Family-friendly vacation rentals in Pienza

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!

Authentic Tuscan countryside experience, with amazing views and excellent facilities. Well located if you want to explore all that Tuscany has to offer.

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 responded very quickly and helped us. To just get out and enjoy the nature and tranquility of Tuscany, it is perfect. We will be happy to come back!

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.

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!

We can absolutely recommend it! Everything is as described in the text and seen in the photos. Located about 2 km outside the totally cute village of Casole de Elsa. Andrea + Barbara provided all the necessary information about the arrival and many great local tips, always with the corresponding links. For example, our arrival was delayed due to traffic to about 10:15 pm. Was no problem, we were in contact and when we arrived, Andrea personally welcomed us. And if we had a question during our stay, an answer always came very quickly. (Where to park in Siena, how to get to Florence, ...)

Great central location. Close to everything. Space is spread out so your tripping over your other guests

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

Stefania was super nice to wait for us despite we were later for 3 hours. Her house was very beautiful and lots of space for 10 of us. Everyone can have their own space on the balcony or terrace. Can have BBQ too. House was very well equipped with everything that we expected. Had a wonderful time. Thank you.

Great house, stayed here for four days. We don't have a car, so we can only choose a place with convenient transportation.It's closer to the train station and has a beautiful view. It's the best place for us! The host was very friendly and picked us up and dropped us off at the train station. Friends without a car can book a day tour, or rent an e-bike/electric car to get around. The room on the second floor has a great view. You can see the beautiful Tuscan countryside when you open the window. The natural scenery is accompanied by birdsong. The whole person is quieted, it's really cozy. There is a kitchen, you can buy cooking supplies at the nearby supermarket and cook your own meals (30 minutes walk). The room is clean and tidy, the bed is moderately soft, everything is very satisfactory.The only regret is that the pool doesn't open until May. I hope I can come back next time!

We were welcomed by Sabrina's dad. He's a very nice man. He even shows us the way to the grocery store. The accommodation is very clean with lots of amenities. And what about the view is quite beautiful. This is a place to stay that I would recommend without hesitation. Thanks to Sabrina and her family.

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 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!

Anna Rita's place was even more beautiful than the pictures and in a great location. Anna Rita's sister, Lucia met us when we arrived. She gave us a tour, explaining how everything works. The space was large and welcoming. The outside terrace was especially beautiful and a peaceful place to unwind. The upstairs master suite was extraordinary. It was comfortable, quiet, spacious and had a balcony overlooking the terrace. The only downside was that the downstairs bedroom could get quite loud due to the adjacent restaurant on the other side of the wall. Our host was always very responsive. We will definitely return!

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.

We had a wonderful time in this fantastically located apartment! The house is wonderfully quiet with a Tuscan postcard view – especially at the pool, a real highlight. After a small start-hopala (not that bad and quickly clarified) we got exactly the apartment we had booked – and it absolutely matched the description. The hosts were super warm, helpful and always trying to make our stay as comfortable as possible. We especially enjoyed the optional Italian breakfast – delicious, lovingly made and with a lot of charm. Perfect location for exploring the surrounding area, from small villages to larger cities, everything was easily accessible. A great place to relax and enjoy – we will be happy to come back!

We had an amazing four weeks staying at Bellagatta, using it as a base to explore Tuscany & surrounds, and it met all our expectations and more. Bellagatta is a positioned on a hilltop with stunning 360 degree panoramic views, more beautiful than the photos. The annexe that we stayed in was exceptionally clean and comfortable and well fitted out. Air con was useful on the first few days of our stay which were very hot. The property is well situated, 10 minute drive into Buonconvento (not quite an easy return walk up the hill!) which was convenient for restaurants & shopping. Gaetano was a most delightful host, very welcoming, & always taking interest in which towns we were travelling to and providing useful tips for our visits. His property manager, Susil, was also readily available and looked after us with anything we needed , even providing fresh eggs, vegetables & olive oil from the property. Highly recommended!

We had a great time at Clarissa and Antonio's cottage which is in a beautiful and quiet location but close to the center of the village of Radicofani. You can walk there and there are small shops and good restaurants. The cottage is well-equipped, clean and very nice. We were greeted by Sara and Marcello who are very friendly and very nice. We really enjoyed the small welcoming touches. The cottage is in a very good location geographically for visiting the main villages of Tuscany and enjoying beautiful landscapes. We were able to enjoy the pool at the end of the stay which was very nice. We would happily stay at Clarissa and Antonio's again.

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 have now stayed in 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 unwind 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!

Giorgia has really created a paradise there and we are very happy that she shares this beautiful place with guests. Unfortunately, we could only enjoy the cottage for 3 days and would definitely like to come back. The house is small but very well furnished, the mattresses very cozy and water comes out of the shower with proper pressure - which is not quite a matter of course. The house is a bit off the beaten path, but thanks to Giorgia's really great videos, it's very easy to find. The garden (or rather small park) around the house is very well maintained and we were able to pick cherries and mulberries. Much has already been written about the pool - it really is THE highlight. An absolute recommendation - thank you Giorgia!

Andrea’s house is one of my favorite Airbnb’s ever. The setting is gorgeous - sitting outside with coffee in the morning was a highlight for me. The house is even better than the pictures, the pool lovely, and both Andrea and Ramona were extremely helpful with recommendations and responsive to questions. It truly felt like being a welcome guest in someone’s home.