Montalcino Holiday Rentals

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Montalcino

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

9.4 out of 10, Exceptional, (66)
"What a lovely place, I will recommend this fabulous home to friends and family and will be returning sometime soon."
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Villa in Montalcino, exclusive for you, stunning view!!!

10.0 out of 10, Exceptional, (84)
"Lovely villa in a beautiful location. "
Villa in Montalcino, exclusive for you, stunning view!!!

Hilltop house in the heart of Tuscany with private pool

9.8 out of 10, Exceptional, (93)
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."
Hilltop house in the heart of Tuscany with private pool

The House of Alice, charm and relaxation

9.8 out of 10, Exceptional, (66)
"Unbelievable ambience and beauty of the region and the house. Francesco was super helpful. "
The price is NZ$435
includes taxes & fees
29 Oct - 30 Oct
The House of Alice, charm and relaxation

Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

10.0 out of 10, Exceptional, (56)
"Beautiful property comfortable beds. Amazing views room two sit outside and enjoy sunsets."
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

Corte Francigena

9.8 out of 10, Exceptional, (6)
"Loved everything about my stay"
The price is NZ$340
includes taxes & fees
18 Oct - 19 Oct
Corte Francigena

Montalcino Villa - Breathtaking Views of the Val d'Orcia

9.8 out of 10, Exceptional, (46)
"We had a wonder stay at the villa. Gave a true Tuscan countryside experience in a luxurious, comfortable and convenient location."
Montalcino Villa - Breathtaking Views of the Val d'Orcia

Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.

10.0 out of 10, Exceptional, (13)
"Impeccable property. Property manager was simply amazing, welcoming, caring, friendly and always willing to help. We would love to come back! "
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.

Antico Brunello

The price is NZ$14,641
includes taxes & fees
18 Oct - 19 Oct
Antico Brunello

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (70)
"Delightful stay. The room was lovely, and the view from our private terrace was wonderful. Dinner was first rate. Easily walkable into San Quirico, short drive to Montalcino, Pienza, and Montalcino. Nice massage and spa. A very good value."
The price is NZ$356
includes taxes & fees
12 Oct - 13 Oct
Casanova - Panoramic Rooms and Suites

Hotel San Gregorio

3.0 star property
9.4 out of 10, Exceptional, (129)
"Such friendly staff, loved Pienza and the property was such a good location! "
The price is NZ$250
includes taxes & fees
4 Nov - 5 Nov
Hotel San Gregorio

ApartHotel Anghel

8.4 out of 10, Very good, (327)
"Enough space for a family. We were able to walk to restaurants, grocery and old city Siena. "
The price is NZ$191
includes taxes & fees
3 Nov - 4 Nov
ApartHotel Anghel

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (182)
"Great location and friendly staff. "
The price is NZ$282
includes taxes & fees
3 Nov - 4 Nov
Il Battistero Siena - Residenza d'Epoca

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (159)
"Great Historical location."
The price is NZ$143
includes taxes & fees
3 Nov - 4 Nov
Abbadia Sicille Relais

Country house, really private pool A.C. 20 mn beaches facing Elba Island

7.6 out of 10, Good, (9)
"Die Unterkuinft entsprach unseren Erwartungen. Es war sehr ruhig und sehr sauber. Alles war gepflegt. Die Natur ums Grundstück war sehr präsent aber auch das war Erwartungsgemäß."
Country house, really private pool A.C. 20 mn beaches facing Elba Island

Tuscasì Aparthotel

9.2 out of 10, Wonderful, (22)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
The price is NZ$159
includes taxes & fees
15 Oct - 16 Oct
Tuscasì Aparthotel

Farmhouse in the hills with panoramic view and swimming pool

9.6 out of 10, Exceptional, (74)
"We‘ve spent two wonderful weeks with our two year old daughter and our dog. The house is beautifully located in the hills with no direct neighbours. The view is fantastic and we felt immediately at home in this beautiful house. We had a wonderful time and our hosts were just lovely. (We cannot say anything about the pool - except that it is huge - because we were there out of season in March when the pool was closed.)"
Farmhouse in the hills with panoramic view and swimming pool

Bosco della Spina

9.6 out of 10, Exceptional, (163)
"We enjoyed the scenery and service! Clean and comfortable. "
Bosco della Spina

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

9.6 out of 10, Exceptional, (71)
"My husband and I loved our stay here! It was so close to town and the terrace was absolutely stunning. Would definitely stay here again! "
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

Camping Siena Colleverde

3.0 star property
8.2 out of 10, Very good, (155)
"Safe, great proximity to Siena without being too close, nice pool."
Camping Siena Colleverde
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

Top Montalcino Hotel Reviews

Find out more about Montalcino

Find out more about Montalcino

Everything you need to know about Montalcino holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montalcino holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Montalcino holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montalcino holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montalcino holiday rentals we have selected for you start as low as NZ$143 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Montalcino rentals

At Expedia, we put the best Montalcino holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Montalcino?

Yes, there are holiday rentals in Montalcino close to Bosco della Ragnaia, or you can select 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 are some of the best holiday rentals that Montalcino has to offer?

Borgo Argiano: This holiday home rental outside of Montalcino is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an espresso maker. You can relax into your holiday with a garden and a library. Another good choice for your trip to Montalcino is The House of Alice, charm and relaxation.

How many holiday rentals are there in Montalcino?

With 38 Expedia holiday rentals, you're guaranteed 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 Museum of Brunello and Civic and Diocesan Museum of Sacred Art of Montalcino. Other places in town to visit include Fortress of Montalcino and Tenuta Greppo Franco Biondi Santi.

What’s a holiday rental in Montalcino like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montalcino. Holiday rentals offer amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for family trips or small group gatherings.