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

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.

Hands down our favorite part of our two weeks in Italy! Casa Al Poggio was our Tuscan home away from home. We went and did all the things… Florence, Cinque Terre, San Gimignano, Montepulciano, etc. But coming “home” to this place was the best. So peaceful and picturesque looking across the valley at the Badia Di Passignano. We cooked many meals in the well stocked kitchen and my husband loved the rustic BBQ. Fresh herbs in the garden and the smell of jasmine blooming on the patio. Book yourself extra time here…you won’t want to leave! Emanuele & Tamara are the kindest people. Take them up on all of their restaurant recommendations. Everyone one was a hit! We can’t wait to go back.

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

We had the best week in Nada’s home with our friends who travelled from Australia. The villa was so cute and cosy and had everything you would need. Nada is a great host who was very responsive and extremely friendly, it was just a shame we didn’t get to meet her in person. The main highlight for us was when Viola (Nada’s daughter) came to the villa and did a cooking class with us. It was fantastic and one not to be missed! We made bruschetta, homemade pasta and sauce and a lemon tiramisu. We made pasta and bruschetta literally every night after as it was just so good. From the villa we travelled around in our hire cars and saw the delightful towns/villages such as San Giginano, Certaldo, Siena, Greve in Chianti, climbed up the hill to Montefioralle, Radda in Chianti, Volpaia and the local village of Barberino Val D’Elsa. I highly recommend you visit each as all close enough for a day out it combine a couple in a day. You will not be disappointed at Casa Di Nada. We loved it 😊

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.

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

Excellent stay in this beautiful haven of beauty and silence. Staff hyper .merci a landreana more particularly . The team is super responsive, everything is perfect

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.

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.

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.

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.

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 ❤️

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.

Elena's Airbnb is great! The location is perfect for trips around the Tuscan countryside, and you'll be surrounded by peace and quiet. Even though it’s a small town, there are good restaurant options and a supermarket very close by. The accommodation is small but very comfortable (ideal for 2 people, but we managed just fine with 4). It has everything needed for a great stay, including excellent internet. Parking is outside the property in an open area, but we always found a spot during the week we spent in Cavriglia. Elena is very easy to communicate with, gave clear instructions, and is a very kind person! The bottle of wine she left for us was the cherry on top! We recommend it with our eyes closed.

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.

Quiet and pleasant condo in a good location.

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.