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House holiday rentals in Montalcino

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Popular amenities for Montalcino house rentals

House rentals with a pool

Guest favourite
Home in Montaione
4.94 out of 5 average rating, 104 reviews

Cercis - La Palmierina

JenniferRating, 5 stars2 days ago
We had an absolutely amazing time at Daniela’s place - it was clean, had stunning views and was quick access to Pisa, Florence & Siena. Beautiful pool and lovely terrace with amazing views and sunsets. The kitchen also had everything we needed, including local olive oil and pasta & local wine as a welcoming gift. Daniela went above and beyond providing us with lilos and a pump for the pool too. Overall, 10/10 stay!
Superhost
Home in Asciano
4.88 out of 5 average rating, 144 reviews

A Charming House in Asciano - Siena

CristinaRating, 5 stars8 months ago
Very nice place with a great view, very quiet and relaxing. The apartment was clean and cozy. The only inconvenience were the squeaky doors.
Guest favourite
Home in Orvieto
4.99 out of 5 average rating, 211 reviews

Vineyards Paradise

KristineRating, 5 stars2 weeks ago
Our stay at Piero’s home was the highlight of our family’s three week Italy trip! It is one of the most beautiful homes we have stayed at and the spectacular vineyards, gardens, and pool really added something special. We plan to definitely return/stay again! Thank you Piero for sharing your special home!
Superhost
Home in Pievescola
4.93 out of 5 average rating, 106 reviews

Antico Borgo Ripostena – n. 9 Oil Mill

DanielRating, 5 stars2 weeks ago
Martina’s entire estate is very peaceful and extremely beautiful. Just remember that it is really off the beaten path. She was so passionate about the property and making people feel right at home. It was one of the more beautiful places we stayed in all of Italy. Make sure to bring food up there with you before going. It is at least 35 min to town, but this is one of those places it is almost not worth leaving. Wish we had more time to stay there.
Guest favourite
Home in Gaiole in Chianti
4.86 out of 5 average rating, 263 reviews

Charming estate with views

AndrewRating, 5 stars5 days ago
Incredible stay and Bernardino and his family were incredibly welcoming and pleasant. They helped us check in later and were there to help us with any questions we had. Absolutely would recommend to anyone looking for a peaceful Tuscan retreat.
Guest favourite
Home in Lecchi in Chianti
4.96 out of 5 average rating, 136 reviews

Casa di Lyndall - Entire house with exclusive pool

TerriRating, 5 stars7 months ago
This home is the epitome of a classic villa in the chianti region. Lecchi is very a small village that is walkable to a market, bar & cafe, and one of the best dinner spots we visited in our entire trip to Italy - the Malborghetto restaurant is a must! We rented a car for this week of our trip, and would highly recommend doing so. There are many nearby villages with great trattorias and shopping options - and gorgeous views everywhere you turn. Casa di Lyndall is a roomy, well appointed home with all the amenities you could need. Very clean, and very comfortable, and the view out the front windows is beyond compare. Lyndall was very responsive and provided us with excellent recommendations of things to do during our stay. Clementina greeted us when we arrived and was so sweet and helpful. There is nothing we would change about our stay!
Top Guest favourite
Home in Asciano - Chiusure - Monte Oliveto Maggiore
4.96 out of 5 average rating, 182 reviews

Country House in the Crete Senesi

CharlotteRating, 5 stars1 month ago
We feel so lucky to of found Guido and his beautiful house. Firstly Guido could not be more helpful, so responsive, friendly and has the best recommendations! He made sure the house was spotless for our arrival, even the pool is so clean it was perfect. The house itself is stunning, stays lovely and cool in the heat but the garden is just drenched in sunshine. Guido has made sure you can bask in the sunshine by the pool or chill out in shade in the height of the afternoon. There are so many comfortable spots to sit in! The pool was lovely and refreshing when it was hot mid afternoon and looked beautiful in the evening. Tuscany is stunning, there's so much to explore - would heavily recommend a car for that. In walking distance there are a couple of very delicious restaurants and if you're feeling adventurous you can walk to the monostary nearby which is definitely worth visiting. Thank you Guido!
Superhost
Home in Anghiari
4.88 out of 5 average rating, 140 reviews

Tuscan dream in the ancient Tobacco's villa, sauna

JacquelineRating, 5 stars1 month ago
The house is beautiful and unlike anything else. What made the experience amazing was one of the hosts, Daniela. Daniela greeted us upon check in, walked us around the house and went above and beyond and booked us a wine tour where he graciously translated everything in English during the entire experience. Daniela made the place feel like home and I couldn’t recommend him and the experience he provides more.

Weekly house rentals

Guest favourite
Home in Castelmuzio
4.98 out of 5 average rating, 40 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars2 weeks ago
first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!
Guest favourite
Home in Asciano
4.97 out of 5 average rating, 33 reviews

Family Forest - Pool in the Crete Senesi

SylviaRating, 5 stars1 week ago
The area is incredible, peaceful and the view spectacular. Asciano has the delightful charm of an Italian village. The people were friendly and welcoming. Even got greeted by their local police who offered up their number in case we needed anything. I felt safe, and it felt as if I lived there for years. I’d say this is a piece of heaven on earth. Bellezza maestosa! Non vedo l'ora di visitare di nuovo la Toscana e la città di Asciano! Grazie!
Top Guest favourite
Home in Castiglione d'Orcia
4.96 out of 5 average rating, 93 reviews

Da nonna Ornella - nest in Val d'Orcia

AlexanderRating, 5 stars2 days ago
Nice little accommodation in a very nice area, very quiet location. Unfortunately, I only stopped for one night, but it is certainly worth staying longer.
Top Guest favourite
Home in Monticchiello
5 out of 5 average rating, 39 reviews

Lovely home to dream

NadinRating, 5 stars2 weeks ago
Sarah was in touch with us before arrival, recommended restaurants and inform us about the parking place, as you can't park inside the old town. the apartment was as in the pictures, beautiful view
Top Guest favourite
Home in Montalcino
5 out of 5 average rating, 8 reviews

New Palazzo in City Center: 4 King Bedrms 6 Bath

RiteshRating, 5 stars1 month ago
Thank you Brian for sharing your beautiful home with us for a couple of days. Your home is by far the best maintained and most well equipped and pristine places that we have stayed so far. We had the most amazing time in the house as well as walking around the city in the evenings. The location is perfect for everything from shopping to restaurants and wine tastings. Thank you Valentina for taking care of our needs during the stay, we would definitely return to stay at your house the next time when we visit. Thank you so much🙏
Superhost
Home in Montalcino
4.83 out of 5 average rating, 66 reviews

N° 24

가영Rating, 5 stars5 months ago
Such a wonderful place to stay!! The stone house is so pretty. Located at the end of Montalcino, you can enjoy stunning panoramic views from the bedroom and living room. The kitchen was equipped with simple seasonings and kitchen utensils, and it was nice that it was separated from the bedroom and living space. The beautiful living space was perfect for drinking delicious BDM wine! Caution! Be careful not to hit your head on the ceiling when looking out the window!😂
Guest favourite
Home in Montalcino
4.94 out of 5 average rating, 32 reviews

Domus Antiqua

JonathanRating, 5 stars5 months ago
We had an excellent stay at this beautiful home which is very spacious, comfortable and very well furnished. The views are superb even by the high standards of Montalcino. Communication was proactive and very helpful. Nothing to fault. We would definitely stay again and look forward to doing so.
Guest favourite
Home in Poggio San Marco
4.97 out of 5 average rating, 274 reviews

Charming converted Hayloft overlooking the Chianti Hills

StuartRating, 5 stars6 days ago
Leonardo’s place was the stuff Tuscan dreams are made of. When you think of a beautiful authentic Tuscan getaway, this is it! Leonardo was super quick to respond when we had questions. He had left us wine and cheese and helpful information as well. Just FYI -The bedrooms and bathrooms were up a narrow stair case so we just left our suitcases downstairs which worked out fine for us but could be an issue if you have mobility issues. We stayed out in the lounge chairs and hammocks for hours; if you walk down into the olive groves and to the right, you can see the sunset over the incredible Tuscan hills. Our only issue was finding it both times we drove in - the first day, we took a wrong turn and ended up on a one-lane dirt road but miraculously came out on the main road and found it easily from there. Coming home from Siena the next day, we took a different route so then got confused. But these inconveniences were outweighed by everything else. Highly recommend!!

Private house rentals

Top Guest favourite
Home in Castiglion Fiorentino
5 out of 5 average rating, 35 reviews

Hidden gem in Tuscany

MitchellRating, 5 stars3 weeks ago
Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.
Top Guest favourite
Home in Buonconvento
4.97 out of 5 average rating, 87 reviews

S.Ilaria - Private pool Villa with 2 bedrooms

AlisonRating, 5 stars2 weeks ago
Fabulous setting in the middle of fabulous Tuscany. The views from the house were stunning! The farmhouse itself was so charming - every detail. We enjoyed dinners on the covered patio, evening walks on the gravel road through the countryside and lounging by the pool with a glass of red wine. The setting is also the perfect location for day trips to nearby cities. We visited Montalcino, Montepulciano, Siena, Pienza and Cortona. Highly recommend!
Guest favourite
Home in Rocca d'Orcia
4.86 out of 5 average rating, 29 reviews

Casa Primavera a Rocca d'Orcia

AlessandraRating, 5 stars2 weeks ago
I only stayed one day with my partner, but I left my heart in Rocca d'orcia, the Paesino is perfect for a few days of peace and quiet in a setting from another era. The accommodation is spacious, the kitchen is complete with everything, the bedroom is spacious and the bed is comfortable. Near the house, there is a restaurant that offers Tuscan food with a touch of originality. I would say perfect, everything absolutely recommended. I hope to return.
Top Guest favourite
Home in San Giovanni d'Asso
5 out of 5 average rating, 62 reviews

Country chic house in a village,private pool,wiFi

PennyRating, 5 stars3 weeks ago
Lorenzo met us on the street to walk us to the villa and showed us everything with a very warm welcome! The views are breathtaking! We found the location to be an excellent base to visit all of the surrounding towns. Having Grazia Franchini (see the host’s guidebook) prepare and serve dinner for us in the villa after a fabulous day of Brunello wine tastings was such a treat! Would definitely return to the area and stay here again but next time will set aside a day just to relax by the pool!
Top Guest favourite
Home in Pienza
5 out of 5 average rating, 53 reviews

Pienza Center - Stylish Apt, 6 Guests, A/C & WiFi

ShirleyRating, 5 stars2 weeks ago
We loved our stay in this apartment. It was perfect for the three of us - clean and very well stocked for us with extra amenities!!!! We really appreciated that. We love Pienza, and very much enjoyed our stay here. Thank you!!!
Superhost
Home in Lucignano
4.95 out of 5 average rating, 38 reviews

La Casetta

LauraRating, 5 stars1 month ago
Beautiful, peaceful stay. Amazing, secluded location. The hosts were very friendly and welcoming - made us feel right at home. Lots of great walks around, including the nearby winery. The only downside is it does get rather cold in the stone apartment but during warmer weather the coolness in the apartment would probably be perfect. They provided a portable heater & a hot water bottle though which was nice. Thank you Tebea for being such a lovely host!
Superhost
Home in Castelnuovo di Val di Cecina
4.93 out of 5 average rating, 67 reviews

L'Uva Fragolina. House, Garden, Panoramic View

DavidRating, 5 stars2 weeks ago
A Tuscan dream. Some days I had to pinch myself to realise that I wasn't in a movie. My girlfriend and I had a wonderful time in the region and also in the house. It was clean and tidy. The kitchen was unique and we also enjoyed barbecuing outside. We simply enjoyed it and felt at home. Finally, relaxation and tranquility, which you rarely experience. Thank you for your trust in this wonderful piece of Tuscany. A must-see for all those seeking peace and quiet or people who really want to experience what Tuscan flair means. We will be happy to come back!
Guest favourite
Home in San Giovanni d'Asso
4.88 out of 5 average rating, 49 reviews

Ca' Montalcino

AndreaRating, 5 stars1 month ago
Great location to visit the Val d 'Orcia and its villages. Quiet place, courtesy and punctuality from Silvia and the other Silvia who welcomed us:)) House matching the description , clean and well furnished.

Quick stats about house rentals in Montalcino

  • Total rentals

    110 properties

  • Nightly prices starting at

    $61 AUD 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

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Montalcino
  6. House rentals