Family-friendly holiday rentals in Montalcino

If I could move in here permanently, I would. What a gorgeous stay with responsive and respectful hosts. Everything was as described, the hot tub was glorious, and we loved looking through the binder of photos of painstaking restoration over the years.

Incredible trip. Paola and Michele were so friendly and welcoming. Always there to give advice and make sure you had everything you needed. The little converted hay barn was just beautiful and lovely. Location wise it just couldn’t be beaten. The garden was amazing and we ate outside morning and night, easy access to amazing Tuscany countryside and also a short trip on the train to Florence from Montevarchi. Loved every minute we were there and we were sorry to leave. Would highly recommend.

We had a wonderful week in Gloria's house. Our four-legged friend also felt totally comfortable in nature. The house is small but nice and has everything you need. The property is a nice size and is perfect for eating outside, relaxing in the hot tub or just lying in the sun. The way to the house is a little challenging, but with a normal car and a little driving experience it can be mastered. Gloria was always available to us and gave us good excursion tips for the area in advance. Even with any inquiries, she always reacted very quickly and helped us. It is perfect for simply getting out and enjoying the nature and tranquility of Tuscany. We will be happy to come back!

We just checked out of this wonderful villa today, and it has truly been one of the most special places we’ve ever stayed. We arrived with my husband’s parents, my husband, and our toddler, and from the moment we got there, everything exceeded our expectations. Alex greeted us warmly, gave us a tour of the villa and the property, and provided detailed printed information about nearby restaurants, supermarkets, cafés, bakeries, and wine tours. The property also produces its own wine, which was available for purchase and could be conveniently delivered to our villa during our stay. Alex shared his contact number and made himself available in case we needed anything—which we really appreciated. One of the highlights of the property was the stunning infinity pool overlooking the vineyard and offering breathtaking views. It was the perfect setting to disconnect and truly live in the moment. The air conditioning and hot water worked perfectly. Thank you Alex!

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.

If you stay here, you will find yourself in a painting, so beautiful is this cottage located in the mountains! Lucca is really super nice and funny. He tells a lot. The restaurant they run is fine too, and good food! The breakfast is very good. We definitely recommend this cottage!

Very nice stay for a few days relaxing in summer. Beautiful olive gardens around the house, nice collection of wine. Everything clear, super big house, will come back next year!

Chiusi may not be a major hilltop town but it is very special because it lacks the tourists. We had plenty of restaurants to visit in the week we stayed, and lots of historic sights to see. You do need a car to visit surrounding towns but the peacefulness of Chiusi makes it delightful. Rafaels place is perfect with the balcony and sublime views. He was an exceptional host who did not impose on our privacy but always friendly and helpful. I would highly recommend this place and town.

Wow, what a beautiful apartment this was. Nestled in the countryside by the Tuscany/Umbria border is this gorgeous farmhouse owned by Simona and Yens and what a find it was! The rolling hills are captivating and if you want to switch off, enjoy visiting beautiful villages, eat lovely food and really rest, this is the place to do it. We were welcomed by their two friendly dogs and received lots of tips about the local area from Yens on arrival. The apartment is spacious and serene. From spending evenings on the patio eating al fresco, watching the stars or having morning swims, we had a wonderful time and would wholeheartedly recommend this to anyone and everyone seeking some peace and quiet. The farmhouse is remote but it's very easy to get anywhere by car and the drives are never dull with the countryside views. It's hard to put into words how relaxing this place is and so I suggest you book and find out, you won't regret it! Thank you so much Simona and Yens!

We had an amazing stay! Very nice and warm people and cute dogs. Fantastic view, green and lush garden. Delicious food and drinks. Fun with pasta course! Recommend this place! Fantastic experience!

We were immediately enchanted by this property. Everything here makes up the image that one can have of the beautiful Tuscan countryside. At the top of the hill overlooking the valley, the view is splendid and romantic. The property has been renovated with today's comforts while retaining its soul of yesteryear. You feel good right away, the energy is beneficial, nature, animals, everything is in harmony! The welcome, Oscar's cooking, the superb pool, the shaded terrace, the hearty homemade breakfasts! It's more than a favorite, this place is a gem! We'll be back!

Beautiful place, everything ready with refreshments, accommodation quiet and clean ... Air conditioning functional, but almost not needed, because it was a beautiful classic Tuscan accommodation, where we definitely were not the last

Very comfortable accommodations and gorgeous property and views

We come from Hong Kong, and a building like this is not often seen there. We are very happy to have had the chance to stay at the house. Some of the details in the house really impressed us, especially the antique furniture! Pietro is a great host—very friendly and responsive. I had some pleasant conversations with him. Thanks again!

I truly enjoyed my stay here! The place was clean, cozy, and exactly as shown in the photos. The best part was the host – so kind, warm, and welcoming! They made sure I had everything I needed and were always just a message away. 😊 Just something to note for future guests: the house is quite remote and up a hill, with no nearby neighbors. It can feel a little quiet. if you're not used to that kind of setting. But if you're looking for peace, privacy, and a break from the busy world, this is the perfect escape. Overall, a lovely stay with a wonderful host. Thank you so much for everything! 🌟

We loved our stay here. It is a beautiful home and a beautiful space. The only thing I would note for future travelers is the host speaks Italian and not much English. Communication prior to check-in was a little slow but ultimately very smooth. The host met us when we arrived and was very nice. Would 100% stay here again.

We had a great stay in Clarissa and Antonio's cottage which is located in a beautiful and quiet place but close to the center of the village of Radicofani. You can walk there and find small shops and good restaurants. The cottage is well-equipped, clean and very pleasant. We were greeted by Sara and Marcello who are very friendly and very nice. We really appreciated the little welcome touches. The cottage is very well located geographically to visit the main villages of Tuscany and enjoy beautiful landscapes. We were able to enjoy the pool at the end of the stay, which was very nice. We will be happy to stay with Clarissa and Antonio again.

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!

Giuliani is a wonderful host who made us feel as if this slice of paradise was our home, too. The location, the meticulously restored home, the views all make for the ultimate Tuscan experience. But Giuliani and her husband bring it all together with their warmth and attentiveness. It was a tough place to say goodbye to — for now. If you are looking for a Tuscan experience, this is it. And remember to ask for the hosts’ home-cooked meal. It is a culinary experience in the very best sense.

An incredible, beautiful house where you’ll feel right at home. The villa is spacious and welcoming, perfect for cooking and relaxing with friends. My only suggestions would be the need for fans in the bedrooms as without AC it gets quite warm during those hot evenings.

We had a great stay! Simona welcomed us warmly and showed us everything in peace. The Airbnb is beautifully situated in the middle of nature – perfect for unwinding and unwinding. The place was very clean, lovingly and cozily. We felt completely comfortable and would come back anytime. Thank you for the wonderful time!

We have now been to Elisa and Alessandro's accommodation for the second time – and it was simply beautiful and absolutely relaxing again! The place is a real oasis where you can switch off perfectly. Elisa and Alessandro are extremely helpful and warm. They provided us with great tips for activities and restaurants, so we could enjoy our stay all around. We'd love to come back and highly recommend this place!

A very peaceful retreat in a beautiful garden with lots of private places to sit or eat and an extended view over the valley towards Arezzo and mountains beyond. Caroline was helpful but did not intrude. The cottage has an authentic Tuscan style and furniture to match and although quite dark there are big windows looking out onto the garden and view. We enjoyed using the private pool and exploring the local area as well as a National Park to the north (lovely beech forest) and Siena. The TV isn’t ‘smart’ and there is no dishwasher but this is reflected in the price (however there’s a large book collection including lots of guidebooks). It was a very relaxing stay for us, thank you.

Simple amazing stay to discover Tuscany and even stay in to relax. Giulio is always present for any help without being intrusive. The house and grounds are well taken care of while keeping an amazing Tuscan rustic vibe. We made amazing family memories and can’t recommend it enough to anyone looking for a central stay to explore the best Tuscany has to offer.