Family-friendly vacation rentals in Montalcino

Gina’s place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.

Cannot recommend more highly. A fantastic experience from start to finish. Helpful from the moment we booked to the moment left, including helping us organise lunches and wine tours. The villa itself is spectacular with stunning views of the Tuscan countryside. The villa was clean, spacious and charming with a bathroom for every room, fully equipped kitchen, games room, TV room and laundry. The pool is fantastic, as is the hot tub and the outdoor dining area and BBQ was perfect for everyone to eat, drink and laugh around. A truly memorable holiday at an unforgettable place

Alex, u show such hospitality to our family!! We love how well u maintained the place. The view from our hotel brings smile to my face every morning! It’s spectacular. I’ll definitely come back! Hope the price is reasonable the next time 🥰

What a fantastic find!! Bernadino and Edoardo were superb hosts at the beautiful house overlooking the vineyards. It had all the amenities you could wish for and was spotlessly clean. Edoardo cooked for us one evening and it was so delicious and reasonably priced. I would gladly have had her cook for us every evening!! A perfect stay, couldn’t have asked for more 😊

A peaceful and relaxing stay in the beautiful countryside. The unit is private & gorgeously renovated & bedroom overlooks vineyard. The hosts- Andrea & his brother were very welcoming, helpful and friendly, with lots of local suggestions. The main villa tour is also amazing. All in all a wonderful stay! Thank you!

Our stay at Riccardo & Kate's property was fantastic, the property is as described, the views were awesome. Riccardo was more than happy to help us with local recommendations & bookings when we needed help as we speak next to no Italian. The local town of Castell'Azzara is a beautiful place & the local people were very helpful at the Coop, bakery & restaurants.

We had the most incredible time at Cristina’s place! Her home is so beautiful, and surroundings are so picturesque! We enjoyed a cooking class with Cristina’s husband Carmelo and it was an incredible evening! She was so friendly and responsive. I hope one day we will be able to return to this incredible spot in Simignano!

Very nice and clean appartment in a very quiet area. Only Met Gaston shortly since we were out all day visiting Tuscany with friends, But he was very Friendly. Will definitely come back

We were six adults, two children (3-year-olds) and one infant staying at the house for a week. It’s located in a secluded spot with a large garden and beautiful views of the Tuscan landscape. We used all of the five bedrooms upstairs and they were dark and cool. The kitchen and living room downstairs also stayed cool. Right outside the kitchen there’s a really nice spot that’s in the shade for the most part of the day, where we had most of our meals. This is a great place to relax and enjoy a dip in the pool. However, you definitely need a car to get around. The gardener came around several times a day to maintain the pool etc. We appreciated this, but might be good to know if you’re looking for complete privacy. We also had some issues with the bathrooms; one toilet and a shower didn’t work properly but were fixed within a day and this didn’t affect our experience. The washing machine didn’t work despite repeated attempts by the host to fix it. The barbecue is in the trash room.

Marina's place is one of the most beautiful places I've ever seen. The attention to details, the amenities and her communication made our stay very relaxing and enjoyable. Thanks Martina for a great stay in Tuscany.

We had an incredible stay at Clara's property in Cortona! The highlight of our trip was definitely the visit to the farm, which was not only fun but also deeply meaningful. We loved learning about the local way of life. Our host, Clara, was warm, welcoming, and extremely helpful throughout our stay. They went above and beyond to ensure we felt at home and had everything we needed. The property itself was clean, comfortable and well-located. We would highly recommend to anyone looking for an authentic and unforgettable experience in Cortona. Grazie mille, Clara for sharing your little slice of heaven with us!

We loved our stay at Giulia’s - it was like home from home and had everything we needed. It has beautiful surroundings and is great for cycling! Giulia was very helpful with recommendations and friendly too.

We've been guests to six people. When we arrived in the evening, the apartment was as described, well heated and comfortable The staff is courteous, kind and always available. We had dinner in their restaurant, high quality cuisine at affordable prices. Repeat experience

A truly stunning place with incredibly welcoming hosts. The villa exceeded our expectations in every way. The interior is filled with beautiful historic furniture, details, paintings, and books. The cozy fireplace in the living room added a special charm. We loved making pizza in our very own wood-fired oven, using the outdoor BBQ, and dining al fresco surrounded by breathtaking views. Every moment at Poggio del Fattore felt special, offering the perfect blend of comfort and authenticity. Highly recommended for anyone looking to experience the beauty of the Tuscan countryside in style!

The only thing I could say negative is the lack of lighting for the kitchen and dining room. For the rest everything is perfect if you like the countryside decor:-)

Lucia and her husband are wonderful hosts, warm and kind-hearted. Their home is truly magical—clean, spacious, and cozy. We felt so welcomed and comfortable throughout our stay. Highly recommended!

Heidi's apartment is situated in a larger complex on the outskirts of the village, just a short walk from the town center where you can find a church, a mini supermarket, bars, and a popular restaurant that is always fully booked. The village is ideally located in the heart of Chianti, making it a perfect starting point for exploring the region. You can drive along one of the scenic, winding roads to a wine tasting event, enjoy a bike ride through the picturesque countryside, or visit nearby cities like Siena or Florence (Firenze). One of the highlights of the apartment is the spacious swimming pool (1.35 m deep), which is perfect for cooling off during the hot summer days, especially if you have kids. The apartment itself is well-equipped, ensuring a comfortable stay. Communication with Heidi is easy and friendly. She provides detailed information on the check-in and check-out procedures, as well as instructions for using various amenities in the complex. We enjoyed our stay!

The villa exceeded our expectations. It was exceptionally clean and well cared for. Excellent amenities. Beautiful surroundings with olive and lemon trees. Cute little village nearby with an excellent restaurant. The host was very responsive. We had a bit of trouble finding the place but that might be more us than the directions. You definitely need a rental car Thank you for an amazing stay

Nice agriturismo, very chill place and beautiful surroundings

Thank you for allowing us to stay at your wonderful accommodation. This was the best place to celebrate my 50th birthday. What wonderful accommodation, facilities and the surrounds of Tuscany. Thank you for your lovely hospitality and making us feel so welcome. Roxy

Fantastic accommodation with lovely views of the countryside. Especially loved the fire place and large spacious kitchen. Charley and Ann were very gracious hosts and I would have no problem recommending this accommodation to anyone who wants to visit Tuscany. The accommodation was within 30 mins of most tourist towns and trains which made it excellent for day trips.

Gorgeous stay! Views were stunning and the villa exceeded expectations. This was a perfect place to unwind and relax. Highly recommend.

Paula has not only created a beautiful sanctuary that perfectly reflects Tuscan culture, but offers wine tasting and a vineyard tour on her property. The location of this gem of a place is centrally located in the Chianti region , making it a perfect home base for day trips to Assisi, Firenze and nearby small villages that offer great restaurants and quaint shops. The region is cycling friendly, as well as offering places for day hikes. Staying here for five days was one of highlights of our Italian adventure.....and we highly recommend experiencing the perfect place to stay in Tuscany and the warmth and friendliness that Paula, Ferderico and her staff offer!!

The house was large and roomy and each room had a private bath with a good shower. The kitchen was well equipped. The hostess was extraordinarily generous with the little things she made available to us. We might have wanted to grill for a dinner but the outdoor grill was rather greasy and not appealing to use. The one drawback ( that was not her fault) was the horrible condition of the road leading to the house. All in all, a great stay.