Pet-friendly holiday rentals in Gaiole in Chianti

This Airbnb was, without a doubt, the best my wife & I have ever stayed at. The house was spotless, cozy, & perfectly located with breathtaking views of Tuscany—but what truly made it unforgettable was Riccardo & his amazing family. From the moment we arrived, Riccardo went above & beyond to make us feel at home. When our rental car plans fell through, he stepped in without hesitation, becoming our personal driver. He took us grocery shopping, showed us around Chianti, & even drove us to Florence twice. Riccardo was always responsive, kind, & genuinely cared about our experience. We didn’t just find a beautiful place to stay—we found warmth, hospitality, & a real connection that made us feel like family. This stay was worth every dollar & more. A true home away from home. If we ever return to Tuscany, it will definitely be with Riccardo.

Great flat to explore Cortona! Excellent location and had everything you need

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.

Very good stay at Giulia's. Pleasant and spacious house. Good location to discover Chianti and its white paths.

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.

Catherine is a wonderful host, very friendly and helpful. We came in for business and the Airbnb was such a peaceful place to return to at the end of the day.

It's a really great place to stay with a great view. The bedding was clean and the bathroom was clean. There are two swings, a playground with a slide, a garden, and animals such as mountain rabbits, cats, mountain birds, snails... etc. that made the kids happy. I was grateful that the hosts were so kind and sweet. I recommend this accommodation that I want to go to again.

We really enjoyed our stay, except that it was too short! We will need to return for a longer stay to really allow the peace and calm there to sink in. Special thanks to Mario and his daughter for welcoming us even though we were delayed several hours by the power outage in France’s Alpes-Maritime region, where we were arriving from. The sitting area in the garden has a spectacular view of the surrounding Tuscan hills. Next time, we will make better use of it, including for star-gazing in the clear night sky.

Beautiful place, lovely views and areas to eat, drink and relax at the AirBnB. Great location, near to vineyards and local towns.

This was an incredible and relaxing getaway—we honestly wish we had stayed longer. The tower is just as magical as the photos, and the views, olive grove, and pool were even better than expected. The surrounding town is darling and quiet, with just a couple of small restaurants and markets, which made it feel like a true escape. Luca was kind and responsive throughout our stay. Just a few things to note: there are a lot of stairs, and you’ll want a smaller car to navigate the narrow roads leading up to the tower. It’s a real castle, so it’s older and rustic—but full of charm and clearly loved. The only downside was that the hot tub on the roof no longer works, which was a bit of a letdown. Still, we absolutely loved our time here and would highly recommend it.

Giuliani is a wonderful host who made us feel as if this slice of paradise was our home, too. The location, the meticulously restored home, the views all make for the ultimate Tuscan experience. But Giuliani and her husband bring it all together with their warmth and attentiveness. It was a tough place to say goodbye to — for now. If you are looking for a Tuscan experience, this is it. And remember to ask for the hosts’ home-cooked meal. It is a culinary experience in the very best sense.

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.

We thoroughly enjoyed the stay. Everything was very clean. What a great environment. We traveled with a 1-year-old child and were very warmly welcomed. For my daughter, there were many toys, a play mat, a cot and a high chair. The small playground was also impressive. Our highlight was the great sunset and of course the most beautiful pool we have experienced so far. We can only recommend it!

Our stay with Marta and her family could not have been nicer. We felt absolutely comfortable from the first moment. The property is absolutely spacious, lovingly furnished, incredibly well maintained and run with love. Marta and her family are absolutely lovely and take care of their guests very nicely. All wishes are fulfilled. The pizza evening was wonderful and a successful conclusion to our stay. If you are looking for a dreamy, secluded Tuscan ambience and loving hosts, "Poggio del Fattore" is the right place for you.

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!!!

Careful apartment, available host... everything is very nice! The gem, the hot tub. Highly recommended

One of the best places we've ever stayed and he explained why: Monia and her daughter Giusy have been very kind, good hosts and respond quickly. We loved the place: perfect for disconnecting and spending time surrounded by nature in a large, clean and comfortable house. In addition, the house was very well stocked, especially the kitchen: they left us many things for breakfast and also for dinner, which was enough for more than one day without having to go shopping at the supermarket! As parents, we also really appreciate that our baby's crib was made of wood, with a mattress and everything, just like at home. It wasn't a travel crib, so it turned out to be super comfortable for our baby. They also had a changing table and high chair, which were great for us. We'll definitely do it again in the future!

We had everything we needed for a very relaxing stay in rural Tuscany, away from the hustle and bustle of daily life. Our hosts, Alejandra and Filippo, were very welcoming, friendly and helpful with local recommendations.

The stay at Paola’s place was great. It was clean, easy to get to by car, and has a small parking lot right next to the door. Everything was as described and Paola responded quickly. Would recommend! You should bring earplugs and be prepared for a slow internet connection. The WiFi is slow and sometimes breaks apart completely, while mobile service isn’t much better. So this is great for a digital detox.

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!

Had a great stay in this place! Very friendly people, and a really clean facility! More than 5 stars!! Would stay there again for sure!

Beautiful home. Extremely clean. Riccardo was extremely responsive and made our check in process very easy. Definitely would stay again!

We - a family of seven adults - had a really great stay at Bernardino's house. The house itself was very cosy and charming and contained everything we needed. The pool and the pool area, to which only we had access, was a fantastic extra asset which we enjoyed a lot. The nearby surroundings were also very nice with vineyards and woods. We even spotted three seldom orchids and heard the pirol bird which is very exotic to us. At the same time, it was possible to walk to the nearby town of Gaiole in Chianti where many nice restaurants and cafes can be found.