Villa holiday rentals in Gaiole in Chianti

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 🙏🙏

Our family had an amazing stay. Beautiful location in the hills with an easy drive to the center of the city. The property is optimally set up for a large family gathering, and the pool area was perfect . We took advantage of the tasting and the cooking class , and both were executed perfectly . A completely memorable trip with great wine, food and views. Marta from the property management was incredibly responsive and friendly .

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.

The villa has an Old World vibe, but with modern amenities. It was a great place to stay and cook and dine. This was a nice location to base our Tuscany exploration from. The hosts helped facilitate a wonderful home cooked meal by Vilma upon our arrival. The hosts were also very responsive to our questions before and during our stay. You will love this villa!

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!

We (7 girlfriends) enjoyed the stay in the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She has sent us a lot of tips about the area (also the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed anything, there was a very quick response. The villa is well equipped and the surroundings beautiful. Parking has enough. Only the potholes and the access to the villa are a bit challenging - but doable!

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.

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 had an excellent time staying at this family home with an amazing view of Torrita di Siena. Great access to many popular hill towns (Cortona, Montepulciano, Pienza, Montalcino, etc). The house and property are beautiful, very private and populated with song birds and olive trees. The hosts are charming and very welcoming. They provided us with all the recommendations we needed and were readily available whenever we wanted to communicate with them. The house is well appointed and has multiple ways to cook from gas range to pizza oven and wood fired grill. I really liked using the giant pinecones as fire starter. We would definitely return and hope to. Such a precious slice of paradise.

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 🥰

Thanks!! We enjoyed our vacation with 9 girlfriends! A little humidity due to the weather, but the place is ideal in summer and comforting by the fire when the good weather is not present!

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.

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.

Francesca’s home was beautiful and in a breathtaking, peaceful location. There is a short, beautiful walk with Mountain View’s and olive groves to an incredible pool and pool house. She was incredibly helpful in helping us not only access the home, but also in providing us local recommendations. The meal that Ettore prepared for us was one of the highlights of our trip.

This was a beautiful farmhouse tucked away in the hills behind town. Very beautiful place. My family and I really enjoyed our stay.