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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Villas in Montalcino and around

Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Terrace/patio

Villa in Poggiarello-ripa with 3 bedrooms sleeps 5

10.0 out of 10, Exceptional, (110)
"We loved our stay, it was beautiful and relaxing beyond words! Francesca and her team were amazing, providing so many memorable experiences and great support! We will be back! What a wonderful time all around. "
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
Villa with pool and garden
Outdoor dining

Villa with pool and garden

10.0 out of 10, Exceptional, (1)
"Top"
Villa with pool and garden
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

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

10.0 out of 10, Exceptional, (82)
"Luigi was very helpful. We had a chef 3 nights that he helped facilitate. Beautiful location. "
Villa in Montalcino, exclusive for you, stunning view!!!
Il Poggio dell'Eremita
Exterior

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (53)
"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."
The price is €156
includes taxes & fees
12 Sept - 13 Sept
Il Poggio dell'Eremita
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
Exterior

Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool

10.0 out of 10, Exceptional, (54)
"We had the trip of a lifetime at this wonderful home. Sherri, the property manager, made sure we had everything we needed upon arrival and organized a truffle hunt and wine tasting with her lovely local connections. She also introduced us to her favorite restaurants nearby (they were amazing) and told us where to shop. And the house itself is stunning- it should be in a movie about Tuscany. Cannot wait to go back!"
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Terrace/patio

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

10.0 out of 10, Exceptional, (52)
"we had a amazing time staying at this beautiful Villla. I highly recommend it to anyone!"
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Villa with private pool, air conditioning near wineries at 3km from village
Outdoor dining

Villa with private pool, air conditioning near wineries at 3km from village

9.4 out of 10, Exceptional, (42)
"Guido’s home in Tuscany is great! My family had an awesome time enjoying the pool, the near by wineries and a cooking class at the villa. The house is rustic, charming and in a great location. The beds are a bit old and the showers were a little small but overall the house fit all the needs of my family. The pool was also excellent and the views from the pool area are incredible. Whenever we needed anything it was always answered quickly. Thanks for an awesome stay!"
Villa with private pool, air conditioning near wineries at 3km from village
Stunning Villa: 24 guests, private SwimmingPool
Exterior

Stunning Villa: 24 guests, private SwimmingPool

9.8 out of 10, Exceptional, (28)
"We had a fantastic time at the house, Fabio was excellent in his communication and help. The house is great with separate areas but big communal spaces. We had a couple of delicious meals cooked for us by Fabio, I would highly recommend this luxury! If I had to say one thing it would be great if the pool seating area was tiled instead of grass, but overall can't fault it."
Stunning Villa: 24 guests, private SwimmingPool
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Exterior

BEAUTIFUL VILLA with private Pool in the heart of Chianti

10.0 out of 10, Exceptional, (25)
"We celebrated our baby turning 1 with family and friends and this property was an absolute dream! It comfortably fit our large group! We had a private chef host a dinner for us that Alessandro requested which was incredible! We are grateful for the family memories and would 100% return! Thank you for being such a great host! "
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
Outdoor dining

Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany

10.0 out of 10, Exceptional, (42)
"We spent a few nice days in spring '25 in Cortona"
Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany
Stunning private villa for 4 people with pool, A/C, WIFI, TV, terrace and parking
Exterior

Stunning private villa for 4 people with pool, A/C, WIFI, TV, terrace and parking

9.8 out of 10, Exceptional, (29)
"Mooie woning met een grote tuin en fijn zwembad. [English translation courtesy of Easy Reserve] Beautiful home with a large garden and lovely pool."
Stunning private villa for 4 people with pool, A/C, WIFI, TV, terrace and parking
Luxury Cortona view hilltop Villa
Outdoor pool, a heated pool

Luxury Cortona view hilltop Villa

10.0 out of 10, Exceptional, (48)
"The location and accommodations are perfect for a family. Nestled in the Italian countryside providing easy access to the nearby renaissance villages, art and landscapes and the people of Italy. The accommodations that Mieke has provided will only put a smile on your face."
Luxury Cortona view hilltop Villa
Villa Podere Belvedere
Pool

Villa Podere Belvedere

9.8 out of 10, Exceptional, (14)
"Thank you for making our trip so enjoyable - great hospitality!"
Villa Podere Belvedere
Villa with unique view of Siena with private pool
Property grounds

Villa with unique view of Siena with private pool

10.0 out of 10, Exceptional, (6)
"I booked Letizia's amazing Villa for a week-long birthday celebration and we loved every minute of our time in the Tuscan sun! It was great to be able to relax by the pool in the peace of the countryside amongst the olive groves while still being only a short walk away from Siena, we just wish we could have stayed for longer!"
Villa with unique view of Siena with private pool
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Property grounds

Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona

9.2 out of 10, Wonderful, (45)
"We liked our stay very much"
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena
Property grounds

Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena

10.0 out of 10, Exceptional, (3)
"This was the epitome of staying in an authentic Villa, with amazing views of the Tuscany countryside. "
Relaxation in the green, in the municipality of Monteriggioni just 7 km from Siena
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Exterior

Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!

9.8 out of 10, Exceptional, (98)
"🌟 A Perfect Stay in a Beautiful Villa 🌟 We had a wonderful time staying at this villa! It was incredibly spacious and comfortably accommodated all six of us. The house was thoughtfully equipped with everything we could possibly need, making it feel like a true home away from home. The shared pool—only between three villas—was clean, peaceful, and felt very private, which was a lovely bonus. One of our favorite parts of the stay was exploring the scenic walking trails through the surrounding...
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
XIII Century Tower with Private Panoramic Pool
Exterior

XIII Century Tower with Private Panoramic Pool

XIII Century Tower with Private Panoramic Pool
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Exterior

Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool

10.0 out of 10, Exceptional, (2)
"Beautiful villa in fantastic location . Easy to get to many places and attractions. Well equipped and very comfy beds. Lovely helpful owner. Would love to return."
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Villa Larniano, With Private Pool And View On Vineyard
Outdoor dining

Villa Larniano, With Private Pool And View On Vineyard

10.0 out of 10, Exceptional, (65)
"We had a lovely stay with 7 of us. There was plenty of area to walk and explore. We loved our wine tour with Lorenzo and our dinner with chef Robin. The house is close to the big grocery store and Siena."
Villa Larniano, With Private Pool And View On Vineyard
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

Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"Great hotel and lovely staff in a perfect location. Will book here again next time in Siena "
David 2-night trip
Posted 3 days ago
Hotel Chiusarelli

Frequently asked questions

How much do villas in Montalcino cost?
Prices for villas in Montalcino range between €156 and €156 per night. Whatever your budget, you can find a place that matches your needs with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Montalcino?
You'll find 1781 villas in Montalcino. No matter if you're taking a trip with the kids or organising a weekend break with friends, Expedia will help you find the ideal base for your squad.
Why book your villa in Montalcino with Expedia?
Reserving a villa in Montalcino is as simple as clicking on your travel dates and picking a place that has what you need. Looking for something upscale or budget friendly, or a stay that also includes WiFi and a hot tub? Use Expedia's search filters to narrow your results and find the ideal fit at the right price.