Apartment holiday rentals in Radda in Chianti

You will be literally in History, that is, in a 13th-century castle: there are some drawbacks (such as the access staircase, rather steep), 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 an authentic 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 10 minutes by car from the center of Radda in Chianti. Alessandro (assisted by Loriana) was an exemplary host in all respects.

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

Sweet apartment right on the piazza in Greve. We loved the balcony and the comfy bed. The entire apartment is nicely decorated and perfectly located for feeling part of the welcoming town of Greve. Thank you to Mascia for carefully tending to every detail!

If Lorenzo's place is available, just book it. You couldn't be more centrally located. Everything in Florence is walking distance from the unit. The view of the Duomo from the main room is stunning. The stairs can be a little tough if you have heavy luggage but the elevator helps a lot. The air conditioning in the unit is also top notch. It was very hot during our stay and walking back in to the cold unit felt great. Thanks for an awesome stay!

An ideal place to tour Tuscany in a relaxed way and then relax in an apartment with a nice garden.

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.

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!

Excellent stay in this beautiful haven of beauty and silence. Staff hyper .merci a landreana more particularly . The team is super responsive, everything is perfect

Marvelous place, Sara is very friendly and helpful host. Can’t wait to visit this place again.

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!

We had a lovely stay! Elisa and Alessandro are so kind and very helpful with anything we needed. They made a reservation at a restaurant for us when everything was fully booked. Thank you for your great hospitality!

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:)

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

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!!

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

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!

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.

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.

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.