Villa vacation 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.

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

Brigitta's place was stunning! It was extremely private, peaceful, and absolutely beautiful. The pool and hot tub were wonderful, and the surroundings were very calming and quiet. The house is clean, warm, and we felt right at home. It's a 10 minute drive in to Gaiole in Chianti, which has great restaurants, and a short drive to everything you need in Siena. It was a great location for day trips all over Tuscany. Brigitta was an excellent and lovely host! She was super friendly, quick to respond, proactive, and made sure we had everything we needed. We had a great time and can't wait to come back! Highly recommended!

Oscar was very friendly and kind to us! His house is beautiful and comfortable, we were in a group of 13 and we were quietly staying. Beautiful decorations and landscapes. Note 10.

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.

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.

What an amazing getaway from the busy parts of Italy! This villa is more than you can imagine, with a beautiful view, phenomenal pool, big kitchen, and many private rooms. The lovely smells from the garden, particularly the rosemary, added a great touch!

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 lived staying at David’s cost farm house. It’s been artfully restored and the surrounding scenery is just breathtaking. We were greeted on arrival and had a lovely welcome gift waiting for us. There was ample space for four of us. The downstairs bedroom was perfect for my in- laws who had step free access to the garden directly from the bedroom. David was always responsive and helpful, especially when navigating Florence’s tricky parking rules. I would definitely come back again when it’s a little less rainy to fully enjoy the outdoor amenities. But for now Ciao!

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 spent a week at Villa Poggio a Mandria as part of a group of six adults and had the most incredible and magical time. The photos do not do justice to how extraordinary the villa and surrounding area are — it’s nestled in an olive grove near the top of a hill just a short walk from a medieval village (Montegonzi), with utterly spectacular views in every direction. It could not be more peaceful or breathtaking. The villa was spotless, gorgeous and fully equipped, with tons of space for everyone. We had an unforgettable day with Lorenzo (contact available through Claudia and Leonardo), a local tour guide and chef who took us on an amazing wine tour and then cooked us the best meal ever that evening. And Claudia and Leonardo are the kindest, most responsive hosts, always available to answer any questions we had and even baking us a beautiful cake one evening! We can’t recommend Villa Poggio a Mandria enough. We had an unforgettable trip that truly felt like a dream. Thank you!

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!

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 wonderful stay in Tuscany, largely thanks to this beautiful house and its amazing site. The facilities are perfect and allow you to spend beautiful moments with family, but also for everyone to have moments of tranquility (we were 6 : 2 adults and 4 teenagers). The site is perfect and exceeded our expectations in all: nature, the view of the landscape, the pool and outdoor facilities, the character of the house both inside and out. We were well received and advised by the hosts. We would definitely and enthusiastically recommend this home!

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.