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.

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!

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.

Can’t say enough about how great this house was! The views! The house is absolutely adorable! From a story book! Outdoor space was incredible! Loved making dinner in the kitchen (kinda made from local market which Sophia recommended which was amazing! I wish I could stay there for a week!!!

The main thing is Nada' s attention to every communication you sent, she responds the same day. Anything you asks for within reason, you get from Nada. It was a new experience for us in Tuscany but her property is combiniently located within 40 minutes to an hour and 30 from all the Tuscany turistic places.

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.

We had a brilliant week at Jakob and Margit’s house. Margit was so friendly and helpful (and gave us some wine and fresh eggs!). The views from the gardens are incredible and having the swimming pool was perfect. The local area has lots of great vineyards to visit and the house is close to Florence/Siena/Arezzo for day trips. It had everything we needed like a washing machine etc.

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.

We will definitely be back! The location is about 30-40 minutes from the main city in Florence. Federico recommended we rent a car but we didn’t want to drive in an area we were unfamiliar with. We were provided with the bus schedule which was very easy to take to the city. We planned ahead and bought some groceries in Florence before heading back to the property. We got lucky with getting taxis at the property to eat at a nearby restaurant (Ristorante San Martino) but it wasn’t as convenient as getting one in Florence (had to wait a bit). The place was just as described, very relaxing and just what we wanted! All in all a great experience. We were so sad to leave!

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.

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

We’ve stayed in many many airbnbs, and this is the most interesting and beautiful one we’ve stayed at by far. It’s an authentic Tuscan villa built around 1700 and loved by the current owners / hosts. You can tell how much love and care they put into maintaining this place - in particular the garden and olive farm! Marta was an incredible host, greeting us when we arrived, showing us around and even gifting us some olive oil from their farm when we didn’t have cash! We absolutely loved staying here and plan on coming back with friends! Cannot recommend enough!!

5 Stars – A Tuscan Dream Come True! Our stay at Francesco’s private resort-style retreat in the hills of Tuscany was absolutely magical. The location is stunning—peaceful, picturesque, and the perfect escape into the beauty of the Italian countryside. The rustic room had so much charm and comfort, and the property itself was amazing, with not one but two beautiful pools to relax by. One of the highlights was the on-site restaurant. The free breakfast was far beyond the typical offering—not just muffins, but a full, authentic Italian breakfast that we looked forward to each morning. Dinner was just as impressive, showcasing delicious local flavors and warm hospitality. It was also a great jumping-off point for exploring the region—we took a lovely day trip to Siena with ease. This place is a hidden gem, and we’d return in a heartbeat. Highly recommended for anyone looking to experience the best of Tuscany!

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!

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.

We had a great time staying at Sara's, the hosts are very friendly and kind. The house and the neighborhood are beautiful and quiet, we were able to relax. The apartment had everything we needed. Sara's father also gave us a tour to their museum, we absolutely loved it and great conversation together. Highly recommend!

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!

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

What a great winery! The location is really unique, the accommodation is in the middle of the vineyard and very quiet. Alessandro our host was very nice, gave us a warm welcome and took a lot of time to show us everything (including the wines). We were also very happy with the accommodation, which was beautifully furnished and had everything we needed.