Pet-friendly holiday rentals in Castellina in Chianti

My husband and I, plus our French Bulldog, had the pleasure of staying here for just over 3 weeks. Immediately felt like home, and host family had everything to do with that! Highly recommend. stunning views, fabulous location and some of the most gracious people I've ever met.

We loved our stay in this beautiful vacation home, perfectly located in the peaceful Tuscan countryside. Sandra is a very attentive host, she was always available for any questions and proactively communicated making the check in process very easy. The house is well appointed. I would like to point out though that only one of the bedrooms has total privacy as the other two bedrooms can only be closed off by a curtain. This contributed to its charm as a lot of the old features of the house were preserved, and wasn't a problem for us. We definitely would come back. Thank you Sandra.

We loved our airbnb! Antonella is a top host! She gave us nice tips and was very accessible. The location was very good, we visited many nice cities/towns and Colle di Val d'Elsa is beautiful and has very friendly local residents 🤩😍

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 :)

This house is so beautiful. It is at the bottom of town.. if you drive it’s perfect because you can park near the house, cute coffee shop and free parking if you get lucky! View is so beautiful both from the house and walking into town. I’m really happy with location and house. He was very helpful and responsive. Would stay again!

We loved our stay in Pietro’s beautiful, unique and historical place. The house is charming, well-equipped and spacious, the scenery and view are stunning, and the peace of the mountains is soothing. The drive up the mountains is an experience too! Communication with Pietro was easy, fast and kind.

Don’t hesitate to book this beautiful Airbnb which was thoughtfully restored to reflect the history of the area. You won’t want to leave. We explored Certaldo Alto and Montefioralle- both amazing sites. The pool area was perfection and we couldn’t get enough of the landscape! Couldn’t stayed a week!!!

Very lovely secluded country villa..

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

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.

Christine and John were the best hosts, making this incredible location even more enjoyable. They went above and beyond, recommending restaurants, wineries and experiences that made our trip unforgettable. Christine also helped us get our lost luggage back, ringing the airport for us and liaising with a driver in Florence to pick it up and drop it off to us. Incredible service. Absolutely recommend!

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!

This was such an amazing stay! Very quiet, peaceful, and relaxing stay far away from the major cities. Beautiful views from everywhere! Would recommend doing their wine tour on site. It was fun, informative, and delicious! You definitely will need a car to get to this place in addition to restaurants and grocery stores. Would highly recommend this place!

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.

This has been the standout accommodation of our Italian tour so far. The photos do not show how amazing this place is. It’s on a vineyard and olive farm with the option for breakfasts (which were fabulous) and we also had a shred meal with others at the accommodation on one night. The food was wonderful and the atmosphere set to be relaxed with several courses taken over a few hours and flowing local wines. The apartment was beautiful and spacious with a very comfortable bed room. We ate in on a few nights and the kitchen was well equipped for making food. Anna was exceptional as a host always very helpful and with such a cheerful positivity. We chose to be away from the main towns to have a peaceful recharge and this accommodation gave us exactly that. Take a walk through the vineyards and capture a sunset that will be etched into your memories. Thanks again Anna for a wonderful stay ❤️

Wow- a beautiful location, villa and host. Magical stay as our last part of holiday in Italy. Absolutely recommend. 3km to Poggibonsi for groceries/wine refills. Proximity to other Tuscan towns to visit is super close and easy driving.

We had a beautiful stay at Alessandro’s property. The property is in the middle of the Tuscan hills with gorgeous views on all sides and feels very undisturbed and untouched. We were super lucky to have the place to ourselves the whole time and felt totally at peace. The apartment was beautiful and incredibly spacious with everything we needed, with lots of space in the grounds to go for walks and sit outside and enjoy the views and weather. Panzano is only a 7 minute drive away for supermarkets (small Co-op and village shop etc) and restaurants, and Alessandro was very responsive when we had any questions or if we needed anything. We couldn’t have been happier and will definitely be back next year!

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.

The place was beautiful and so peaceful. Bianca is a great host. She was very friendly and communicated well and gave us a lot of recommendations. 5 ⭐️

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!

Spectacular view. Relaxing after a long trip thru wineries. Town was very cute and comfortable

The best place in whole tuscany! We had whole garden for ourself, a lot of fresh spices in a garden which we could use. Peace and homely atmosphere as vacation at your's grandma place! 11/10 I reccomend olive oil host produces!

Paola’s place was an incredible getaway for the two of us - we played fetch with Nilde in the garden, had a night where Paola taught us to make pasta and tiramisu, and enjoyed the best sunsets. If you get a chance, definitely check out Osteria Alla Villa for dinner. We will definitely be back! Thank you Paola for the hospitality and making our first trip to Tuscany so special.