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 beautiful haven of beauty and silence. Staff hyper .merci a landreana more particularly . 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!

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!

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.

An amazing stay! The location was perfect for exploring Tuscany, and the view was incredible. The terrace was an ideal spot for relaxing.

"Charming Jewel" is squeaky clean and centrally located within easy walking distance of popular historical sites, as well as high-end shopping. It is tastefully furnished and includes lovely kitchen supplies and ample towels. My favorite aspect of "Charming Jewel" is the tall and expansive windows. In terms of communication, Riccardo is efficient and attentive. "Charming Jewel" is the peaceful, luxurious retreat I will now recommend to fellow Firenze travelers and where I'll stay when I return!

The perfect place to explore Chianti each day. We stayed 5 nights and it was just perfect. Great amenities, beautiful pool, bbqs and lovely areas to sit and enjoy the views and the sunset. Always fabulous to come home to. Our upstairs apartment was spacious, comfortable and all we required with a lovely view. We had great recommendations from Silvia which we followed up on. Great to have restaurants nearby. Reasonable- highly recommend.

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.

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.

We had the most amazing stay at Sibilla's apartment! It is STUNNINGLY decorated and almost makes it feel like you are staying in the Medici Chapel itself. The apartment had everything we needed, and the plant room/ sunroom was glorious to enjoy in the mornings/returning after a day's exploring. We met both Niccolo and Sibilia and both were so friendly and helpful. The area surrounding the apartment is perfect, with central Florence being a 20 minute walk away, and the restaurants/shops/wine bars of Santo Spirito being literally on your doorstep. This is the most enjoyable Air BnB we have ever stayed in, and would come back in a heartbeat! Grazie mille!!

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 😁

our stay here at Marios was utterly magical. the family who runs the day to day operations are so friendly, accommodating and a real pleasure to be around. the food was out of this world fantastic. my son loved the pool and table tennis. the air conditioning was nice and cool. the al fresco dinning was phenomenal and so peaceful yet bustling with others enjoying their vacations. Just book it. the price was fantastic, the coffee food and company even better.

What an incredible location!!! Monticchiello is the most quaint and picturesque town nestled in the heart of Tuscany. Walking up to the accommodations feels like a fairy tale - the view of the Val D’Orcia and the medieval tower you walk into, but you are then transported into the most relaxing little apartment. The amenities are wonderful - the attention to detail was not lost on us. We stayed here right after our wedding and it was exactly what we needed. Also, Deb’s Lounge was such a nice place to get breakfast (included!) and we enjoyed some fresh pici pasta for dinner our first night. Would 100% come back!!

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.

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.

Apartment as described. Very clean and comfortable. The center is a 10-minute walk away. Always top-notch and very kind communication. When I return to Florence, if there is the possibility, I will return to this apartment.

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.