Family-friendly holiday rentals in Pienza

Our stay was a dream to be in. Francesca and Francesco have created a wonderful place, are likeable people and great hosts. We were warmly welcomed and received all the necessary information. From the first moment, we felt at home and were able to freely explore the lovingly designed grounds and also enjoy them in privacy. The contact with other guests was also pleasant and respectful. The rooms are rustic and tastefully furnished and exude a special charm. The view will take your breath away. The journey to Poderracio is correspondingly adventurous (switchbacks and narrow, bumpy road). All products, such as the breakfast basket, are super delicious and of high quality. In addition, we received freshly harvested vegetables (zucchini, beetroot, onions and garlic) from Francesca. During the stay, we were invited to bake pizza together in the private rooms and enjoyed a wonderful evening. THANKS!

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.

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.

I can not say enough about Alessandra and her amazing land! It was the most magical place we have ever been to. We are taking a 3 month trip, hitting up 21 cities in Europe and this is BY far the best! She was so kind and took us shopping and back to our train! She was always there when we needed her.thank you Alessandra we will see you next year!

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.

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!

Great flat to explore Cortona! Excellent location and had everything you need

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!

What tranquility and what a view. Beautiful estate and super friendly people who try to make you feel comfortable. Also a nice and pleasant swimming pool for when it is very hot.

We had an amazing week long stay!! Sabrina is a fantastic host! The apartment was SO clean and comfortable and had everything we needed. Breakfast each morning was very yummy and fresh! We did the dinner one night and it was so amazing! Location is great too. Easy drive to many close by towns, grocery stores, and restaurants. The property is beautiful with lots of flowers. A little too cold for the pool during our stay but our kids loved the swing set and teeter totter. Absolutely recommend staying here!

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 loved staying here. A breakfast is included and it was wonderful. We attended the cooking class at the last minute and it was fabulous! Nicola was very good about communicating during the whole process.

Wonderful place for a family and to recharge in our busy trip to Italy. Sign up for the farm to table experience when you stay. The hosts could not have been more helpful and wonderful. Beautiful property and accommodation.

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.

We had the most magical stay at this Tuscany farm! The property is absolutely stunning — nestled among rolling vineyards and olive groves, with postcard-perfect views in every direction. Our apartment was spacious, charming, and had everything we needed for a comfortable stay. The hosts were incredibly kind and welcoming, sharing local recommendations. Our kids loved meeting the animals, exploring the grounds, and especially swimming in the beautiful pool overlooking the hills — it was a total dream! Evenings on the terrace with a glass of wine and the Tuscan sunset were unforgettable. This was a once-in-a-lifetime experience for our family, and we can't wait to return. Highly recommend to anyone looking for a peaceful, authentic Tuscan escape! 🌿🍷☀️

This was such an amazing stay! Very quiet, peaceful, and relaxing stay far away from the major cities. Beautiful views from everywhere! Would recommend doing their wine tour on site. It was fun, informative, and delicious! You definitely will need a car to get to this place in addition to restaurants and grocery stores. Would highly recommend this place!

We had such a lovely stay at Paolo's place in Montepulciano! The location was beautiful and the pool was a highlight! They also had a little playground which was great for our toddler. Paolo was very welcoming and gave great recommendations for places to eat. They grow olive trees on the property, so they provided a little bottle of homemade olive oil in the kitchen, which was delicious! Thanks for having us and we hope to come back in the future!

Perfect Tuscan getaway. My wife and I absolutely loved our stay and were blown away by the accommodations. The apartment was extremely spacious with a living room, bedroom, kitchen and bathroom. The pool onsite was spectacular. Wine tasting and lunch onsite as well. We were even given a delicious bottle of Chianti Classico (~$45 value) upon arrival. Highly recommend!

Il Villino Farmhouse is a wonderful place to stay in Tuscany. Its location is convenient to many adjacent towns allowing for great day trips exploring Tuscany. Liza and Daniella couldn’t have been more helpful. Liza arranged for groceries to be delivered prior to our arrival as well as a private Chef to make dinner our first night. What a special treat that was. The grounds are well cared for and offer a lot of outdoor seating options for the unit we stayed in. You won’t be disappointed staying at this lovely property.

Liliana, was a brilliant sweet host. Extremely helpful and kind. She has a beautiful super friendly dog, who loves attention! The property was in such a lovely location, stunning views and so peaceful. The apartment was cosy and had everything you need. I would recommended staying here. We had a lovely stay!