Apartment holiday rentals in Castellina 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 facility 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. From here, we were able to visit some cities such as Florence and Siena, and here, too, Ana had great tips for suitable restaurants. We will be happy to come back!

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!!

Fantastic couple of days in Panzano! The views are spectacular, such a beautiful place. Veronica is the perfect host, so responsive, nothing was too much. I wish we had stayed longer....... thankfully, there is always next time 😁

We have been visiting Tuscany for about 30 years. This locality is certainly the best we have ever lived in. Martina and her parents are very loving and warm to their guests. We can only recommend this offer and we will certainly come back. Best regards and thanks for the wonderful stay Allfred and Sieglinde

We had a very nice stay in the Chianti region. The cottage was very comfortable, spacious and clean, and the terrace was super with a beautiful view. The cottage is located on a plot with a number of other holiday apartments. The grounds are beautifully maintained, located between the olive trees and also the swimming pool and tennis court were great. Marco and his parents welcomed us well and always responded quickly. You can also take delicious wine and olive oil to the Netherlands, made by the owner himself! Can only recommend.

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.

We have now been to Elisa and Alessandro's accommodation for the second time – and it was simply beautiful and absolutely relaxing again! The place is a real oasis where you can switch off perfectly. Elisa and Alessandro are extremely helpful and warm. They provided us with great tips for activities and restaurants, so we could enjoy our stay all around. We'd love to come back and highly recommend this place!

We had a wonderful 4 day stay, thank you for your hospitality, to all the staff and family. First class, recommended restaurants plus made reservations for us, which were needed, and recommended sites to visit. Rooms were spacious and clean, grounds were beautiful, wine tasting and Stephan’s knowledge of wine making made the tour. We also had breakfast every morning, and one evening had a dinner, recommended. A beautiful couple, so glad we meet them. Hopefully we will be back again.

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 !

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.

Clara was responsive and helpful. She was there to meet us and help us with parking and walked us through the entire house. She was wonderful. The space was perfect with a wonderful patio. Totally would recommend.

We had such a great time in Florence and this apartment was the perfect home base! The mix of brick walls and modern furniture gave it a cozy vibe, and the mezzanine was a fun bonus for our daughters. The layout was super comfy and well-designed, and we felt like we had a quiet spot close to so many restaurants and historic areas. Big thanks to our host Beppe—he was super friendly, easy to talk to, and made everything so smooth. One of the best hosts we have had in terms of communication and helpfulness at all times. I also strongly recommend checking out his restaurant Samambaia Caffe & Cucina! Definitely recommend staying here and hope to be back!

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 setting, 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 – genuine kindness, as if you were staying with family. You will immediately feel welcome and at ease 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 place to stay, it is an experience that will stay with you. For those who really want to experience Tuscany

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!

Our stay at Luca’s place in Florence was wonderful. The location was extremely convenient with main attractions like the uffizi and galleria dell’academia just a short walk away. The apartment is also located in a very nice square that is lively and fun, but not noisy from the room. There are many restaurants and shops just down the stairs. The room itself was all that we could have wanted. The whirlpool tub was a very nice feature, the bed was conformable, and the atmosphere of the room was very cozy. If we return to Florence, we would love to stay at Luca’s place again!

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.

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.

Emily's apartment is the perfect location to explore Lucca. She was extremely helpful when communicating and very prompt when replying to any queries.

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.

We loved our stay here. Right next to the Duomo and close to everything in Florence making it super easy to get around. Loved the inside of the apartment too and was overall amazing. Silvia was very helpful and great!