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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Villas in Brunello di Montalcino Wine Area

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

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

9.4 out of 10, Exceptional, (58)
"Lovely villa, great host. We really enjoyed our stay. "
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Il Poggio dell'Eremita
Exterior

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (51)
"Our family of 4 had such a beautiful time at this gorgeous villa. We only stayed for 2 nights, wish we stayed longer. Highly recommend!"
The price is SARĀ 566
SARĀ 657 total
includes taxes & fees
14 Jul - 15 Jul
Il Poggio dell'Eremita
Hilltop house in the heart of Tuscany with private pool
Outdoor dining

Hilltop house in the heart of Tuscany with private pool

9.8 out of 10, Exceptional, (85)
"We had a wonderful stay, the location was perfect for a short 15 minute walk into Montisi. The countryside setting was lovely and peaceful. We enjoyed being surrounded by beautiful nature, watching the deer every evening was delightful. We hope to return in the future. "
Hilltop house in the heart of Tuscany with private pool
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, (109)
"We thoroughly enjoyed our stay. Close to Siena and the home was very comfortable with everything we needed. Spectacular views!!!!"
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Terrace/patio

15th century barn fully renovated in a stylish style with gorgeous swimming pool

9.2 out of 10, Wonderful, (7)
"We had a wonderful time in this amazing barn now turned into a luxurious home with high end finishings. Spacious, comfortable, with all necessary amenities and enough privacy for all guests. All so nicely arranged up and until the smallest detail to make you feel at home and perfectly clean. The pool is perfect, with wonderful Tuscany hill views. Thereā€™s lots of private grounds with beautiful olive trees and flowers. Mido was very friendly and helpful."
15th century barn fully renovated in a stylish style with gorgeous swimming pool
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Outdoor pool

Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi

10.0 out of 10, Exceptional, (48)
"Exvellent Location close to all towns in Tuscany Good communication w Manager"
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Outdoor pool

BEAUTIFUL VILLA with private Pool in the heart of Chianti

10.0 out of 10, Exceptional, (22)
"We were a group of 4 families with toddlers and loved our stay at the villa! Alessandro was an excellent host and very responsive. The views and pool are stunning, and the house is clean and decently equipped. Highly recommended for a group stay in Chianti!"
BEAUTIFUL VILLA with private Pool in the heart of Chianti
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

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

10.0 out of 10, Exceptional, (81)
"Luigi was very helpful. We had a chef 3 nights that he helped facilitate. Beautiful location. "
Villa in Montalcino, exclusive for you, stunning view!!!
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
Exterior

Tuscany romance. Rural charm between Montalcino and sea. Relax pur

9.6 out of 10, Exceptional, (37)
"The stay was very nice. It's a beautiful property and very photogenic! We all loved it, wish we had more time to spend and enjoy the house."
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
Charming Villa with private pool between Pienza and Montepulciano
Pool

Charming Villa with private pool between Pienza and Montepulciano

10.0 out of 10, Exceptional, (45)
"We had a group of 11 stay and could not have loved our time more. The location was a great central spot to drive to different towns. We loved relaxing by the pools in the afternoons and our dinners al fresco. An incredible place to spend your vacation. "
Charming Villa with private pool between Pienza and Montepulciano
Private Villa with private pool, A/C, WIFI, patio, panoramic view, parking, close to Montepulciano
Dining

Private Villa with private pool, A/C, WIFI, patio, panoramic view, parking, close to Montepulciano

8.2 out of 10, Very Good, (22)
"80 von 100 punkten. Ein sehr schƶnes Haus mit einem super Pool. Der Besitzer ist sehr sympathisch und hat uns frisches GemĆ¼se gebracht, die Verwalterin ist Ƥusserst zuvorkommend. FĆ¼r den relatv hohen Preis dĆ¼rfte das Mobiliar jedoch in einem besseren Zustand sein. Es hat keine bequemen Sessel im Aussenbereich um gemĆ¼tlich zu sitzen, die sonnenliegen sind etwas gammlig und die Pfannen in der KĆ¼che praktisch unbrauchbar zum kochen."
Private Villa with private pool, A/C, WIFI, patio, panoramic view, parking, close to Montepulciano
XIII Century Tower with Private Panoramic Pool
Outdoor banquet area

XIII Century Tower with Private Panoramic Pool

XIII Century Tower with Private Panoramic Pool
VALIANA Luxury Villa in Montepulciano - Private Heated Pool - Free Wi-Fi
Outdoor pool, a heated pool

VALIANA Luxury Villa in Montepulciano - Private Heated Pool - Free Wi-Fi

10.0 out of 10, Exceptional, (25)
"Fantastic dinner in the vineyard!"
VALIANA Luxury Villa in Montepulciano - Private Heated Pool - Free Wi-Fi
Villa with unique view of Siena with private pool
Outdoor pool

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 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
I Cipressi, 5 bedrooms with pool near Cortona
Outdoor pool

I Cipressi, 5 bedrooms with pool near Cortona

10.0 out of 10, Exceptional, (1)
"The home is beautiful: Wonderfully decorated and lovingly cared for. Views are amazing; Caretakers are lovely and we all fell in love with Zorro the Dog. My only complaint is that the beds were only box springs and could have been more comfortable."
I Cipressi, 5 bedrooms with pool near Cortona
BORGO ANTICO - Nine Bedroom Villa, Sleeps 20
Terrace/patio

BORGO ANTICO - Nine Bedroom Villa, Sleeps 20

BORGO ANTICO - Nine Bedroom Villa, Sleeps 20
Private Villa in Tuscany 30%OFF
Fridge, microwave, oven, stovetop

Private Villa in Tuscany 30%OFF

10.0 out of 10, Exceptional, (12)
"As advertised. Clean villa, good location for visiting the major medieval hill towns. Lucignano lacks good restaurants. The house needs to add fans. The hostess- provided (for a fee) dinner in the villa was great! Friendly host. Wifi works well."
Private Villa in Tuscany 30%OFF
Casale Le Vigne, 8 pax, private pool
Dining

Casale Le Vigne, 8 pax, private pool

10.0 out of 10, Exceptional, (9)
"Group of 9 had a fantastic stay. The villa is superbly fitted out with lovely decor and kitchen equipment. The kids loved the pool as did the adults and the evening meal area was superb. Very good communication with the host who gave us some great suggestions. Loved our holiday and the villa was exactly what we needed. Very secluded so loved watching the stars with lots of local wine."
Casale Le Vigne, 8 pax, private pool
Private Villa with A/C, private pool, WIFI, TV, patio, panoramic view, parking, close to Montalcino
Pool

Private Villa with A/C, private pool, WIFI, TV, patio, panoramic view, parking, close to Montalcino

Private Villa with A/C, private pool, WIFI, TV, patio, panoramic view, parking, close to Montalcino
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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Frequently asked questions

How much do villas in Brunello di Montalcino Wine Area cost?
You'll pay between SARĀ 566 and SARĀ 566 per night for a villa in Brunello di Montalcino Wine Area. Whatever your budget, a terrific stay is just clicks away on 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 Brunello di Montalcino Wine Area?
Pack your suitcase and pick from 332 villas in Brunello di Montalcino Wine Area. For a family adventure, a getaway with friends or anything in between, Expedia will help you find an ideal stay in just a few clicks.
Why book your villa in Brunello di Montalcino Wine Area with Expedia?
Reserving a villa in Brunello di Montalcino Wine Area is as easy as entering your travel dates and choosing the option that suits your style. Searching for something affordable or upmarket, or a stay that also features a kitchen? Use Expedia's search filters to narrow your results and find your ideal pad.