
House vacation rentals in Montalcino
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Top-rated house rentals in Montalcino
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House rentals with a pool

Casa Fattore - Tuscan countryside house
The stay at the Capocontro estate was very satisfactory. The entire old village is a jewel set in the greenery, with spectacular views of the woods of the Val di Chiana. The place is tidy and clean, picturesque and elegantly retro. Piero and Lella are very available in communications and suggestions of places to visit and eat. We loved the peace and quiet of the place, as well as the pool with a view. We stopped little and the weather was a little capricious, otherwise we would have enjoyed the exteriors of the farm more. Only small mole: the dishes and the fridge were not really immaculate, but nothing that can't be resolved with a sponge shot. Highly recommended for both a short and long stay, so you can enjoy the quiet of the place and visit the surroundings.

Deal 2019 Tuscany Villa le Capanne with pool
Gina’s place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.

Villa Pergo is an ancient charming country villa
Based on the previous wonderful reviews of Antiqua degli D’ulivi, a year ago we booked a three week stay in the outskirts of Cortona in Pergo. We had our kids, grandkids and dear friends with us and as we drove through the gates into the Villa, we entered a magical place filled with generosity, laughter, relaxation, wonderful food, a refreshing pool and golden light. Massi was always there to help us with any questions we had and refill our olive oil bottle with the amazing green liquid made from his olives. We enjoyed the most delicious lunch with his family and they also were such giving, lovely people. We learned so much about Italy and Tuscany from them: porcini mushrooms, Perugia soccer teams, local markets, hot springs near Montepulciano, nearby restaurants, vineyards, hikes and more. We highly recommend an extended stay at this Tuscan home—we were so fortunate to experience it for three glorious weeks. The memories will be long lasting and always treasured. Mille Grazie to Massi

Casa Arcobaleno – Città della Pieve
Such a lovely villa. Beautifully arranged with perfect amount of space for our group of 8. The villa has everything you need. The pool was lovely and warm even without being heated. Margherita, the local host, was amazing - so helpful. Would definitely come back.

L'Olivo - detached villa with swimming pool
Amazing place in a quiet area with a beautiful view of the countryside. Climate cottage equipped with everything you need. Together with our dogs we felt like at home. Bruna is an incredibly warm and helpful person. Thank you for a wonderful time.

Tuscan farmhouse near Siena + Cortona, heated pool
We absolutely loved the home and location! There were nine of us and everyone had their own space and bathroom. The home was very clean and decorated beautifully. Amanda was a fabulous host. She was very responsive with all communication and helpful with places to see in the region. The location was excellent for traveling all around Tuscany and it was very peaceful. We can't wait to go back!

Big Breathtaking PoolVilla bw Rm/Fl
Beautiful large house with great views and an amazing pool area. A little remote, at the end of a long and steep gravel road, but completely worthwhile. Great hosts, very attentive to their guests' every need.

"Casa Elisa", house with swimming pool at the foot of Cortona
I had an unforgettable stay at Casa Elisa, located at the foot of the beautiful Cortona. The atmosphere is magical: a perfect fusion of Tuscan tradition and modern comfort. The rooms are elegant and quite spacious, tastefully furnished and equipped with all the necessary comforts. The garden with pool is an oasis of tranquility, ideal to relax with a good book or to enjoy an aperitif at sunset. But it's the warmth and hospitality of Elisa's family that makes the stay really special. Their availability in providing information about places to visit and recommended restaurants makes all the difference. I highly recommend Casa Elisa to anyone who wants to discover the beauty of Tuscany, living an authentic and unforgettable experience.
House rentals with free parking

Malamerenda's House in Siena
Our stay at Giulio's was excellent. The space is cozy, everything was very clean and well maintained. Giulio was very helpful with everything we needed and always responded promptly.

Rosaspina - Poggio Alla Serra
l recommend it to those looking for a quiet, clean Tuscan country house and those who like privacy. The house was generally comfortable and spacious, but the small, cozy kitchen was not very suitable for cooking. This was not a request we needed anyway because the region offers plenty of opportunities for both the eye and the stomach. We toured Tuscany a lot and slept peacefully in the evening and woke up to the sound of birds in the morning. We were welcomed very nicely by the hosts and were informed. So thanks again to them.

House in the Center - "Casa Laura"
Cozy home just a stone's throw from the walls of Città di Castello, very convenient indoor parking. The house is very clean and functional, Laura welcomed us in person despite the torrential rain. The pie she made for us for breakfast was also excellent. Great experience.

Casa Arcobaleno - Free Parking - WiFi
Thank you Laura,we are very grateful.Your house is fantastic and you have much care in all details.We hope see you soon

casa palme
Very nice place, clean, well organized and with all the comforts of a vacation home. Alessandra was always very helpful and willing to help. Highly recommended.

The balcony
I would recommend Orvieto to anyone and this little house was an absolute gem, ideally placed and really ideal for a getaway. We definitely wish we had stayed longer☺️

Terrace a Campana
Carolina provided my family and I an incredible escape in the hills of Tuscany during our stay. Everything was well-provided, as listed, and the location also provided us the opportunity to get around more easily within the area. Thank you for making my Mother’s retirement trip so memorable, would love to come back here again in the near future!

A moment of relaxation
As soon as we entered, the feeling was that of being at home. Spacious, clean and equipped with everything you need. In addition, Francesca was very nice to leave us a fantastic and abundant breakfast. Also recommended for the location.
Weekly house rentals

Noi 2 Vacanze - Dario's House
The views are beautiful. Peaceful neighborhood. However, the kitchen is missing several items for cooking.

Beautiful property between Siena and Arezzo
we had a very nice stay. The entire accommodation was very clean. Highly recommend taking something against the mosquitoes. the only criticism was the chairs on the terrace, as 2 have shackled heavily, there should be a replacement here.

[15 min da Montepulciano] Villa Chiara
Great location and the 2 full size bathrooms were nice!

The Montebenichi Dovecote
We had an incredible stay at this beautiful villa in the rolling hills of Tuscany. Perched on a mountain, the property offers stunning views over the countryside, with gorgeous gardens and an authentic Tuscan feel throughout. The villa itself was spacious, comfortable, and full of charm. The location was perfect — peaceful and private, yet central to many of the places we wanted to visit, including Florence, Montepulciano, Siena, and San Gimignano. Christina, our contact person, was a great communicator. She was also on time, very helpful and pleasant to be around. She provided us with great insights about the area and the property. The location was excellent for us to use the e-bikes that we rented. We had breathtaking rides around the area. There was an excellent grocery store, Conrad’s in Bucine with a very tasty restaurant in the same Plaza. It was the perfect rustic home base with lots of charm the Tuscan experience for exploring the region, and we would absolutely stay again

2 / 8px house on Tuscan Borders
Andrea's place was perfect for our short two night stay in the Niccone Valley, or fav area in Umbria. We were there in cooler weather and the floor heating took a bit to come on but once it did we were comfortable. I think it would be a great place in the warmer weather as the pool looked wonderful. The Niccone Valley is somewhat remote but with the location of this property you had the best of both worlds quick access to Umbertide and yet embedded in the valley. Would love to return in the warmer weather. Thank you Andrea!

Villa Profumo di Salvia. Lakefront
We had a wonderful stay. Silvia was very responsive, and she even brought us pizza upon our late arrival! The grounds are gorgeous and the views were incredible. The villa itself was spacious, clean, and exactly as described in the listing. Highly recommended.

Authentic tuscan barn 3 bedrooms 3 bathrooms
The complex is in a larger clearing in the middle of the forest. Completely remote and quiet day or night. Pure relaxation. Well-maintained complex. Good kitchen equipment. Tastefully furnished apartment. Great pool. 14x7m. Perfect for a few laps or to romp. Location is perfect for excursions. Florence, Pisa, Siena each about 60 minutes away by car. In and around San Gimignano there are many restaurants with good Tuscan dishes. A reservation is often required if you like to move away from the tourist centers. Shopping facilities can be reached in 15 minutes. External garbage disposal at nearby collection points is a bit annoying. Laura took care of the personal key handover with us and speaks perfect German! All in all 5 stars! We will be happy to come back.

Bliss out in Historic Farmhouse on Organic Wine Estate with Tennis and Pool
We had a fantastic stay with a group of four adults and five kids. Accommodations were immaculate, private chefs were decadent and delicious, and fantastic wine. The grounds were just lovely as well and we enjoyed having a fire in the fire place every evening. That you for a lovely stay!
Quick stats about house rentals in Montalcino
Total rentals
110 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with a pool
40 properties have a pool
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- Lake Trasimeno
- Lake Bolsena
- Feniglia
- Mount Amiata
- Val di Chiana
- Gulf of Baratti
- Valdarno
- CavallinoMatto
- Marina di Grosseto beach
- Kite Beach Fiumara
- Cavallino Matto
- Santa Maria della Scala
- Avignonesi Winery Fattoria Le Capezzine
- Casa Barthel
- Cala Di Forno
- Podere La Marronaia, Sosta alle Colonne
- Tenuta Le Velette
- Cala Violina
- Riva del Marchese
- Pubblico Palace
- Cantina Contucci
- Cantina de' Ricci
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Cantina Stefanoni
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