
House vacation rentals in Montalcino
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Top-rated house rentals in Montalcino
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Popular amenities for Montalcino house rentals
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.

Vacation immersed in the Tuscan countryside 'Canaiolo'
We reached the destination and immediately felt like being at home. Such a nice country-house, quiet surroundings and a most gorgeous and large pool. Gary, who looks after everything, is one of the nicest hosts we have ever met: charming, helpful and making you feel very comfortable. A highly recommendable place to stay! Anne and Werner from Austria

Villa in Umbria with pool
Antonio is a very nice host who always takes care of the house and his guests. The 4 apartments were very good and also convenient for our group vacation. Parking is more than enough on the property as cars are also mandatory to get to the house. Furthermore, the pool is very good and also very large. Enough space to have fun. Antonio came several times to clean the pool, which was very good. Other shade options such as umbrellas or another pavilion would be good, otherwise you have to take them with you beforehand.

Villa in Tuscany - Reggello, with Swimming Pool and WiFi.
Very nice place to stay in the hills of Tuscany. A little remote but we appreciated that. Many restaurants nearby with really very good food and absolutely good prices. Accommodation with large garden, pool, air conditioning and heating. Well-kept and clean. Chickens whose eggs we were allowed to collect. Magena was always available, very friendly and helpful. Many wineries in the area where you can eat and drink. We will be back. Thanks Magena and Eduardo

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.

Beautiful bright villa with view - Casa Luca
We stayed at Mel's Casa Luca in March 2025 for over a week. Tucked away yet near medieval Campagnatico, it’s 5 minutes from the E78 to Grosseto/Siena, 15-20 minutes to Grosseto, and 30 minutes to the sea. Casa Luca, one of three stone farmhouses on what is essentially an olive farm, offers resort-like amenities which are shared with the guests of the other 2 houses: a trampoline, large pool, and ample walking space. Casa Luca is a single-storey house with two bedrooms with plenty of storage, comfy beds, an open-plan kitchen/dining/living area with Netflix, a big bathroom, and a well-equipped kitchen. Outside, there’s a private garden, terrace, BBQ. There is also a shared bakehouse with a pizza oven and huge dining table. We loved it and highly recommend it!

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

La Casa del Briga
A very nice stay, in a beautiful area, complete relaxation in the middle of nature, near charming villages. Very large and well cared for house, with excellent amenities. A beautiful garden, overlooking the hills. Very well-stocked dispensing of breakfast products and more. The gifts of wine, egg and Easter dove are very welcome. Exceptional amenities also for our dog. Really very kind, friendly and helpful hosts. We had a great time and would have liked to stay longer. Thanks to Monia and Paolo

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.

Nada Home
We had a lovely holiday in Tuscany. The villa is surrounded by beautiful scenery with lots of day trip options nearby. We added on a cooking class with Raimondo and Viola (Nada's daughter) and learnt so much. We will definitely be making fresh pasta from now on! The villa is well equipped, and nicely furnished.

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

POMEGRANATE CAMPOPINETA
Alessandra’s place was an absolute dream. It’s picturesque with the most gorgeous view of Tuscany hills in a rustic styled rental. She was extremely helpful and attentive during our stay! Would definitely come back here next time we visit!

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.

Private villa with pool and breathtaking views
Anna’s house is stunning and tucked away in such a beautiful quiet location. The people who take care of the house were kind and our two year old loved him. Would highly recommend anyone who wants a quiet get away from the hustle and bustle of life to stay here.

The Sundial in Montefioralle
Eugenio was a great host. His place is super authentic, located in the most charming medieval village with spectacular views. Everything in the house was to our satisfaction. Eugenio was super responsive and helpful with accomodating some extra requests that we had. We were travelling for work, filming a wedding at nearby castel. Location was great for us. The public parking is only about 100 meters from the house. We were teally happy with everything. Thank you Eugenio. P.S. There is an amazing restaurant with spectacular views right in the village. They only do lunches. But wow, It was such a great find. Everyrhing in that restaurant was made from their own produce, wine from their vineyard in the valley, olive oil from their trees, all vegetables from their garden. Different set menue every day. Really recommend it. It was delicious.

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!

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.
Quick stats about house rentals in Montalcino
Total rentals
110 properties
Nightly prices starting at
$40 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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- Marina di Grosseto beach
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- Santa Maria della Scala
- Avignonesi Winery Fattoria Le Capezzine
- Cavallino Matto
- Casa Barthel
- Cala Di Forno
- Podere La Marronaia, Sosta alle Colonne
- Tenuta Le Velette
- Cala Violina
- Cantina Stefanoni
- Cantina de' Ricci
- Madonna del Latte
- Riva del Marchese
- Castiglion del Bosco Winery
- Cantina Contucci
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Golf Club Toscana
- Pubblico Palace
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Casa Del Cioccolato Perugina
- Podere Il Cocco
- Ugolino Golf Club
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