Villa holiday rentals in Gaiole in Chianti

The stay was beautiful! The villa was amazing, the view, the furniture, the rooms and the pool. We felt so lucky to be there. Rooms were new and clean. Every detail has been taken care of. Christina was incredibly helpful and always available. We'd be stuck without them. Unfortunately, we had more private problems and every time she helped us and brought us solutions. We, me and my friends, this stay was memorable!

Five friends made to feel very welcome to this beautiful spacious villa with a lovely pool set amongst olive groves. The scenery that surrounded us was beautiful. Invited to Mark's villa who shared his knowledge and history of the olive groves which was very interesting and the hospitality received was first class (vino and yummy bruschetta's). This was the perfect place to stay and would highly recommend.

Great stay in a lovely remote area. The pizza oven was a major highlight

Fantastic all around experience. Thank you Elio and team 🙏🙏

Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!

Our stay at Terra Antica was a dream. The location is perfect and the property and villa are exceptional. We were close enough to town to get to restaurants and shopping and then come back for some quiet relaxing time. There are numerous wineries to visit in the area. Day trips to other local towns are easy to do as well. The private jacuzzi was an extra bonus & we used it several times during our stay. We will be back again!

Stunning villa in a beautiful setting. Francesco gave excellent directions & the peace & tranquility out in the Tuscan countryside was wonderful. Francesco was exceptionally responsive & gave great local advice. We loved the little towns nearby and can’t wait to return soon. Highly recommended. Jack.

A beautiful property in a stunning location with great views. The property was easy to find using Waze. Once inside everything was clean and all rooms were luxurious and clean.

Villa Angiolina is truly beautiful!!! The view is incredible and everything was spotless and beautifully decorated. Our host was lovely and gracious and responded very quickly to all communications. She even arranged for an amazing pizza party with a private chef that was just one or the memorable moments from our time at the Villa. If this Villa is available…just book it!!! You will be glad that you did!!!!

The villa was perfect for our family of 6 adults and 4 children. Swimming pool with toys outstanding. Pizza oven and bbq fun to use and a beautiful peaceful garden. Walking distance into Castiglion which is a beautiful old town. Would love to return.

Absolutely gorgeous and luxurious place. Beautifully decorated, beautiful views, clean and also had an incredible kitchen. We loved it!

We had an amazing time staying at La Fonticina. Such a beautiful house and location, which came with everything that we needed. Cesare was a fantastic host and made our stay even better. He couldn't have been more responsive, accomodating and friendly. Highly recommend and wouldn't hesitate to return!

Had a lovely week at the villa. Amazing place and beautiful views! Florence a short drive away, but we also enjoyed walking about 35 minutes to Fiesole for restaurants and views.

We were a group of 32 with young to older childern. What a wonderfull stay. The Hostess was very friendly and helpful. She was always reachable and was always ready to help with questions or recommendations, writing often about interesting events, markets and towns to visit. She also gifted us 2 Evening meals which were both very tasty. The House was amazing, had everything we needed, was clean and had a lot of space. One could see that a lot of love and thought went into this house. The Location is beautiful, in a very small town in the hills of Toscany, 10 min from Pratovecchio which has a large grocery, petrolstation and smaller cafès. If you want to relax, enjoy the food, wine and countryside Toscany has to offer, this is the place for you. There is really nothing negative we can say about our stay there. The House and Hostess were amazing.

Our family enjoyed our stay at the villa very much. Our only regret is not building in more time to simply enjoy the beautiful surroundings and amenities the villa provided. Our favorite day was the vineyard tour, personally coordinated and led by Francesca. We visited two local vineyards in the Chianti region, received wonderful tours and explanations of the wine-making process, tasted fabulous wines, and enjoyed a spectacular meal prepared by Elena, with almost all ingredients sourced from her farm and vineyard. Francesca provided excellent guidance and advice as we planned our trip, arranged for drivers when needed, and was very responsive to all of our requests. One note of caution - the mosquitos in the evenings at the villa are pesky, so bring your bug spray.

We had a marvelous stay at Villa Sestuccia. The house is spacious, as are the grounds. Both are well maintained. There is ample room with different areas to relax indoors and outside. We communicated with Briggita who was quick to respond, always friendly and always helpful. We particularly liked the location which has easy access to many spots of interest and restaurants. We enjoyed collecting eggs in the morning for our breakfast - such a fun touch. We highly recommend Villa Sestuccia and would not hesitate to stay here again.

This villa was absolutely perfect for what I was hoping for. It was even better than the pictures, and the surroundings were beautiful. We loved the secluded feel of the villas, and the size of the villas was perfect for our group. Serena was super helpful and very flexible, so I can't recommend this place enough!

Alex, u show such hospitality to our family!! We love how well u maintained the place. The view from our hotel brings smile to my face every morning! It’s spectacular. I’ll definitely come back! Hope the price is reasonable the next time 🥰

This an absolutely wonderful house with so many qualities inside as well as outside. Extremely well decorated and dreamy wonderful house inside, superb and beautiful views outside in a big and calming garden. Janine is fantastic, super friendly and extremely helpful. We forgot our passport and it was brought to Florence. This is just one example. Nothing to add, amazing to stay here.

Great place with lots to do. Amazing views. Host was very responsive.

We had a wonderful stay at the villa in Tuscany and felt at home right away. The hosts, Silvana, Iacoppo, and Bruno, took excellent care of us and were always attentive to our needs. The villa itself is spacious and well-equipped with everything one could ask for. The beautiful pool with its stunning views and the cozy fireplace area were definite highlights. It was the perfect place to unwind and enjoy the Tuscan countryside. Thank you again for an unforgettable stay!

Beautiful house in the vines surrounded by sumptuous hillsides in an incredible postcard setting. Perfect for gatherings for families or with friends. The location is ideal to radiate between Siena, Florence and Chianti or resting while enjoying the pool. Elisa, always attentive, is very responsive and will respond almost without delay.

We had a great time. Everything is taken care of in the smallest details. Great for spending a weekend with friends. Looking forward to coming back in the summer to enjoy more of the outdoor spaces!!

Wonderful place to surround yourself with nature & getting away from the crowds. Quiet. Peaceful. Warm. Beautiful. Comfortably fit all of us. 5 including two young adults. Will definitely book again and be better prepare bringing all essentials to my stay as the town is like 15 min drive through small roads. Thanks for such a beautiful place for our Tuscany experience.