Apartment holiday rentals in Gaiole in Chianti

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!

Excellent stay in this haven of beauty and magnificent silence. Hyper staff. Thanks to Landreana in particular. The team is super responsive, everything is perfect

Beautiful property and a spotless, stylish room. The host was incredibly kind and attentive—made us feel right at home. Would definitely stay again!

Marvelous place, Sara is very friendly and helpful host. Can’t wait to visit this place again.

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.

AMAZING stay. More beautiful than the photos. Spotless. 5 min drive to Siena. View of the wine country. Bed was more comfortable than my bed at home. Owner was extremely friendly and helpful.

Highly recommend anyone new to Italy to try San gimigano first. Staying here allowed us flexibility to explore other cities and had plenty of great spots in walking distance. Lorenzo provided fantastic recommendations and assisted with everything we asked for.

Great place, clean and in a great location close to everything. The only thing is the bed is quite hard, but everything else was perfect.

Amazingly friendly hosts! So far this was our favorite experience on our vacation! We did the wine tasting followed by cooking class while staying here, I can’t recommend it enough! The air bnb was like nothing I’ve ever seen before, so unique and cute!

We had a wonderful 4 day stay, thank you for your hospitality, to all the staff and family. First class, recommended restaurants plus made reservations for us, which were needed, and recommended sites to visit. Rooms were spacious and clean, grounds were beautiful, wine tasting and Stephan’s knowledge of wine making made the tour. We also had breakfast every morning, and one evening had a dinner, recommended. A beautiful couple, so glad we meet them. Hopefully we will be back again.

We stayed in the 3 bedroom unit. It was spacious with breathtaking views. A large patio to sit on that overlooked rolling hillside. Our host was great with providing recommendations and responded quickly. For my husband and I we would not choose this location again only because it’s 3 miles in and out on a dirt road and 20 mins to the nearest town with restaurant. But that’s a personal preference. The village and views are really beautiful so if you don’t mind the dirt road and drive then it’s the perfect place.

The stay at Tommaso's farm house was perfect! I would even so it was the highlight of our visit to Tuscany 🙌 Great location near Castellina in Chianti, which made it easy to pick up supplies and visit places nearby. The swimming pool and the view were also just perfect to hang out and relax. Recommend reading the check-in instructions before you get there so you check-in at the right place in town 😅 That was our small mistake, but the people at the hotel check-in were super friendly and helpful. Can totally see us coming back again. Thanks for such an amazing stay!

Fantastic couple of days in Panzano! The views are spectacular, such a beautiful place. Veronica is the perfect host, so responsive, nothing was too much. I wish we had stayed longer....... thankfully, there is always next time 😁

This airbnb is 100000/10. The view, the beautiful inside, the comfortable bed, and all the things to do nearby. It was such a beautiful and peaceful place to stay. We LOVED having breakfast on the balcony at sunrise and a glass of wine at sunset. All of the shops nearby are so cute and fun. I wish we could stay forever!

My parents stayed at Franco’s for the second time and loved it again. Franco gave great recommendations for the area and events that were taking place at the time. The accommodation was very clean, and the location is simply beautiful. You have everything you need, and it’s a perfect starting point for activities. Would highly recommend it. Thank you very much for the kind communication!

We really enjoyed our stay at this really unique accommodation. It is located in a medieval village, high on a hill. The apartment is compact, but has everything you need. The view from the balcony is fantastic. Malgorzata was a great host and very responsive when we had questions. I would not hesitate to recommend this property.

Paola is a great host! Everything was clean and perfect and the view was breathtaking! I 100% recommend!

Our stay at Luca’s place in Florence was wonderful. The location was extremely convenient with main attractions like the uffizi and galleria dell’academia just a short walk away. The apartment is also located in a very nice square that is lively and fun, but not noisy from the room. There are many restaurants and shops just down the stairs. The room itself was all that we could have wanted. The whirlpool tub was a very nice feature, the bed was conformable, and the atmosphere of the room was very cozy. If we return to Florence, we would love to stay at Luca’s place again!

Easy check in and out. Beautiful space and much bigger than expected. Great place to relax and explore if staying in the city. Really no negatives, book it and be happy.

This estate is a dream—life changing in all the best ways. From the jasmine-scented gardens and sweeping views of Siena to the beautifully restored guest suites—personally designed by Andrea, an architect and true artist—every detail felt magical. He greeted us so warmly, spent generous time sharing the estate’s history, and even gifted us a bottle of his family’s wine—which was absolutely lovely and made us feel truly welcome. The plunge pool was a refreshing retreat, and the setting was pure tranquility: birdsong, rustling leaves, and golden Tuscan sunsets. Andrea gave us a wonderful tour and shared the story behind his family’s efforts to preserve this incredible place. We adored the gentle Maremma dogs, Fiora and her puppy, Pecorino, who made us feel right at home. We were so impressed with this stay and Andrea’s efforts to preserve this very special place. Every moment here felt like a scene from a film—elegant, peaceful, and filled with soul. We can’t wait to return.

We had a wonderful stay. The patio and hot tub were amazing. Walk to everything. No need for a car. Lots of restaurants and attractions close by. Grocery store around the corner. Outdoor hot tub was lovely after a day of steps.

Excellent location and beautiful apartment. Easy to get in self-check in and good communication with the host. Great kitchen, stocked with all the hardware you need. Common area was comfortable for the 4 of us. The view is amazing. Balconies on the water with close up views of Ponte Vecchio. Definitely one of the best places we've stayed in a 20 day trip in several cities.

After another Airbnb mishap, Gianluca was so accommodating to allow to book and check in late last minute. He even met us there personally to be sure we got in okay. He even had the fold out couch ready with linens and provided a few breakfast items. The place was better than we’d hoped, location was fantastic, updated and perfectly clean! We would absolutely stay here again. This place will be one of the highlights of our trip!

We loved staying here and had the most fantastic time. They were super helpful and responsive to everything and we can’t wait to go back.