Apartment vacation rentals in Radda in Chianti

5 Stars – A Tuscan Dream Come True! Our stay at Francesco’s private resort-style retreat in the hills of Tuscany was absolutely magical. The location is stunning—peaceful, picturesque, and the perfect escape into the beauty of the Italian countryside. The rustic room had so much charm and comfort, and the property itself was amazing, with not one but two beautiful pools to relax by. One of the highlights was the on-site restaurant. The free breakfast was far beyond the typical offering—not just muffins, but a full, authentic Italian breakfast that we looked forward to each morning. Dinner was just as impressive, showcasing delicious local flavors and warm hospitality. It was also a great jumping-off point for exploring the region—we took a lovely day trip to Siena with ease. This place is a hidden gem, and we’d return in a heartbeat. Highly recommended for anyone looking to experience the best of Tuscany!

Incredibly tranquil, set in the Italian countryside. The property had everything we needed. Ana was also very responsive whenever we needed anything.

Laura and Stefania were fantastic hosts and the apartment was the perfect base to explore Castellina in Chianti and the Tuscan hills. They were both very responsive and friendly and had suggestions for places to eat as well as helped plan local transport.

Best place to stay!!! The charm of property draws you in immediately! A lovely garden, fresh flowers in the apartment, stunning views of San Gimignano. We loved the touches of old Italy everywhere (with the subtle inclusion of modern flair). And the little extras - a beautiful homemade tart welcomed us, as well as fresh fruit, juices, coffee and creamers and a few more fun surprises! Fabio and Alessandra are fabulous hosts - always answering any of our questions and having excellent advice on where to eat and things to do! The location is perfect for day trips to many of the Tuscan and Chianti region towns. And so lovely to come back to the charm of Fabio and Alessandra’s place. Grazie mille!!!

AMAZING stay. More beautiful than the photos. Spotless. 5 min drive to Siena. View of the wine country. Bed was more comfortable than my bed at home. Owner was extremely friendly and helpful.

We originally planned to stay at Bryan’s place over the weekend just to explore nearby Florence, but the charm of his home completely stole the show. Florence felt like the cherry on top instead of the other way around. Nestled in a huge, lush garden bursting with hundreds of flowers and all kinds of trees, and staying in a cozy apartment that felt like a little museum, we had such a wonderful, memorable experience that left us feeling truly happy. Bryan was not only super friendly and easy to talk to, but also incredibly welcoming and helpful. Next time we’re in Florence or any nearby town, there’s no question - we’ll be coming back here!

Our stay at Casavecchia in Tuscany was the highlight of our European trip so far. What a wonderful experience! Mario’s villa was a beautiful, peaceful, escape from the hustle and bustle of Florence. We ate at the restaurant for lunch and dinner, and loved Federico’s authentic food. A full buffet breakfast each morning was included, making our stay even greater value for money. Iona was so friendly and gave us many great walking tips, as we didn’t have a car. Federico also kindly drove us to the local train station when we left (which we were sad to do!) Thank-you all for your wonderful hospitality. We will definitely recommend your place to all, and hope to return one day.

Highly recommend anyone new to Italy to try San gimigano first. Staying here allowed us flexibility to explore other cities and had plenty of great spots in walking distance. Lorenzo provided fantastic recommendations and assisted with everything we asked for.

Worth every penny. Elisa was helpful and responsive. Very very convenient to check in and out. Beautiful view of the piazza and large patio. The photos actually don’t do it justice. The furniture has been updated since the photos and the whole apartment is clean and renovated. She left us a bottle of wine and waters in the fridge. We felt right at home in the heart of Chianti. The Greve market is on Saturday and mostly clothes but fun to watch and walk through. Many restaurants and places to go to. We would definitely stay here again.

You will literally be in History, that is, in a 13th-century castle: there are some drawbacks (such as the rather steep access staircase), but the accommodation is cozy, warm and comfortable (especially if the weather is rainy outside, as during our stay) and the view of the surrounding valley is a real spectacle, especially in the early hours of the morning. In the immediate vicinity of the accommodation there are shops and clubs, which is definitely positive, since the village of Volpaia is about a 10-minute drive from the center of Radda in Chianti. Alessandro (assisted by Loriana) was an exemplary host in all respects.

Very nice apartment. We visited a real palace. Frescoes create a special Italian atmosphere. I liked everything very much.

The place was very great. The room was decorated with many luxurious stuff, made us feel like we are staying at a 5-star hotel. They were also many snacks and food in the kitchen for free. Elena was also very kind and helpful during the whole stay. Location wise it is a bit far from some tourist attractions in Tuscany, but if you have a car you will not have a huge problem. And finally I suggest you spare some time of yours in the morning to enjoy the view of the house.

The stay at Tommaso's farm house was perfect! I would even so it was the highlight of our visit to Tuscany 🙌 Great location near Castellina in Chianti, which made it easy to pick up supplies and visit places nearby. The swimming pool and the view were also just perfect to hang out and relax. Recommend reading the check-in instructions before you get there so you check-in at the right place in town 😅 That was our small mistake, but the people at the hotel check-in were super friendly and helpful. Can totally see us coming back again. Thanks for such an amazing stay!

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!

Spectacular view. Relaxing after a long trip thru wineries. Town was very cute and comfortable

Great condo in a lovely Tuscan town. Located within walking distance of a lovely and lively main square as well as the train station with good connections to other towns in Tuscany. We had a great stay here

Paola is a great host! Everything was clean and perfect and the view was breathtaking! I 100% recommend!

Luca’s apartment overlooking the piazza was absolutely perfect! There were reviews about it being loud but honestly we were so tired every night from enjoying the beauty of Florence that I didn’t even notice any noise. The location couldn’t have been any better & it was a perfect space for my husband and I. Thank you Luca!!

Superb spot close to river. Bed is confortable. Yes, stairs could be a challenge for some only it is clearly stated. At the end of the day, it’s alright!

We had a wonderful stay. The patio and hot tub were amazing. Walk to everything. No need for a car. Lots of restaurants and attractions close by. Grocery store around the corner. Outdoor hot tub was lovely after a day of steps.

This property is beautiful, clean, convenient, full of modern amenities, and within walking distance of everything a tourist wants to see in Florence. It is nearly perfect in every way. The view of the Ponte Vecchio Bridge is world class. One note: it advertises that it has a hot tub, but it does not.

After another Airbnb mishap, Gianluca was so accommodating to allow to book and check in late last minute. He even met us there personally to be sure we got in okay. He even had the fold out couch ready with linens and provided a few breakfast items. The place was better than we’d hoped, location was fantastic, updated and perfectly clean! We would absolutely stay here again. This place will be one of the highlights of our trip!

We loved staying here and had the most fantastic time. They were super helpful and responsive to everything and we can’t wait to go back.

Martina's place was a great rental in central Florence. Close enough to walk to major landmarks and the central train station. The place has everything you need and more. We were met by Martina and her friendly dog on arrival. She is very friendly and hospitable and took her time to show us her home and give us lots of information on the area and suggestions. I would recommend this rental to everyone!