
House holiday 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

Cercis - La Palmierina
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!

A Charming House in Asciano - Siena
Very nice place with a great view, very quiet and relaxing. The apartment was clean and cozy. The only inconvenience were the squeaky doors.

Private villa/swimming pool in Tuscany
Everything was absolutely perfect! ⭐️ Location: Ideal base for exploring Tuscany — you’re right in the heart of it all. Whether you’re heading to Florence, Pisa, or the charming hill towns, everything is within easy reach. House: Well-equipped and comfortable, with all the listed amenities in perfect working order. After long days of sightseeing, the pool was a refreshing retreat. The panoramic view over the valley is truly breathtaking. Host: Lorenzo is an outstanding host — friendly, responsive, and fluent in English. He was proactive and helpful throughout our stay. The house includes a detailed guidebook he created with handpicked recommendations for local shops, markets, restaurants, farms, and sights. It made planning our days effortless. Bottom line: If this listing is available — don’t hesitate. Book it. 10/10 would recommend!

Country House in the Crete Senesi
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!

Casa di Lyndall - Entire house with exclusive pool
Yet another fabulous stay! Thank you Lyndall for sharing your special space. Getting in on the village pizza night was a surprise bonus and so fantastic to enjoy the local community. Until next time :)

Gaiole in Chianti Poggio Casabianca
Valeria und Simone haben eine super schöne und saubere Wohnung! Wir haben uns von Anfang an sehr wohlgefühlt. Die Wohnung bietet einen super Ausgangspunkt für zahlreiche Wanderungen und Ausflüge. Während unseres Aufenthaltes haben wir immer gute Tipps und Ratschläge von den beiden bekommen. Unser Hund hat sich auch sehr wohlgefühlt und da das Grundstück komplett eingezäunt ist, konnte er sich frei bewegen. Wir würden jederzeit wiederkommen. Es war eine unglaublich schöne Zeit!

House Rigomagno Siena
Wir hatten eine wunderbare Zeit in diesem absolut niedlichen Haus, das inmitten atemberaubender Natur liegt. Die Ruhe ist einzigartig – man hört nur das Zwitschern der Vögel, und hin und wieder zeigen sich Rehe am Waldrand. Einfach magisch! Der Pool war top gepflegt und man hatte richtig Ruhe. Ein echtes Highlight war für uns die Küche: So liebevoll eingerichtet und außergewöhnlich gut ausgestattet – das haben wir so noch nie erlebt! Der Gasherd und der hochwertige Backofen haben das Kochen zu einem Vergnügen gemacht. Gastgeber Diego war unglaublich freundlich, aufmerksam und herzlich. Man fühlt sich bei ihm sofort willkommen und bestens umsorgt. Ein perfekter Rückzugsort für alle, die Natur, Ruhe und liebevolle Details zu schätzen wissen.

Tuscan dream in the ancient Tobacco's villa, sauna
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

Casa Ora d"Oro - Panoramic Views
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!

Family Forest - Piscina nelle Crete Senesi
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!

Da nonna Ornella - nido in Val d’Orcia
의사소통이 약간 아쉬운것 빼곤(이것도 번역기를 통해서 의사소통 가능)정말 최고의 숙소였습니다 위치부터 호스트까지 모두 만점을 드리고 싶어요 환상적인 풍경과 따뜻하고 배려심 넘치는 상냥한 디바가 있어서 우리의 허니문이 완벽했습니다 너무 멀지만 기회가 된다면 꼭 다시 오고 싶습니다 우리에게 최고의 경험을 선사해준 디바에게 존경과 감사와 경의를 표합니다 당신은 정말 최고에요, 디바!

Casa Primavera a Rocca d'Orcia
Ho soggiornato solo un giorno con il mio compagno, ma ho lasciato il cuore a Rocca d’orcia , il Paesino è perfetto per restare qualche giorno in tranquillità in un contesto di altri tempi. L’alloggio è spazioso, la cucina completa di tutto, camera spaziosa e letto comodo. Vicino a casa c’è un ristorante che offre cibo toscano con un tocco di originalità. Direi perfetto tutto assolutamente da consigliare. Spero di ritornarci.

Graziosa abitazione per sognare
This place is definitely a piece of Tuscany Italy. it will always hold a special place in my wife's and my heart with how beautiful and amazing the house was and the town it is located in. it seemed very well located, close to hot springs, multiple other cities, beautiful country side with horse back riding, world class winery's, ect. She is a great host and I would highly recommend this Airbnb to anybody looking for a one of a kind experience in Italy.

Country chic house in a village,private pool,wiFi
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!

N° 24
너무나 멋진 숙소!! 돌로 만들어진 집이 너무 이뻐요. 몬탈치노 끝에 위치해있어 멋진 파노라마 경치를 침실및 거실에서 감상할 수 있어요. 주방에는 간단한 조미료와 주방기구들이 구비되어있고 침실 및 생활공간과 분리되어 있어 좋았어요. 아름다운 거실공간은 맛있는 BDM와인을 마시기에 완벽했어요! 주의할 점! 창밖을 볼때 천장에 머리를 부딪히지 않게 조심하세요!😂

Tosco Suite "Solis"
Wir haben unseren Aufenthalt in der Unterkunft sehr genossen! Der Ort und die Umgebung waren traumhaft schön – wir haben uns rundum wohlgefühlt. Der Gastgeber war äußerst freundlich und herzlich, was den Aufenthalt noch angenehmer gemacht hat. Besonders der Ausblick vom Balkon war atemberaubend und der Whirlpool ein absolutes Highlight! Wir können diese Unterkunft auf jedenfall weiterempfehlen und kommen gerne wieder. 😊
Private house rentals

Hidden gem in Tuscany
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.

S.Ilaria - Private pool Villa with 2 bedrooms
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!

soggiorno in Val d'Orcia
Wir hatten eine sehr schöne Zeit bei Giacomo. Die Gegend ist wunderschön und wir konnten durch Giacomos Empfehlungen alles mit einem geliehen E-Bike erkunden. Das Restaurant im Ort war ein Traum, da sind wir durch Giacomos Empfehlung hin. War alles super!

Il nido del Rondone
You will not regret your stay! From the moment we were greeted by Elisa’s father on arrival we felt welcomed. The accomodation exceeded our expectations with absolutely everything that you would need with the bonus of being able to access to the amazing pool. It is only a short walk down to the city centre. To top this all off, the hosts are extremely generous and friendly. Thank you for sharing your little piece of paradise with us. We will look at returning one day!

Casa Ilda A/C, Wi-Fi Private parking
Excelente, mas o aluguel é só da parte de cima, tem que subir as escadas, mas não atrapalhou nada.

Noi 2 Vacanze in Fortino d'Amore
This was a wonderful space with amazing history of the Val d'Orcia. Giuseppe was a delight showing us everything we needed to know in this very well appointed two story unit. The bed was extremely comfortable and the hosts went to great lengths to supply everything we could need, especially the Illy coffee and moka pot for espresso. Having the clothes washer was a big plus. The views from every window are breathtaking and the location is a perfect balance of feeling out in the country while close to tourism sites. Have a car was very useful. The unit sits amongst many making it feel like a little quaint and quiet town with a small grocery steps away. We were very fortunate to have found this place and would recommend to anyone as something very special and quietly romantic.

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

La Casetta
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!
Quick stats about house rentals in Montalcino
Total rentals
110 properties
Nightly prices starting at
$67 NZD 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
- Gulf of Baratti
- Cala Violina
- Marina di Grosseto beach
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Cavallino Matto
- Cala Di Forno
- Santa Maria della Scala
- Casa Barthel
- Tenuta Le Velette
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- CavallinoMatto
- Pubblico Palace
- Castiglion del Bosco Winery
- Golf Club Toscana
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Cantina de' Ricci
- Podere La Marronaia, Sosta alle Colonne
- Riva del Marchese
- Madonna del Latte
- Cantina Contucci
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