Family-friendly holiday rentals in Radicondoli

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 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.

We had a really good time at this place. It was spacious, clean, and worked perfectly for our group. There were plenty of bathrooms, and the house had all the amenities you might need for a comfortable stay. The outdoor space was a big plus—especially the terrace and patio area with the big table, which was great for hanging out and having meals together. The location is honestly perfect—super peaceful, but just a short drive to Florence, great local restaurants, and vineyards. Also, there was tons of parking space, which made things super easy for us. Check-in was smooth and the host was really helpful. Would definitely stay here again.

The accommodation is in a large family building perched on a hill and offers a splendid view of the Tuscan landscape. The interior matches the photos perfectly. We find many trinkets, paintings, souvenirs of all kinds that evoke the generations that have succeeded each other in this beautiful house. The pool is exceptionally large and perfect after a day of discovery. Too bad there's no air conditioning, but Antiionetta provided 2 welcome fans. The car can be parked in the courtyard.

Staying at Salvatore’s place was peaceful, stunningly beautiful, and such a natural escape ! We loved the hikes, outdoor spaces, vineyard and wildlife. The air smelled of flowers… just so lovely ! You will need a car to visit nearby villages and the property is rural. Such a special place and the best part was Salvatore’s stories and hospitality ! Highly recommend for a natural escape.

Wow-10 days spent at Alec's villa and could have stayed longer! The age and beauty of this place makes you feel transported back in time. From the stone walls, the detailed wall paintings, furniture and decor, to the solid doors easily hundreds of years old... We spent hours just speaking of it's history. The house is clean, spacious, and had plenty of room for our family of 8. It is situated on a small family vineyard at the top of an incredibly windey road. There outdoor space was safe/secluded for my kids. The hill made for wonderful beautiful views and sunrise. However, as with much of Tuscany, we were glad our rental cars weren't too big! The closest town is 5 minutes away and has a few restaurants... Though not somewhere you can have coffee or walk the streets. About 15 minutes away is San Casciano where you can find coffee shops, restaurants, stores etc. Alec is a perfect host... helpful, responsive, and answered dozens of questions weekly. Book dinner at A Casa Mia for sure!

Staying at Agrigreen La Lama was hands down the best Airbnb experience I’ve ever had. From the moment we arrived, Rita welcomed us with such warmth and hospitality that we felt at home. The property is peaceful, beautifully maintained, and full of charm—surrounded by nature and the kind of quiet that soothes the soul. One of the most memorable parts of our stay was getting to cook in Rita’s own home, which she generously opened to us. It was such a unique and personal experience that made us feel truly connected to the space and the spirit of the farm. If you’re looking for a place to slow down, feel grounded, and enjoy genuine hospitality, Rita’s space is an absolute gem. I’m already looking forward to the day I can return.

Christine and John were the best hosts, making this incredible location even more enjoyable. They went above and beyond, recommending restaurants, wineries and experiences that made our trip unforgettable. Christine also helped us get our lost luggage back, ringing the airport for us and liaising with a driver in Florence to pick it up and drop it off to us. Incredible service. Absolutely recommend!

My wife, brother-in-law, and I had an incredible time in Montepulciano, and Giacomo’s apartment was the perfect place from where we started out daily adventures, took afternoon naps, and then headed out for fantastic dinners. Giacomo’s apartment was excellent, making it easy to get settled after a long day of travel. Giacomo guided us into the temporary parking spot when we got lost for a few minutes, and was quick to assist with any questions we had during our stay. The restaurant recommendations were all excellent, as well as the other activities he suggested. We will definitely stay here again when we visit Montepulciano!

Our stay at Mario's more than met our expectations. We were superbly received with our faithful 4-legged companion. Mario, Anna and all their families are very welcoming and happy to welcome us in this charming building, very quiet and relaxing, we enjoyed the green area and the proximity of the activities detailed by our host (a great thing, the ballet of fireflies in the evening). To conclude, thank you Mario & Co for the discovery of your superb region. Pascaline, Anthony, and Vickie

Super recommended! Flavia welcomed us in a very friendly and kind way, she gave us tips for great restaurants. The house is cozy, clean and is in a spectacular and very quiet location. We'll be back!

This is a lovely and cozy place to stay when visiting Tuscany. It’s very convenient, and I really appreciated the warm welcome and thoughtful hospitality. The room was comfortable, and the garden was absolutely beautiful. Thank you for a wonderful stay!

Our stay was incredible. We had 3 nights, & it still didn’t feel like enough time to explore everything the region of Chianti had to offer. The space is massive & private, with incredible views over the Tuscan hills, so good you don’t want to leave at sunset. I would say hiring a car is almost mandatory to allow you to explore the region. Location is perfect to explore the region. We did the cooking class with Bernardo & it was fantastic. Having done other classes before, this is what they should all be like. Thorough, educational and not rushed! Plenty of time to enjoy the local wines before preparing the most tasty of all the meals we’ve had so far in Italy (that’s not an exaggeration even compared to fancy €40 plates at restaurants). Bernardo & Marta were beautiful, helpful welcoming & respectful hosts. If you’re into pottery, Marta has some incredible work, we wish we had space to purchase more. Bernardo’s local & food knowledge is second to none. Strongly recommend. Thank you!

We spent a week with Aleksandra in Montalcino in the heart of Brunello, a breathtakingly beautiful area. The large property is fantastic and with the tranquility and the view just the right thing to relax and unwind. An unforgettable experience for the whole family. This is how you imagine a Tuscan holiday. We highly recommend the place.

We thoroughly enjoyed our stay. It is a private, enclosed complex in beautiful surroundings. We had a wonderful view of the Tuscan countryside from the terrace. The apartment was very nicely and functionally furnished, very clean and very well equipped with everything one might need for a stay. The accommodation has access to a large swimming pool. There are many interesting places for short trips in the surrounding area. We had a very relaxing stay and will definitely want to return soon.

Great location and friendly hosts!

We had a wonderful stay at Luca’s beautiful place in Tuscany! The location is peaceful and picturesque, perfect for relaxing and enjoying the stunning surroundings. The pool was a highlight – clean, well-maintained, and with incredible views. Luca was a fantastic host – warm, welcoming, and always available if we needed anything. One of the best surprises was his homemade olive oil – absolutely delicious and a true taste of Tuscany. We even took some bottles home! We would definitely love to come back. Highly recommended!

Perfect location - could not select a more beautiful setting. Il Paluffo manages to feel luxurious and green as well as rustic with modern comforts all at the same time. The location is stunning - pictures do not do it justice. Il Paluffo is tastefully decorated, intimate with lots of amenities, and unique offerings. There was a cooking class offered while we were there! This is a truly unique and magical place, the perfect Tuscany experience.

Odina was the perfect spot to relax. Beautiful and comfortable accommodation, wonderful dinners and great communication. Would definitely recommend Odina to people wanting to get away from the city and relax in the countryside.

Valeria and Simone have a super nice and clean apartment! We felt very comfortable right from the beginning. The apartment offers a great starting point for numerous hikes and excursions. During our stay, we always received good tips and advice from the two. Our dog also felt very comfortable and since the property is completely fenced, he could move freely. We would come back. It was an incredibly beautiful time!

We absolutely loved our stay at this property in Reggello! The hosts were so warm and communicative—they greeted us upon arrival and gave us a full walkthrough of the home! The view was stunning, and the pool was beautiful and very clean. Aldo even came by each morning to clean it before we used it, which was such a thoughtful touch. Everything in the house worked perfectly—the Wi-Fi was fast, all the appliances and lighting functioned well, and we had no issues during our stay. The drive from Florence was easy (we had a rental car), and it made exploring nearby wineries and towns super convenient. We also LOVED their on-site farmers market. It was their own personal setup with wines, olive oil, jams, and other homemade goods -- plus fresh produce like eggs, garlic, artichoke, & shallots, which they generously offered free of charge. We’d definitely stay here again and highly recommend this property to anyone looking for a peaceful and scenic escape in the Tuscan countryside!