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.

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.

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.

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.

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. Perfect for watching the sunrise and sunset. I left today, but I want to go again.

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!

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 your wishes are fulfilled. The pizza evening was wonderful and a successful end 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.

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 here's 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 the cot for our baby was made of wood, with its mattress and everything, just like at home. It wasn't a travel cot, 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 repeat it 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.

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!

Home is beautiful! Very quiet and peaceful. Exactly what we were looking for after coming from tourist filled Venice! She even had cold water for us in the fridge and breakfast foods available to eat.