to city center which is just lovely. Beautiful setting. We would return."
United States
Larry V.
$160 nightly
The price is $163
Dec 13 - Dec 14
Total with taxes and fees
Podere Belsogno-camera Rosmarino
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.
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Top Montalcino Hotel Reviews

Mastrojanni Relais

Mastrojanni Relais

10/10 Excellent
"This was heaven on earth!! Completely over-exceeded my expectations! Room was so nice, comfortable, and relaxing. A perfect retreat to our busy trip. Also, the wine tour and restaurant can't be missed!! "
Chris 1-night trip
Posted 3 days ago
Mastrojanni Relais

Find out more about Montalcino

Everything you need to know about Montalcino vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montalcino vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montalcino vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montalcino vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montalcino. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Montalcino in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $68 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montalcino rentals

At Expedia, we put the best Montalcino vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Montalcino rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montalcino vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montalcino. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 a coffee maker. 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 35 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 Merse and Val di Chiana, 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.