Pet-friendly vacation 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.

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 for discovering Chianti and its white roads.

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!!!

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.

This accommodation has a really nice view. The bedding was clean and the bathroom was clean. There are two swings, a playground with a slide, a garden, and the kids were happy with animals such as mountain rabbits, cats, mountain birds, snails... etc. 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.

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.

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 will 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.

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 equipped, incredibly well maintained and run with love. Marta and her family are absolutely lovely and take care of their guests very nicely. All your wishes are fulfilled. The pizza evening was wonderful and a successful end to our stay. If you are looking for a fantastic, secluded Tuscan ambience and loving hosts, "Poggio del Fattore" is the place to be.

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.

Had a great time! The beautifully maintained garden, the pool, the house: everything was exactly as we had wished. A big thank you to Lorenzo for his great advice and warm support. Thank you for everything! We had a blast! The beautifully maintained garden, the pool, the house: everything was just as you wanted it. A big thank you to Lorenzo for the excellent advice and his cordial support. Grazie di tutto!

Well-kept apartment, available host... everything very nice! The gem, the hot tub. Highly recommended

One of the best places we've stayed and he explained why: Monia and her daughter Giusy were very kind, good hosts and respond quickly. We loved the place: perfect to disconnect and spend 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! Also as parents we really appreciate that the crib for our baby was wooden, with its mattress and everything, 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. In a future opportunity, we will surely repeat!

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!

Because of the gorgeous remoteness, it took us some time to locate the entrance gate, but then we entered heaven. The place is captivating in so many ways - the historic stone structure, the entrancing views, the homey & artistic decor. It was like visiting a friend and being welcomed into a warm family retreat. Prepare to cocoon as there is no nearby store and few restaurant options. The roads were in poor condition due to recent severe storms, so it was an adventure to make our way in the evening to Castellina for dinner and back . The road in the opposite direction toward Radda was completely closed! But I loved our short stay and will dream of returning.