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

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.

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.

Vineyards Paradise
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!

Podere Tignano, 4-bedroom villa in the Chianti!
How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!

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!

The Owl: view, pool and garden
Ein unvergesslicher Aufenthalt im Herzen der Toskana! Die Wohnung liegt traumhaft schön in der Natur – umgeben von sanften Hügeln, Weinbergen und unzähligen Olivenbäumen, die in der Sonne silbern schimmern und das Landschaftsbild einfach magisch machen. Die Aussicht ins Tal ist atemberaubend schön – man könnte stundenlang einfach nur dastehen und schauen. Der 28 Meter Pool? Besser geht es nicht – perfekt gelegen mit Panoramablick, absoluter Ruhe und einer Atmosphäre, die zur puren Entspannung einlädt. Was diesen Ort aber wirklich besonders macht, sind die Menschen: Jacopo, Sophia und ihre Kinder haben uns mit einer so herzlichen Offenheit empfangen, dass wir uns sofort wie bei guten Freunden gefühlt haben. Es ist einfach schön, solchen Menschen zu begegnen – authentisch, warm und voller Lebensfreude. Und dann war da noch Luba, die Schäferhündin – ein echtes Herz auf vier Pfoten! Sie hat uns jedes Mal mit solcher Freude empfangen, dass wir sie sofort ins Herz geschlossen haben.

Antico Borgo Ripostena – n. 8 Casa Vecchia
This place is something else! The views, the pool, the houses, the interior - it’s something else. We stayed with our 18 month old and had such a happy time - surrounded by nature in such gorgeous accommodation and a kiddy kitchen / toys which were perfect for Otis. It’s simply beautiful and Martina is so helpful - highly recommend with a family or groups of friends for a zen and unique time. Close to lots of gorgeous places and Martina has wonderful recommendations. Only watch out is the 2km dirt track road to get to the location but it’s 100% worth it and quite fun! Enjoy - we can’t wait to come back :)

Romantic cosy flat - Toscana Italy
This air B&B was in a beautiful area of Tuscany with breathtaking views. The property had many areas to sit and enjoy the rolling hills.
Weekly house rentals

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!

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
Apartmán nás skutočne očaril, izby pekné, čisté s klimatizáciou, štýlové, v obývačke veľká Tv, kuchyňa so všetkým čo tu má byť. Samotný "rezort" bol na kopci s krásnymi výhľadmi, obrovská záhrada, bazén, všetko štýlové také Toskánske, okolie prenádherné, pohoda, kľud,pokoj, všetko čo tu potrebujete tak aj nájdete. Ako vravia Taliani, je to tu " Tutto bene"

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!

New Palazzo in City Center: 4 King Bedrms 6 Bath
Palazzo Tamanti ha pienamente soddisfatto tutte le nostre aspettative !! Cercavamo un luogo perfetto e denso di atmosfera per trascorrere un capodanno magico e particolare : quest'anno abbiamo trovato il top !! Abbiamo amato ogni angolo di questa residenza , ristrutturata da poco e dotata di tutti i confort ... Materassi, guanciali, piumoni e imbottiti superlativi !! Non ho mai dormito così bene... A palazzo Tamanti ogni dettaglio è curato al massimo e ogni ospite si sente coccolato dall'inizio alla fine del soggiorno.... Impianto elettrico sopraffine, tutte le dotazioni tecnologiche sono perfettamente funzionanti e di livello elevato, le quasi 200 foto presenti sul sito sono perfettamente rispondenti alla realtà. L'accoglienza da parte dell'host Valentina è stata perfetta, sempre gentile e disponibile. La casa è situata in pieno centro storico , per cui tutto è a portata di mano e si può raggiungere a piedi. Cari Brian, Carrie e Valentina, grazie di tutto !!

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!😂

Bel Casale with sea view and the mediaeval village
Die Kommunikation vor unserer Anreise war sehr gut, die Gastgeberin hat sehr schnell auf Nachrichten reagiert und sich selbst auch proaktiv bei uns gemeldet. Wir wurden sehr freundlich empfangen und durften sogar 1h früher einchecken. Uns wurde alles in und um das Haus gezeigt. Das Haus und der Garten + Pool waren sehr sauber. Die Klimaanlagen in den Schlafzimmern waren wichtig und haben auch gut funktioniert. In der Küche findet man alles was man benötigt. Der Garten ist schön groß und top gepflegt. Auch der große Pool mit dem wunderschönen Ausblick hat uns begeistert. Die Gastgeber, die ca. 50m neben an wohnen, haben sich jeden morgen um den Pool gekümmert und geprüft ob dort alles okay ist. Die Anfahrt war auch relativ einfach. Ca. 30 Minuten Autofahrt zum Haus gibt es einen großen Coop Supermarkt, wo wir einkaufen waren. Das Meer ist auch nur 30 Minuten mit dem Auto entfernt. Alles in allem waren wir sehr zufrieden und haben unseren Urlaub als 6 Personen Gruppe voll genossen!

Domus Antiqua
We loved staying in this beautiful home in Montalcino. It was even more beautiful and unique than the pictures! My family of five loved staying here- lots of space for everyone and it was fun to be right in the 500 year old town. We especially love having coffee and wine on the balcony.
Private house rentals

Casolare immerso nella natura
Stayed here last week for 5 days. On arrival we were met with a welcome basket of food a bottle of wine a bottle of homemade olive oil and also bottles of water on arrival. The pictures don’t do it justice it felt like a place out of a fairytale, the property is surrounded by tons of olive trees and greenery. If you want a quiet relaxing holiday this is place to go. Rosella was amazing with quick responses and extremely welcoming, we are definitely going again next year.

Wonderful country house
We had a brilliant week at Jakob and Margit’s house. Margit was so friendly and helpful (and gave us some wine and fresh eggs!). The views from the gardens are incredible and having the swimming pool was perfect. The local area has lots of great vineyards to visit and the house is close to Florence/Siena/Arezzo for day trips. It had everything we needed like a washing machine etc.

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.

Casa San Ripa: Relax Oasis with Private Pool
We had an amazing time in Casa San Ripa. The house is even nicer than it looks in the pictures, the view is amazing and the outside area is lovely, with all the lights in the trees at night. The whole property was very clean, including the inside and the pool, the instructions were easy and Giulia is super responsive and extremaly nice and helpful. We had a great stay and would highly recommend!

La Casetta
Wir hatten eine wirklich wunderbare Zeit in der Unterkunft! Sie ist genauso wie auf den Fotos: Sehr schön eingerichtet, ruhig und mit tollem Ausblick. Eines der schönsten Airbnbs, in denen wir bisher waren! Der Pool war leider geschlossen, dafür kann man aber in den umliegenden Seen schwimmen gehen. Wir waren nur zwei Nächte dort, wollen aber ganz sicher noch einmal wiederkommen und dann auch länger bleiben!

L'Uva Fragolina. House, Garden, Panoramic View
Ein Toskanischer Traum. An manchen Tagen musste ich mich kneifen um zu begreifen das ich nicht in einem Film bin. Meine Freundin und ich haben eine wunderbare Zeit in der Region und auch im Haus gehabt. Es war sauber und ordentlich. Die Küche war einzigartig und wir haben gerne auch draußen gegrillt. Wir haben es einfach genossen und uns wie zuhause gefühlt. Endlich mal Entspannung und Ruhe, die man nur noch selten erlebt. Vielen Dank für das Vertrauen über dieses wunderbare Stückchen Toskana. Für alle Ruhe suchenden oder Menschen die wirklich erleben wollen was Toskanischer Flair bedeutet ein Pflichtziel. Wir kommen gerne wieder!

Ca' Montalcino
Posizione ottima per visitare la val d’orcia e i suoi borghi. Luogo tranquillo, cortesia e puntualità da parte di Silvia e dell’altra Silvia che ci accolto :)) Casa corrispondente alla descrizione , pulita e arredata bene.

La finestra - centro storico Montepulciano
Paola’s place is very quiet and comfortable with spectacular views. Her apartment is a short walk to the center of town and the public parking area. Paola ’s communication was very good, from providing videos to show where to park, restaurant recommendations (and help with reservations) and regularly checking in on us. Highly recommended!
Quick stats about house rentals in Montalcino
Total rentals
110 properties
Nightly prices starting at
G$8,363 GYD 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
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Tenuta Le Velette
- CavallinoMatto
- Pubblico Palace
- Castiglion del Bosco Winery
- Golf Club Toscana
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Podere La Marronaia, Sosta alle Colonne
- Cantina de' Ricci
- Riva del Marchese
- Cantina Contucci
- Madonna del Latte
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