Family-friendly holiday rentals in Castellina in Chianti

Incredible trip. Paola and Michele were so friendly and welcoming. Always there to give advice and make sure you had everything you needed. The little converted hay barn was just beautiful and lovely. Location wise it just couldn’t be beaten. The garden was amazing and we ate outside morning and night, easy access to amazing Tuscany countryside and also a short trip on the train to Florence from Montevarchi. Loved every minute we were there and we were sorry to leave. Would highly recommend.

If I could move in here permanently, I would. What a gorgeous stay with responsive and respectful hosts. Everything was as described, the hot tub was glorious, and we loved looking through the binder of photos of painstaking restoration over the years.

I can not say enough about Alessandra and her amazing land! It was the most magical place we have ever been to. We are taking a 3 month trip, hitting up 21 cities in Europe and this is BY far the best! She was so kind and took us shopping and back to our train! She was always there when we needed her.thank you Alessandra we will see you next year!

Authentic Tuscan countryside experience, with amazing views and excellent facilities. Well located if you want to explore all that Tuscany has to offer.

We had a wonderful week in Gloria's house. Our four-legged friend also felt totally comfortable in nature. The house is small but nice and has everything you need. The property is a nice size and is perfect for eating outside, relaxing in the hot tub or just lying in the sun. The way to the house is a little challenging, but with a normal car and a little driving experience it can be mastered. Gloria was always available to us and gave us good excursion tips for the area in advance. Even with any inquiries, she always reacted very quickly and helped us. It is perfect for simply getting out and enjoying the nature and tranquility of Tuscany. We will be happy to come back!

We just checked out of this wonderful villa today, and it has truly been one of the most special places we’ve ever stayed. We arrived with my husband’s parents, my husband, and our toddler, and from the moment we got there, everything exceeded our expectations. Alex greeted us warmly, gave us a tour of the villa and the property, and provided detailed printed information about nearby restaurants, supermarkets, cafés, bakeries, and wine tours. The property also produces its own wine, which was available for purchase and could be conveniently delivered to our villa during our stay. Alex shared his contact number and made himself available in case we needed anything—which we really appreciated. One of the highlights of the property was the stunning infinity pool overlooking the vineyard and offering breathtaking views. It was the perfect setting to disconnect and truly live in the moment. The air conditioning and hot water worked perfectly. Thank you Alex!

We had a really good time at this place. It was spacious, clean, and worked perfectly for our group. There were plenty of bathrooms, and the house had all the amenities you might need for a comfortable stay. The outdoor space was a big plus—especially the terrace and patio area with the big table, which was great for hanging out and having meals together. The location is honestly perfect—super peaceful, but just a short drive to Florence, great local restaurants, and vineyards. Also, there was tons of parking space, which made things super easy for us. Check-in was smooth and the host was really helpful. Would definitely stay here again.

We can absolutely recommend it! Everything is as described in the text and as shown in the photos. Located about 2 km outside the totally cute village of Casole de Elsa. Andrea + Barbara provided all the necessary information for the journey and many great tips on site, always with the corresponding links. For example, our arrival was delayed to about 10:15 pm due to traffic. Was no problem, we were in contact and when we arrived, Andrea personally received us. And if we had a question during our stay, an answer always came very quickly. (Where is the best place to park in Siena, how do you best get to Florence, ...)

The pictures don’t do the beauty of the space justice. Maria, the housekeeper who lives in the basement unit was very discrete. Dawn was our host and set us up some incredible reservations, as well as helped us with a transportation issue. The view is otherworldly off the back porch, which overlooks olive trees. There are many adorable tortoises that live in the backyard and are very fun to watch. Close drive from the tram as well as many incredible restaurants. Take the cooking class with Maria!!! It was a trip highlight. If you stay here, you will definitely want a car.

Our stay at Sonia’s place was like a week in a fairy tale. To stay in an 18th century home in Tuscany with the front door on the town square and the private rear terrace with a million dollar view was extraordinary. As for comforts & conveniences: There’s a parking space in the gated backyard, the beds are very comfortable, and the kitchen has lots of wine glasses. There’s also a well-stocked supermarket at the bottom of the backyard stairs. And if you see the food truck just below the center of town, be sure to stop for a sandwich. If you can get away from the terrace, Carolyn & Sonia recommended the restaurant Enoteca Baldi, and we do too.

Wow-10 days spent at Alec's villa and could have stayed longer! The age and beauty of this place makes you feel transported back in time. From the stone walls, the detailed wall paintings, furniture and decor, to the solid doors easily hundreds of years old... We spent hours just speaking of it's history. The house is clean, spacious, and had plenty of room for our family of 8. It is situated on a small family vineyard at the top of an incredibly windey road. There outdoor space was safe/secluded for my kids. The hill made for wonderful beautiful views and sunrise. However, as with much of Tuscany, we were glad our rental cars weren't too big! The closest town is 5 minutes away and has a few restaurants... Though not somewhere you can have coffee or walk the streets. About 15 minutes away is San Casciano where you can find coffee shops, restaurants, stores etc. Alec is a perfect host... helpful, responsive, and answered dozens of questions weekly. Book dinner at A Casa Mia for sure!

Le Bartaline is a wonderful place to stay. I stayed in the Porchereccia, it had everything I needed, such a lovely apartment. The surroundings are beautiful, I liked to walk out a bit onto the road to enjoy the afternoon light overlooking the wine yards and hills. The gift of a bottle of delicious wine and bottle of olive oil is a much appreciated welcome! There is an amazing winebar with delicious food walking distance (you’ll need to walk up the hill) called Enoteca Baldi, highly recommended.

Staying at Agrigreen La Lama was hands down the best Airbnb experience I’ve ever had. From the moment we arrived, Rita welcomed us with such warmth and hospitality that we felt at home. The property is peaceful, beautifully maintained, and full of charm—surrounded by nature and the kind of quiet that soothes the soul. One of the most memorable parts of our stay was getting to cook in Rita’s own home, which she generously opened to us. It was such a unique and personal experience that made us feel truly connected to the space and the spirit of the farm. If you’re looking for a place to slow down, feel grounded, and enjoy genuine hospitality, Rita’s space is an absolute gem. I’m already looking forward to the day I can return.

The apartment was exactly as advertised. In fact, not sure the pictures do it justice. It is a beautiful setting - peaceful and relaxing. The space in the apartment was very usable with two bathrooms and a nice kitchen. Martina was super helpful and communicated well with fast response time. Great recommendations for walks and restaurants. I can’t say enough nice things about her. Just an ideal host.

My wife, brother-in-law, and I had an incredible time in Montepulciano, and Giacomo’s apartment was the perfect place from where we started out daily adventures, took afternoon naps, and then headed out for fantastic dinners. Giacomo’s apartment was excellent, making it easy to get settled after a long day of travel. Giacomo guided us into the temporary parking spot when we got lost for a few minutes, and was quick to assist with any questions we had during our stay. The restaurant recommendations were all excellent, as well as the other activities he suggested. We will definitely stay here again when we visit Montepulciano!

Perfect location - could not select a more beautiful setting. Il Paluffo manages to feel luxurious and green as well as rustic with modern comforts all at the same time. The location is stunning - pictures do not do it justice. Il Paluffo is tastefully decorated, intimate with lots of amenities, and unique offerings. There was a cooking class offered while we were there! This is a truly unique and magical place, the perfect Tuscany experience.

We can't imagine a more beautiful place to stay while we visited Chianti! The location is absolutely heavenly, and Emanuela's home is stunning. Everything was so comfortable, and our family particularly loved spending time outside and enjoying the pool. It's conveniently located for several Tuscan day trips, and there are many amazing wineries nearby. And the icing on the cake were Emanuela and Giovanni, who went above and beyond in helping us throughout our trip - from recommendations and help with reservations to having a few food items and coffee stocked for our first day's breakfast. Easily the best hosts we've ever enjoyed in our years staying in Airbnbs!

Great location and friendly hosts!

Overall, the stay was very good. The property is beautiful, located in an excellent, private, and quiet area — yet just a 5-minute drive from the town center. The apartment was tidy and clean, although it felt a bit unventilated and slightly dusty. One important point to note is that during checkout, guests are required to dispose of the trash themselves using a designated city bin system, which involves a special card that must be returned to the host. This can be a bit of a hassle, especially for guests staying only a few days. All in all, a good and recommended experience.

Very friendly and helpful host, Massimo made us feel at home. A beautiful apartment overlooking some incredible views. Lovely clean pool. Just a perfect holiday all round!

This place is truly beautiful. Be aware of the location, as the address is easier to find if you look for “Agriturismo Il Casalino” in Monteriggioni. The property is beautifully taken care of. The garden has different levels with the highlight being a relatively large pool. You’ll find olive trees and all other kind of herbs and plants across the property. It is really a beautiful green oasis. The barbecue we used twice in 5 days, great addition. The pool is worth to be mentioned. The pool is quite large for a private pool and quite deep, don’t be fooled. This also makes to pool stay fresh all day. Otherwise I would not recommend to stay at this place without a car. It is not very well connected and even walks are difficult from the property. The only „weakness” would be the poor connection in the house. Outside, by the pool the connection is fine but in the house it doesn’t really work. Finally, I can only recommend staying here for some quiet days.

I had a happy time in a house that looked like it was in a movie in a beautiful natural environment. I think I'll keep my time in Kian Tti as a good memory thanks to the kind and friendly host who responds so quickly. It was a little difficult at first for the city girls who were new to the road to the accommodation, but it wasn't difficult when they got used to it. It's perfect for watching the sunrise and sunset. I left today, but I want to go again.

Odina was the perfect spot to relax. Beautiful and comfortable accommodation, wonderful dinners and great communication. Would definitely recommend Odina to people wanting to get away from the city and relax in the countryside.

This place is something else! The views, the pool, the houses, the interior - it’s something else. We stayed with our 18 month old and had such a happy time - surrounded by nature in such gorgeous accommodation and a kiddy kitchen / toys which were perfect for Otis. It’s simply beautiful and Martina is so helpful - highly recommend with a family or groups of friends for a zen and unique time. Close to lots of gorgeous places and Martina has wonderful recommendations. Only watch out is the 2km dirt track road to get to the location but it’s 100% worth it and quite fun! Enjoy - we can’t wait to come back :)