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!

We spend here 4 nights with our dog and felt right at home. I love nature and I love to cook and the kitchen being small has everything and a window on the Tuscan landscape, Considering we were not lucky with the weather Antonio gave us a few great tips what to do and we had an amazing time! Also special shoutout to sweet Tilda ❤️ we miss her already John Olya Floyd

We had an unforgettable time here - the nature as well as the complex itself are beautiful, a bit rustic with a few renovations, about which Ana can tell a lot. You can spread out on the grounds, have enough privacy if desired and can watch the most beautiful sunsets. The pool between the olive trees is also fantastic. We were able to visit some cities such as Florence and Siena from here, and here Ana had great tips for suitable restaurants. We will be happy to come back!

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.

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.

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!

An unforgettable experience at Agriturismo Casavecchia – the heart of Tuscany! If you are looking for the real Tuscan feeling, then Agriturismo Casavecchia is an absolute gem. Located in a breathtakingly beautiful area, surrounded by rolling hills, cypresses and vineyards, it feels like you have landed in a postcard. What really makes this place special is the people. The hospitality is heartwarming – sincere kindness, as if you were staying with family. You immediately feel welcome and comfortable here. But the absolute highlight? The restaurant. Every evening is a culinary experience. Authentic Tuscan dishes, prepared with fresh ingredients from the region and prepared with love. The flavors are pure and intense, and every meal is a feast. Whether you enjoy a traditional pasta, a grilled piece of meat, or a local wine, everything is right. In short: Casavecchia is not just a stay, it is an experience that will stay with you. For those who really want to experience Tuscany

We had a lovely stay at Liza and Filippo's, the apartment is very well renovated, we slept very well and there is everything you need. We were very well hosted. It feels like home. Still a little smell of humidity related to the period surely! The location is ideal for wandering around this beautiful area. Thanks!

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.

This penthouse in Siena completely stole our hearts! It was so spacious, peaceful, and beautifully designed—we truly didn’t want to leave. The views from the windows and terrace were absolutely breathtaking. I honestly think this is the best spot in all of Siena if you’re looking for stunning views of the city and countryside. The host was incredibly responsive and flexible, which made a huge difference for us. We were traveling with our two-year-old, and they went out of their way to accommodate his sleep schedule and make our check-in seamless. We’re so grateful for that extra care—it made our stay feel even more special. If you’re heading to Siena, don’t think twice—this place is pure magic.

Amazing apartment - stylish, astonishing views, great Aircon, loads of space. It’s situated on a beautiful square right slap bang in the middle of things - after spending 4 days here, we couldn’t wish for a better location. The building and square are very characterful yet quiet (except the amazing music floating up in the evenings). Great value - we had four nights for the cost of one night in a Florence 5-star, with loads more space. Things you might need to know: the huge windows have electric blinds, which either provide shade or blackout - nice! The two bathrooms are cute and functional but small. The kitchen also - well equipped but not much room to conjure up a gourmet meal. However the number of excellent restaurants within ten minutes walk is astonishing - just follow Edoardo’s recommendations.

We had the most amazing stay at Sibilla's apartment! It is STUNNINGLY decorated and almost makes it feel like you are staying in the Medici Chapel itself. The apartment had everything we needed, and the plant room/ sunroom was glorious to enjoy in the mornings/returning after a day's exploring. We met both Niccolo and Sibilia and both were so friendly and helpful. The area surrounding the apartment is perfect, with central Florence being a 20 minute walk away, and the restaurants/shops/wine bars of Santo Spirito being literally on your doorstep. This is the most enjoyable Air BnB we have ever stayed in, and would come back in a heartbeat! Grazie mille!!

It was beautiful and a great way to end our honeymoon. She connected us to a massage therapist. It was great.

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.

Thank you Andrea, Laura and team. We loved our stay at the Castello di Bossi. It’s very quiet and beautiful surroundings with a lovely clean apartment. Comfortable bed as well. Would recommend:)

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!!

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.

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!

Excellent location and beautiful apartment. Easy to get in self-check in and good communication with the host. Great kitchen, stocked with all the hardware you need. Common area was comfortable for the 4 of us. The view is amazing. Balconies on the water with close up views of Ponte Vecchio. Definitely one of the best places we've stayed in a 20 day trip in several cities.

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!