
House holiday rentals in Montepulciano
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Top-rated house rentals in Montepulciano
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House rentals with a pool

Interno Italiano
What a wonderful experience! The description of the home was excelled by the reality. It was very clean and tastefully decorated — Anna has an eye for design and art. the three bedrooms easily accommodated us. The large patio with its charming table and vine screened roof was a charming place to enjoy our morning cappuccino. the home is situated in a agricultural community built in 1788, situated in extensive vineyards. The buildings have been thoroughly renovated into a series of private homes. The community contained renters like us, but also young communities and older retirees. We had a chance to get to know people in the neighborhood, who were uniformly friendly. the AirBnB is about 25 minutes away from Arezzo by car. The best place to park we found was in the short term parking at the train station. From there it was just a short walk to the Old Town. Anna was a wonderful and charming host. We recommend this property highly!

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!

Antico Borgo Ripostena – n. 9 Frantoio
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.

Charming estate with views
Nous avons adoré notre séjour chez Bernardino ! Le paysage est magnifique, l’endroit est très propre et la piscine est un vrai plus pour se détendre. Bernardino est un hôte attentionné, toujours à l’écoute et prêt à aider à tout moment. Merci pour cette belle expérience !

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.

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!

Romantic cosy flat - Toscana Italy
Norma was an absolute treasure, and her home and family were lovely. The property sits overlooking a lovely castle and a beautiful church with great views on the other side. The property has a great pool with plenty of privacy or interaction with the family, I only wish I spoke more Italian to be able to sit and chat with her lovely in-laws! Norma offered great recommendations for day trips, and overall the local area was great to explore. My only advice would be the usual: rent a smaller car to make life easier! Sitting on the patio overlooking the castle, with a glass of wine, is a memory we will never forget, and is highly recommended. Whether during the day or after the sun has gone down and the fireflies comes out (weather permitting) it's a Tuscan treat you won't want to miss. We truly felt like a part of the family and would love to return to her home the next time we come back. Truly a wonderful experience!
Weekly 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.

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!

La casa nel Borgo - Appartamento Superior Toscana
Marco’s place is in the heart of Montichiello village, perched atop a hill with beautiful views. We stayed one night during our biking trip from Siena and wished we could have stayed longer! Marco is a kind and thoughtful host. The apartment is clean, stylish, and comfortable, with spotless bathrooms and a great shower. The kitchen is well-equipped and includes a cozy table for meals. Air conditioning and a ceiling fan keep the space cool in summer. The apartment is on the first floor, reached by stairs lined with flower pots, and features a charming bookshelf at the entrance. On the ground floor, there’s a storage room where we safely stored our bikes alongside Marco’s. It also has a washing machine and dryer available. A local grocery store is just 300 meters away. Highly recommended for a pleasant stay in this lovely village!

Podere Piazza casa con vista panoramica
Can’t say enough about how great this house was! The views! The house is absolutely adorable! From a story book! Outdoor space was incredible! Loved making dinner in the kitchen (kinda made from local market which Sophia recommended which was amazing! I wish I could stay there for a week!!!

Amazing Cott. in the heart of Siena
Great location only 2 minutes walk from the Cathedral. Accommodation is airy and well equipped with its own lovely garden giving you a great place to relax so close to the centre. Francesca was always available and made us feel very welcome. Have already recommended this property to our friends.

the birds view
Asunto oli mahtavalla paikalla. Auringonlaskut on porautuneet ikuisiksi ajoiksi verkkokalvolle :) Upea näkymä! Helppo kävellä kaikkiin Montepulcianon ravintoloihin ja muihin kohteisiin.

Charming house in Cortona, Tuscany
Our family stayed for 4 nights and we absolutely loved it! Great location close to fantastic restaurants and entertainment in the square. Ester’s home is cozy and quaint.
Private house rentals

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 di Mela
We loved our visit at the accommodation! Beautiful city, lovely flat, great area. Very clean and nice to live in, the benches in front are perfect for concluding the evening with a glass of vino nobile di montepulciano. Modern stove and kitchen allow for easy cooking, always a blast. 5/5.0

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!

Beach House, sulle rive del Lago Trasimeno
Para valorar esta propiedad, hay que empezar por el ANFITRIÓN, un profesional en toda regla. Desde el minuto 0 de la reserva, hasta la salida; siempre atento, muy amable y muy profesional. Es un placer conocer gente seria y esto la da un valor a la aplicación. La beach house, es un paraíso en Italia. Fácil acceso, cuidado al detalle, paz, naturaleza, comodidad. Nuestro viaje era en familia con nuestros dos caniches y creo que fueron los que más disfrutaron de la propiedad, verlos correr y saltar por las zonas verdes de la propiedad y convivir con muchas aves, conejos no tiene precio. Nuestra hija disfrutó su estancia estudiando y con la paz y tranquilidad del lugar, no le costó nada concentrarse. Nosotros en cambio, hicimos turismo por la zona, todo muy cerca y bien comunicado por carretera. Es una propiedad muy cuidada, segura y sobretodo disfrutar de sus puesta de sol, sentado en una tumbona, disfrutando de un buen vino (de la zona) es una experiencia irrepetible. Gracias Maurizio.

Hortus Conclusus House
Apartment was centrally located in the town. Very walkable to shops and restaurants. Beautiful sunrises through bedroom window. Very responsive hosts, especially with getting to the apartment from the train station (no Uber or taxi services when we arrived, so my advice is to get off at the previous stop if coming from Florence or make advance taxi arrangements). The hosts were very helpful and called their go-to cab driver. Beautiful with town and can’t wait to return!

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!

Stunning Tuscany Villa in Montepulciano
We had a wonderful stay! The location was perfect. We especially enjoyed the flexibility to use the kitchen for cooking after much eating out and lived mornings and evenings on the roof top terrace!

Casina boutique con piscina riservata ai 2 ospiti
Where to begin? We had the most glorious stay at Fernando’s wonderful home. Genuinely, best holiday we have ever had and we will definitely be returning! Firstly, Fernando and his family were incredibly kind and hospitable! Fernando checked us in, gave us an overview of the wonderful villa (which is even more stunning in person!) and had left olive oil, pasta, cheese, wine etc. All the necessities! He treated us to a tour of the property on the penultimate evening, and his mother made us a traditional Tuscan dinner of meats, cheese, etc. The aperitif was delicious! Fernando’s lovely wife also spoiled us with homemade limoncello. Wow! We did not expect this and were pleasantly surprised! I hope we can repay the favour somehow someday. The property itself is stunning. You can tell that Fernando and his family invest a lot of love and energy into the place. If you’re looking for a break in paradise, go here! Thank you Fernando and family!
Quick stats about house rentals in Montepulciano
Total rentals
50 properties
Nightly prices starting at
$84 NZD before taxes and fees
Total number of reviews
2.1K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Lake Trasimeno
- Lake Bolsena
- Marina di Grosseto beach
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Cala Di Forno
- Santa Maria della Scala
- Terme Dei Papi
- Basilica of St Francis
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Tenuta Le Velette
- Pubblico Palace
- Castiglion del Bosco Winery
- Mount Subasio
- Cantina Colle Ciocco
- Golf Club Toscana
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Podere La Marronaia, Sosta alle Colonne
- Cantina de' Ricci
- Cantina Contucci
- Madonna del Latte
- Abbey of Monte Oliveto Maggiore
- Podere Il Cocco
- Poggio Talamonaccio