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Browse Select Montalcino Villas

Pool
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, (55)
"Where to even begin? We loved everything about our stay. Stefania was wonderful, and responsive to our many questions before we even arrived. Upon arrival, it felt like a dream. The Villa is beautiful, private, and expansive. The property is huge, with lots of olive trees, fig trees, and places for the kids to play and explore. And not to mention the stunning pool, which overlooks the most incredible views of Cortona. We were pleased to find a ping pong table, and just absolutely loved the pool...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
A heated pool
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
10.0 out of 10, Exceptional, (37)
"Three generations of our family spent two weeks at this beautiful villa, and it was a very special vacation. The villa, grounds and pool are maintained in perfect condition - just the right combination of old-world charm with modern conveniences. The kids loved the pool, and the adults very much enjoyed the cocktail hour in the beautiful grounds by the pool at the end of the day. We love to cook, as a family, and found everything we needed to prepare meals in the huge kitchen. We also had...
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Outdoor dining
Magnificent Leopoldian Villa for 10p (+option. 4p) with private pool and garden
10.0 out of 10, Exceptional, (17)
"Villa Gagnoni is a well restored authentic Tuscan farmhouse in a superb, tranquil "away from it all" natural setting. It is an excellent, well located base for exploring central Tuscany with many of the top attractions anywhere from a short drive to an easy day trip away. The nearby village of Lucignano is charming. The quality of the architectural restoration is of a high standard. The furnishings include some impressive antique sideboards and wardrobes and is otherwise comfortably...
Magnificent Leopoldian Villa for 10p (+option. 4p) with private pool and garden
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Outdoor pool
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.
10.0 out of 10, Exceptional, (2)
"The property is extremely well maintained and feels brand new. The location is perfect for exploring wine country and villages! The property manager is extremely responsive and helpful, and went as far as stocking groceries prior to our arrival and preparing dinner for us the first night. We were very happy with our experience."
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.
Exterior
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
10.0 out of 10, Exceptional, (5)
"Our large family of 12 spent 5 days at Podere Casetta and we absolutely loved it. There was plenty of living space to accommodate our party size and everyone slept comfortably. The property was postcard beautiful capturing all that you could expect from a Tuscan getaway. Everyone had a blast with on-site activities such as a pool, jacuzzi, ping pong, and volleyball. I can not say enough about our hosts Liesbeth and Giacomo. They were fantastic and pleasure to deal with. During our last night,...
Siena, True Tuscany! EntireProperty in exclusive 20P Fenced Pool A/C HotTub WiFi
Fridge, microwave, oven, stovetop
Vintage Villa Vagnucci - Cortona
10.0 out of 10, Exceptional, (1)
"Have stayed in area before, but not Cortona. We were taken around the property by Nonna and her grandson. A great team. They bogg live on siteNonna was attentive but not intrusive, and always left us tomatoes and basil from her garden, but spoke no english - more of a comment about us than her as it would have been great to talk to her more fully. A lovely lady. Stefano was great as translator, go to guy for info - taxi firms, air con specialists, bar to watch womens footy final! Etc A great...
Vintage Villa Vagnucci - Cortona
Fridge, microwave
Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren
10.0 out of 10, Exceptional, (1)
"Bellissimo casolare ben tenuto con magnifico giardino e grande piscina. La padrona di casa gentilissima e molto discreta. Abbiamo soggiornato in agosto con amici e ci siamo trovati benissimo. Assolutamente consigliato!"
Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren
Pool
Villa with unique view of Siena with private pool
10.0 out of 10, Exceptional, (3)
"It was a special family get away to celebrate a 60th wedding anniversary. The Villa is spectacular, but the views are incredible! We even watched a hot air balloon fly over Siena at dawn! Everything we could need to cook at the Villa was provided, we hired a chef on night and he had everything he needed as well! It’s wonderfully close to Siena but also some other great little towns to bike or drive too. It was great to have our host next door when we had some questions, but it was very easy to...
Villa with unique view of Siena with private pool
Exterior
Gorgeous Comfortable House with Garden & Pool - Its all yours.
10.0 out of 10, Exceptional, (15)
"We loved our stay at “Villa Rosa”. The owner was very informative and provided all the detail and recommendations we would ever need. Alex the property manager was there to greet us to show us around and later provided further answers. The Villa is very comfortable with all the amenities you could possibly need. Great Wi-fi too. We enjoyed particularly the pool area which is very private and secluded with great views over the rolling hills. My husband is a keen wildlife enthusiast, so he was...
Gorgeous Comfortable House with Garden & Pool - Its all yours.
Property grounds
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!
10.0 out of 10, Exceptional, (2)
"Such a quaint home, clean, quiet and beautiful. Close to the center of the very small town of Montepulciano. The host is very sweet and even cooked a cake to welcome us to their home. The view of the valley from the home is simply breathtaking."
The price is CA $383
CA $472 total
includes taxes & fees
Jun 5 - Jun 6
Magnifica villa in toscana, 7 posti letto, con vista incredibile!!
Pool
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
10.0 out of 10, Exceptional, (98)
"We were group of 16 adults and three children under the age of three. Sonja and Diego could not have been better hosts! They are truly lovely people! Everything was absolutely perfect! The villa is stunning and very child friendly! We opted to have Sonja cook breakfast and dinner for us each day, and her food was absolutely delicious! You must try their pizza and bbq! We enjoyed the tennis court, feeding the horses, and day trips to Siena, Florence, and Montepulciano. The villa location is...
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
Outdoor pool
Tuscan stone villa with private pool surrounded by greenery
10.0 out of 10, Exceptional, (83)
"My family and I had been planning a trip to Tuscany for over 10 years, then one day we just decided it was time to go, so after much research, I found this gorgeous villa in Arcidosso, and booked it. I have never looked back. From the moment I booked the villa, it just felt right. Margo and Marco met us in Arcidosso where they escorted us to the villa. I fell in love with it from the moment I saw it. It was better to look at in real life than the pictures. It was absolutely perfect. The villa...
Tuscan stone villa with private pool surrounded by greenery
Interior
Il Poggio dell'Eremita
10.0 out of 10, Exceptional, (37)
"The host was very welcoming upon arrival and gave us a great tour of the property along with some area history. Such a peaceful setting. Really enjoyed the patio upstairs off the bedroom. Great views of the terrain by day and fantastic views of the stars at night. Very close to the enchanting villages on hilltops nearby (Rigamagno and Scrofiano)."
Il Poggio dell'Eremita
Pool
Stunning private villa for 4 people with WIFI, pool, A/C, TV, terrace and parking
9.8 out of 10, Exceptional, (27)
"Nice house suitable for a family of 3-4. Two bed rooms, one with a double bed. Living room and well equipped kitchen. Very cozy property a kilometer or so from the town center. The host family lives in another house on the same property, and are very nice and hospitable, while not being intruding in any way. The private church on the property is worth a visit, it was built in 710 a.d. and has frescos from the 1500s inside. The pool is very nice, and there is a nice playground for children. We...
Stunning private villa for 4 people with WIFI, pool, A/C, TV, terrace and parking
Outdoor pool
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
9.8 out of 10, Exceptional, (90)
"We had the most amazing time at Il Poggio! The property is well maintained, Roberta and Marina were incredible, and the location could not be beat. We took day trips (by car) to Siena, Arezzo, Florence, Orvieto, and Montalcino, all of which were easily and quickly accessible. Each of our five guests (two couples, one single!) had their own floor and bathroom. We cooked in the well-stocked kitchen, drank wine while watching the sunrise on the patio, and were transported to the past walking...
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Pool
Villa with private pool on 25 acres in the heart of Chianti, close to Siena
9.8 out of 10, Exceptional, (63)
"The house is well equipped and perfect if you are looking for a quiet and out of the way house. Still a quick drive to Siena where everything can be found. would definitely recommend."
Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Exterior
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
9.6 out of 10, Exceptional, (32)
"Wonderful villa with everything you need. The only downside is that there is no air conditioning when it's +40 outside, but having the windows open and a draught saved the day. Very good pool, although it's half an hour to the sea. We had a memorable holiday."
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
Pool
Villa Primula - Holiday Rental in Cortona, Tuscany
9.6 out of 10, Exceptional, (45)
"A great villa for a 3 generation group; lovely pool and garden with plenty of outside furniture. Cafes, shops and transport are within walking distance. Spacious rooms and well equipped kitchen. Owner very helpful."
Villa Primula - Holiday Rental in Cortona, Tuscany
Pool
A private luxury retreat in Montalcino
9.4 out of 10, Exceptional, (48)
"I did not want to leave. Cheerful, stylish color pallet & decor. Good internet. Postcard views. Peaceful. Relaxing. Lovely outside terrace & pool. The quibbles-no television, no coffee machine, no microwave. Sofa & coffee table are more shabby than chic. Stains. Need replacing."
A private luxury retreat in Montalcino
Pool
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
9.4 out of 10, Exceptional, (39)
"Just on the slope nestled between Cortona city and the Calcinaio church, the location was perfect for us. We enjoyed the serenity of no one immediately around us while only being a very short drive from the city walls. (Admittedly, we could have walked, but driving was easier!) Taking day trips to various Tuscan cities and sights was wonderfully served by the central location."
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
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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.

Other property types in Montalcino

Fridge, stovetop, coffee/tea maker, cookware/dishes/utensils
The Gelda house, relax with a view
10.0 out of 10, Exceptional, (6)
"This apartment is in a charming medieval village just outside Montalcino that brings you back in time. The views are phenomenal. The apartment is very comfortable and with all the amenities! The host Francesco is amazing and helped us with planning some outings while in town. Highly recommend!"
The price is CA $148
CA $204 total
includes taxes & fees
May 20 - May 21
The Gelda house, relax with a view
Exterior
The House of Alice, charm and relaxation
9.6 out of 10, Exceptional, (42)
"This place was so pretty and away from the touristy areas. We were able to see San Giamigano (sp?). Siena, Montepulciano, Montalcino was very close by. This place is in the middle of the prettiest part of Tuscany!! The place was very nice but could use some racks or hooks for your towels and a place to put your shampoo etc. by the shower. 😁"
The price is CA $192
CA $260 total
includes taxes & fees
May 19 - May 20
The House of Alice, charm and relaxation
Pool
A private luxury retreat in Montalcino
9.4 out of 10, Exceptional, (48)
"I did not want to leave. Cheerful, stylish color pallet & decor. Good internet. Postcard views. Peaceful. Relaxing. Lovely outside terrace & pool. The quibbles-no television, no coffee machine, no microwave. Sofa & coffee table are more shabby than chic. Stains. Need replacing."
A private luxury retreat in 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.