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 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!

We enjoyed staying in Laura's place.

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.

Our stay at Le Cinciole was our Tuscan country stay dream come true! After a few days in Rome I’m so glad we rented a car and made the drive to Tuscany to relax and unwind! Valerie and Luca are warm welcoming hosts that make you feel at home in their beautiful authentic country style guesthouse situated in their organic vineyards. The only sounds you hear are birds singing (even a Cuckoo bird) and the stars at night are brilliant in the county sky. We had an amazing wine tasting and an informative interesting tour of the winery operation. Valerie arranged for a local chef to prepare a private 3 course Tuscan dinner for us at the property! Our accommodation was on 2 levels - a bedroom and bath on each, which was nice for us as my husband and I were travelling with our adult daughter. The little historical village of Panzano is a 15 minute walk. I would love to return here again someday! Thank you Valerie You are wonderful !

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!

MEA Casa is one of those rare places that instantly feels like home. Elena and Martin are the most relaxed and welcoming hosts we’ve ever met genuinely fun to share a glass of wine with. The views are stunning, surrounded by vineyards and olive groves, and there’s even a natural spring on the property where you can fill your bottle with fresh mountain water. A hidden waterfall just 15 minutes away was the perfect surprise for a refreshing swim. The pool area is clean, peaceful, and beautifully designed, with hammocks, loungers, and cozy sofas. We were lucky to join a spontaneous wine tasting hosted by a neighboring estate—one of many special touches. Our room was spacious, stylish, and well-equipped. There’s also a product room with their own olive oil, wines, and local treats. Everything is done with love and care. It’s no wonder people return every year—we’re sure we’ll be back too. Highly recommended for a warm and unforgettable Tuscan stay.

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.

Communication with Gael was extremely easy. Although he was out of town, co-hosts Angelo and Alessandro were super cordial and attentive. We really felt at home. We would definitely come back a million times!!!

We had a wonderful few days here while touring Italy. The pool is fantastic as well as the additional facilities such as boules and table tennis. There is plenty of outdoor seating to enjoy the sunset on an evening. We would love to come back here again and would highly recommend.

Excellent stay in this haven of beauty and magnificent silence. Hyper staff. Thanks to Landreana in particular. The team is super responsive, everything is perfect.

Amazingly friendly hosts! So far this was our favorite experience on our vacation! We did the wine tasting followed by cooking class while staying here, I can’t recommend it enough! The air bnb was like nothing I’ve ever seen before, so unique and cute!

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!

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.

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.

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

Easy check in and out. Beautiful space and much bigger than expected. Great place to relax and explore if staying in the city. Really no negatives, book it and be happy.

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!

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!

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.

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!