Villa vacation rentals in Castellina in Chianti

The stay was wonderful! The villa was amazing, the views, the furniture, the rooms and the pool. We were so happy to be there. The rooms were new and clean. Every detail was taken care of. Christina was incredibly helpful and always available. Without her, we'd be lost. Unfortunately, we often had private problems and every time she helped us and brought us solutions. For me and my friends, this stay was unforgettable!

This little hamlet was ideal for a group of several families wanting a Tuscan holiday. Christina was a very responsive host, always available for help and suggestions. One down side was the distance from many of the Tuscan attractions such as Florence and Sienna. The hamlet is reasonably remote so is ideal for those who want a secluded holiday rather than those who want to see the sights of Tuscany.

Five friends made to feel very welcome to this beautiful spacious villa with a lovely pool set amongst olive groves. The scenery that surrounded us was beautiful. Invited to Mark's villa who shared his knowledge and history of the olive groves which was very interesting and the hospitality received was first class (vino and yummy bruschetta's). This was the perfect place to stay and would highly recommend.

The house was amazing, perfect fit for our group of 10 people. The main house as well as the additional apartment were very clean, well equipped with everything you need and the highlight was the pool and jacuzzi. Great place to calm down and have private space with some friends or a big family. The check-in was easy and the lady was very friendly, had some suggestions for our stay and is professional. The property was clean, cute tuscany decorations of the rooms and all in all it felt like home.

Fantastic all around experience. Thank you Elio and team 🙏🙏

Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!

Our stay at Terra Antica was a dream. The location is perfect and the property and villa are exceptional. We were close enough to town to get to restaurants and shopping and then come back for some quiet relaxing time. There are numerous wineries to visit in the area. Day trips to other local towns are easy to do as well. The private jacuzzi was an extra bonus & we used it several times during our stay. We will be back again!

Stunning villa in a beautiful setting. Francesco gave excellent directions & the peace & tranquility out in the Tuscan countryside was wonderful. Francesco was exceptionally responsive & gave great local advice. We loved the little towns nearby and can’t wait to return soon. Highly recommended. Jack.

We chose Il Sole del Sodo because it had 6 en-suite rooms, a pool, was close to a town and a train station and had a well- regarded host who could provide extras like breakfast, dinners, cooking classes and olive oil tastings e.g. Claudia! While rustic, the villa’s charm and peaceful spaces draw you right in and Claudia’s hospitality is unsurpassed. The villa fronts to the road to Cortona and backs to a field of sunflowers. Our family and friends dined on the private patio and found a back way to walk up to Cortona for exercise. A unique and wonderful experience!

Our stay at this beautiful Tuscany villa was truly unforgettable. The home perfectly blends charming, traditional Tuscan character with all the modern amenities we could possibly need. From the moment we arrived, we were enchanted by the authentic details — rustic beams, stone walls, and stunning countryside views — all while enjoying updated comforts like a fully equipped kitchen, high-speed internet, and luxurious bathrooms. It was the perfect balance of old-world charm and contemporary convenience. We couldn’t have asked for a better place to experience the magic of Tuscany. Highly recommend!

We (7 girlfriends) enjoyed the stay in the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She has sent us a lot of tips about the area (also the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed anything, there was a very quick response. The villa is well equipped and the surroundings beautiful. Parking has enough. Only the potholes and the access to the villa are a bit challenging - but doable!

We absolutely enjoyed our stay. It felt like home from day one. The views are phenomenal; the garden is peaceful and fragrant. The kitchen is a delight to cook in. We walked into the beautiful village of Panzano multiple times (some hills which helped us burn off the pasta calories!). We didn’t want to leave.

Thank you!! We enjoyed our vacation with 9 friends! A little humid because of the weather, but the place is ideal in summer and comforting by the fire when the good weather is not present!

The house is amazing and the exterior is beautiful

We had an excellent time staying at this family home with an amazing view of Torrita di Siena. Great access to many popular hill towns (Cortona, Montepulciano, Pienza, Montalcino, etc). The house and property are beautiful, very private and populated with song birds and olive trees. The hosts are charming and very welcoming. They provided us with all the recommendations we needed and were readily available whenever we wanted to communicate with them. The house is well appointed and has multiple ways to cook from gas range to pizza oven and wood fired grill. I really liked using the giant pinecones as fire starter. We would definitely return and hope to. Such a precious slice of paradise.

We had a marvelous stay at Villa Sestuccia. The house is spacious, as are the grounds. Both are well maintained. There is ample room with different areas to relax indoors and outside. We communicated with Briggita who was quick to respond, always friendly and always helpful. We particularly liked the location which has easy access to many spots of interest and restaurants. We enjoyed collecting eggs in the morning for our breakfast - such a fun touch. We highly recommend Villa Sestuccia and would not hesitate to stay here again.

We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!

We loved our stay at this beautiful place! It was extremely peaceful and our family had a great time!

The stay was beautiful. The view is fantastic, the pool very clean, surrounded by a beautiful, huge garden. Breakfast on the terrace is fantastic as the kitchen goes right to the terrace. The house is beautifully decorated and very clean. the air conditioning works perfectly, the nearest supermarket can be reached by car in less than 15 minutes, as well as there are various restaurants that can be reached in less than 20 minutes by car. Like that of The Sor Paolo or the Barrachina.

Francesco is nice:) He brought us welcome pizzas and dessert. His response is instant. The place is quiet which provide you completely private place. Just a bit far from town if you cannot drive yourselves. If you have cars, it is not a problem, just few minutes drive from town. The place looks exactly the same as the pictures, clean and tidy. Definitely enough space for 8 adults. Recommend.

We had a wonderful stay at the villa in Tuscany and felt at home right away. The hosts, Silvana, Iacoppo, and Bruno, took excellent care of us and were always attentive to our needs. The villa itself is spacious and well-equipped with everything one could ask for. The beautiful pool with its stunning views and the cozy fireplace area were definite highlights. It was the perfect place to unwind and enjoy the Tuscan countryside. Thank you again for an unforgettable stay!

Beautiful house in the vines surrounded by sumptuous hillsides in an incredible postcard setting. Perfect for gatherings for families or with friends. The location is ideal to radiate between Siena, Florence and Chianti or resting while enjoying the pool. Elisa, always attentive, is very responsive and will respond almost without delay.

We were welcomed by the host herself in this wonderful charming and peaceful villa. Perfectly maintained and great pool for the kids. Beautiful garden with lots of fresh herbs to cook with.

Absolutely wonderful space for our five days in Tuscany with four adults and two toddlers. It was too cold for the pool to be open but we used the heated tub a couple days. Heads up about the tub- it took 1-2 days to fully heat up bc it is heated by building a fire. Then once it heated up it was wayyy too hot, so then it took a day to fully cool down to be safe for humans. It was a fun adventure to figure out!! There was so much space for the kiddos to explore and play in. The view is breathtaking. You are far enough from the towns to feel like you can completely relax but also close enough to do day trips to nearby towns. Heavenly week! There’s a cute farmers market on Friday mornings in paciano where there’s a cheese stand that had the most incredible cheeses! Leslie the point of contact person was super responsive and welcoming. The wind slammed the door shut one morning which locked us out but Leslie acted quickly and was able to get us back in remarkably fast! Best week ever!