House vacation rentals in Radda in Chianti

We had a brilliant week at Jakob and Margit’s house. Margit was so friendly and helpful (and gave us some wine and fresh eggs!). The views from the gardens are incredible and having the swimming pool was perfect. The local area has lots of great vineyards to visit and the house is close to Florence/Siena/Arezzo for day trips. It had everything we needed like a washing machine etc.

Everything was absolutely perfect! ⭐️ Location: Ideal base for exploring Tuscany — you’re right in the heart of it all. Whether you’re heading to Florence, Pisa, or the charming hill towns, everything is within easy reach. House: Well-equipped and comfortable, with all the listed amenities in perfect working order. After long days of sightseeing, the pool was a refreshing retreat. The panoramic view over the valley is truly breathtaking. Host: Lorenzo is an outstanding host — friendly, responsive, and fluent in English. He was proactive and helpful throughout our stay. The house includes a detailed guidebook he created with handpicked recommendations for local shops, markets, restaurants, farms, and sights. It made planning our days effortless. Bottom line: If this listing is available — don’t hesitate. Book it. 10/10 would recommend!

How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!

Sonia was extremely helpful from start to beginning. Gave us great recommendations which ended up being some of our favourite nights! The most stunning location and beautifully kept place, with everything you could possibly need to live in. 30 mins from Florence, 1 hour from Siena and miles of beautiful scenery and wineries as far as the eye can see As a british couple in our 20’s we loved our stay here ❤️

We stayed 5 amazing days at Il Gufo and loved every minute. Jacopo is an amazing host and went out of his way throughout to make our stay great. Even meeting us locally and showing us the way to the house. We highly recommend staying at The Owl. The location, high in a valley provides spectacular views and is perfect to relax and unwind. We do not know what was better. The location, accommodations or the fact that we met Jacopo and became immediate friends. That combination made for the greatest memories. Also Luba, their beautiful dog, immediately loved us and greeted us ever time we returned. A little secret, he is an amazing chef and if you get a chance to go to his restaurant do it. Also his dinner recommendations were great. We had dinner at Corte Dei Frati 2 times. Thank you Jacopo for making our 30th Anniversary trip so amazing. We feel privileged to have met you and we will return on our next trip to Italy. You are an amazing person and host. Love Steve & Vicki

Very good stay at Giulia's. Pleasant and spacious house. Good location for discovering Chianti and its white roads.

We thoroughly enjoyed the stay. Everything was very clean. Such a great environment. We traveled with a 1-year-old child and were very warmly received. For my daughter, there were many toys, a crawling blanket, baby bed and high chair. The small playground was also impressive. Our highlight was the great sunset and of course the most beautiful pool we have experienced so far. We can only recommend it!

The house is beautiful and unlike anything else. What made the experience amazing was one of the hosts, Daniela. Daniela greeted us upon check in, walked us around the house and went above and beyond and booked us a wine tour where he graciously translated everything in English during the entire experience. Daniela made the place feel like home and I couldn’t recommend him and the experience he provides more.

This is our second summer spent staying here and we absolutely love it. The private garden provides the feel of being in the countryside but you are 5 minutes (if that) from the city center of Radda.

The area is incredible, peaceful and the view spectacular. Asciano has the delightful charm of an Italian village. The people were friendly and welcoming. Even got greeted by their local police who offered up their number in case we needed anything. I felt safe, and it felt as if I lived there for years. I’d say this is a piece of heaven on earth. Bellezza maestosa! Non vedo l'ora di visitare di nuovo la Toscana e la città di Asciano! Grazie!

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 everything we needed for a very relaxing stay in rural Tuscany, away from the hustle and bustle of daily life. Our hosts, Alejandra and Filippo, were very welcoming, friendly and helpful with local recommendations.

What a magical, unforgettable place to stay! The home is the perfect size for two, and we felt right at home. It’s very clean with plenty of towels, blankets, pillows, and cooking appliances. We really enjoyed waking up to the sound of birds singing and having breakfast on the patio before making excursions to Siena, Florence, Poppi, or nearby Rufina. The neighbor’s cats also greeted us home when we returned (very lovingly!). Would absolutely love to stay again!

Beautiful and peaceful location nestled between olive trees and vineyards, right in the heart of nature. A perfect spot to relax and enjoy scenic walks through the surrounding hills. It's about a 45–50 minute walk down to Greve, and the charming medieval village of Montefioralle is also within walking distance, with a small but nice selection of restaurants. The apartment is well equipped, with fans in the main rooms and a functional, fully stocked kitchen. The garden and outdoor area are a real highlight too - especially the lovely terrace, perfect for dining and relaxing. But the true highlight of our stay were Tamara & Luciano! We've rarely met such warm and welcoming hosts. From the very beginning, they made us feel at home, greeted us with open arms, treated us with homemade culinary touches, and were always available if we needed anything. We felt completely at ease and would love to come back anytime.

The stay was like a fairytale – I highly recommend this place. We can’t wait to come back!

This was our second time staying here and we'd love to return again some day. The location is very convenient and the courtyard has a fantastic view. Sonia and Carolina are extremely kind and helpful.

Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.

We had a beautiful stay at Alessandro’s property. The property is in the middle of the Tuscan hills with gorgeous views on all sides and feels very undisturbed and untouched. We were super lucky to have the place to ourselves the whole time and felt totally at peace. The apartment was beautiful and incredibly spacious with everything we needed, with lots of space in the grounds to go for walks and sit outside and enjoy the views and weather. Panzano is only a 7 minute drive away for supermarkets (small Co-op and village shop etc) and restaurants, and Alessandro was very responsive when we had any questions or if we needed anything. We couldn’t have been happier and will definitely be back next year!

first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!

We had a great stay in la Casina! The view from the garden is just what you expect from Tuscany and the place is ideal for a calm and relaxing stay. The kitchen is well-equipped and there are a lot of nice extras to explore (the vinyl collection, a guitar etc.). Edoardo had lots of good suggestions for the area and was great host! Highly recommended :)

one of my best experiences! Leonardo is an exceptional host, kind, considerate, smiling (even when we arrive much later than expected!!) his advice was very valuable to us. the accommodation, the region and the environment are very pleasant If we were to come back to Tuscany, I wouldn't hesitate for a second to come back and I'm already recommending it to my friends!!

One of the best places we've stayed and he explained why: Monia and her daughter Giusy were very kind, good hosts and respond quickly. We loved the place: perfect to disconnect and spend time surrounded by nature in a large, clean and comfortable house. In addition, the house was very well stocked, especially the kitchen: they left us many things for breakfast and also for dinner, which was enough for more than one day without having to go shopping at the supermarket! Also as parents we really appreciate that the crib for our baby was wooden, with its mattress and everything, like at home. It wasn't a travel crib, so it turned out to be super comfortable for our baby. They also had a changing table and high chair, which were great for us. In a future opportunity, we will surely repeat!

Best part of our Italy trip! We loved our stay at Casa Marinella, and Monica has thought of every detail to make for a wonderful and peaceful vacation! Relax by the pool and enjoy breathtaking views. Be sure to stop by Gelateria di Castellina for a scoop of cremino gelato and try the fiorentina steak at Osteria La Sosta di Pio VII.

The house is very spacious and beautifully decorated. We especially enjoyed the yard, the pool, treehouse and the walks on property with a beautiful Tuscany view. Giada was a great host, offering area recommendations and helped to book reservations. Upon arrival she made us her homemade spaghetti sauce, baked goods, fresh fruit and provided all the ingredients for us to feel at home the first night. This was so appreciated!