Vacation rentals with breakfast in Montepulciano

I immediately fell in love with the charming flowery facade and decorated with a whole bunch of little curiosities ☺️ I also loved the romantic bedroom with the wrought iron bed and the classic style wardrobe. Lovely! And Deborah is very available. Thanks to her.

We loved our one night stay here. Riccardo was a great host! A perfect place to stay with everything we needed and the beds were super comfortable and so quiet. A fantastic small town to visit. Would definitely stay here again and recommend.

Lorenzo was an exceptional host. Very attentive, thoughtful, and full of great local recommendations. He checked in regularly to ensure we had everything we needed. If I could rate this place 15/10, I would! We had a rental car, and the location couldn’t have been better, just a 10-minute drive to everything, with convenient parking right in front of the house. Plus, the garden was absolutely stunning

My friends & I spent 5 days at Il Casone in May, and what a delight it was. The Villa is both isolated and a short drive to various levels of towns and shops, cafes, and restaurants as needed. And of course a well equipped kitchen to cater for yourself. We were met by Roberta, the hosts father, and had a wonderful introduction and tour of the garden, the history and stories of the house and area, eventually we were allowed inside! It was a great welcome and Roberto was a good help to us many times we had questions the Villa is nicely renovated, farmhouse style and has everything you need it is very clean and good for people, like me, who might have mobility issues as it is all on one level and has wall in showers. While there we did a full day tour of the Chianti region which was great. They picked us up at the Villa and we visited two places to taste and also had lunch - do this! We loved our rural Idyll and would recommend Matteo’s Villa enthusiastically! Thanks Matteo & Robert

I don’t have the words to describe how beautiful this apartment on the hillside is. The apartment itself is nice and cosy and spacious, and the kitchen contains a little bottle of olive oil produced from their own olives. But it is the location, the gardens and the little farm and the view across the valley which can take your breath away. Sonia is happy and welcoming and patient. She showed us around the wine and olive farm and was always approachable when we contacted her. There are two guest apartments side by side, but it is quite private nonetheless. Note that you can hear sounds from the other apartment quite easily. I cannot recommend this enough! Would love to come back.

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!

Great stay and great host!

We arrived later than expected due to a delayed flight and I couldn't find my directions for parking. I phoned Lorenzo who came and found us and took us to the apartment. Because of the time there was no where that we could get something to eat so he brought us snacks to keep us going until the morning. There where items that we could have for breakfast already provided. We found its location for getting to all the major cities ideal, either by the train service which was close ,and not expensive (15.20 euros ) for 2 return tickets to Florence , or by car. Pisa , Lavorno, Lucca and Sienna all around an hours .drive. Silvia was always helpful and did not impose herself on us unless we needed help. This was our first time in Italy and it was a very pleasant time .We would use again if we returned to this area without hesitation.

Massimo place was wonderful for our stay, very quite place and close everything. Thank you Massimo for your help, you're great host 👍

Filippo’s space was even better in person. Fairy lights over the bed greeted me upon arrival. I had coffee and tea as well as some brioche for my mornings. The room is beautiful, loved the painted walls. The bed was comfortable and despite the heat outside, it was cool inside.

Caterina’s place was immaculate. She welcomed us and showed us how to use everything and chatted to us about the area. The linen was clean, bathroom was spotless and all the smaller details were provided. I highly recommend this home for someone traveling to Florence. Thank you so much and we will be back!!!!

Clara was responsive and helpful. She was there to meet us and help us with parking and walked us through the entire house. She was wonderful. The space was perfect with a wonderful patio. Totally would recommend.

Easy check in and out. Beautiful space and much bigger than expected. Great place to relax and explore if staying in the city. Really no negatives, book it and be happy.

I had a happy time in a house that looked like it was in a movie in a beautiful natural environment. I think I will keep my time in Kian Tti as a good memory thanks to the kind and friendly host who responds so quickly. It was a little difficult at first for the city girls who were new to the road to the accommodation, but it wasn't difficult when they got used to it. It's perfect for watching the sunrise and sunset. I left today, but I want to go again.

Filippo's place is definitely one of the best Airbnb's to know the Toscana. Filippo, in the first place, was very flexible with the check-in hour, allowing us to make the check-in around 6 pm after we visited San Gimigniano and Certaldo. Filippo's apartment is strategically located if you want to visit San Gimignano/Certaldo/Siena (25 minutes away by car). And the rest of the beautiful towns of Tuscany as Montepulciano/Montalcino/Val D'Orcia/etc...are only 1 hour away by car. The surroundings of Poggibonsi are beautiful, and the town is really relaxed and full of excellent options to eat (eating information provided by Filippo). To resume, this place is outstanding and has everything you need to have a wonderful time under Tuscany's sun and landscapes. The apartment has a dishwasher, a clothes washing machine, and it's really big. If you want to visit Tuscany, this is definitely your place. Thank you, Filippo, for being a wonderful host.

We stayed here for three nights. The location is great for visiting the historic center of Arezzo on foot and the area is really very quiet. Being the historic center, you have to park outside because of the ZTL (active at certain times and days) but in 5/10 minutes on foot there are parking areas. Great starting point also for visiting the surroundings, Val di Chiana and Val Tiberina.

My husband and I had the most incredible stay at Francesca’s B&B! Not an exaggeration that this is the most beautiful place I have ever been. Historic and authentic, with modern updates. The rooftop terrace is absolutely breathtaking and a great spot to watch the sunset over the vineyards. There are several restaurants right next door to the b&b, Divino, osteria di passignano, and Scuderia, all are fantastic and the osteria has a well deserved Michelin star. Breakfast was served every morning where you have a table reserved for your stay. Francesca was very friendly and responsive if we needed anything at all. We will absolutely be back!!

If you looking for a peaceful and beautiful house this is your place. The view from the balcony is amazing. Annalisa is friendly and responsive host! I definitely recommend the place!

The style, the cleanliness, the scent of my grandma's home. Really a caress after a day on a motorbike. Super breakfast with homemade tarts. Lots of availability from the owners but with the right confidentiality. I'll be back

We absolutely loved our stay at Serena’s! Beautiful location, fantastic views and a lovely host. Serena was very accommodating and we felt right at home (plus her dinners and breakfasts were delicious!). Would definitely love to come back!

Staying with Matteo and his family was such a pleasure. Don’t miss out on dinner, Matteo is a fantastic cook and the view from the terrace is unbeatable. I took a beautiful hike straight from the house, and they were super flexible about picking me up from the train station. It was the perfect oasis after the bustle of Firenze. Thanks for everything! Hope to be back soon!

Our stay was truly unforgettable. From the moment we arrived, we were welcomed with such warmth and kindness. It felt like visiting family. The hosts are the most genuine, thoughtful couple we've ever met. Their hospitality went far beyond anything we expected. They were incredibly responsive and offered fantastic recommendations for the area, but what really made our experience special was the cooking class we did with them. We learned how to make fresh pasta and dessert from scratch, then shared the most delicious meal together. It wasn’t just a dinner,it was a memory we’ll carry with us forever. Out of our entire 19-day trip through Italy, this was hands down the highlight. The property itself is straight out of a movie. The home is stunning, filled with character and charm, and the grounds are peaceful, beautifully maintained, and truly capture the magic of Tuscany. If you're looking for an authentic, heartfelt experience that goes beyond just a place to stay, this is it!!

This was our second stay here and couldn’t have been happier. The family that runs Agri. Casanova de Pescille are responsive, caring and just a delight to be around. Highly recommend anyone wanting to peaceful and relaxing place to stay with access to the many small towns in Toscana consider staying here. Grazie.

Maurizio is a very kind and respectful host. He is incredibly knowledgeable about the art and history of Florence and enjoys sharing his passion. The breakfast was delicious and we enjoyed the wonderful Italian coffee each morning. Thank you Maurizio.