Search Chianti Region Villa Rentals from CA $2,109

"View and property were perfect and met expectations"

"It was absolutely marvelous. The owner of the property was so informative on places to visit, and places to eat etc. We had a wooden time and I would recommend that everyone stay here at least once in your lifetime."

"The biggest issue that I had was the information that I received about the bus was totally misleading . It says there is a bus down the street… it’s a 10-15 min walk. Oh and it only comes 2-3 times a day and forget about getting back there on the bus. So 1/2 of us came unprepared to rent a car. You must have a car unless you don’t plan on leaving. I can tell you a cab will come and pick you up, the one way trip to Santa Maria Novella is @ 70-80 euro per cab. We could fit 4-6 people and the fee...

"Enjoyed it"

"We enjoyed a delightful two weeks staying at Villa Il Borrachio in September. Apartment Azalea is spacious, well equipped and set on two floors. The two bedrooms on the first floor have double beds and en-suites whilst the bedroom on the ground floor has two single beds with a bathroom located on the other side of the kitchen/dining area. There is a wonderful view from the living room of the countryside with San Gimignano in the distance. The wi-fi was good and with our laptop plus hdmi cable we...

"Staying at a villa and property like this was a dream come true. As you’ve read the pictures just do not do it justice. The view is spectacular. Our host was so charming and helpful. We had a cooking class with Jacopo from "Let's Cook" which was so much fun. We also did a Chianti Wine and Food Safari with Walkabout tours that was fantastic. All of Caterina suggestions were so helpful even down to the drivers she recommended. Having this Villa to come home to each night was the icing on the cake."

"This villa is a dream. You really feel like you’re in a Disney castle in the home and in the little village! Our hosts were so easy to communicate with and so patient with us as we arrived much later than planned. They even went to great lengths to try and help us find food upon arrival because our kids were starving. It’s a fantastic location if you plan to take day trips all over Tuscany. It was nice to be centrally located so we could head out to Florence, San Gimignano, Lucca, and Pisa and...

"My husband and I and our young adult daughter stayed in Villa Clotilde, Strada in Chianti in early May of 2024.Communication with the host Francesco was great from the start.The home is beautiful, spacious and very clean. It is a qiet getaway in the heart of the Chianti wine region.The Villa is a great vacation home with great views of a valley, in a mountain range. The home is less convenient for transient traveler's as you have to bring everything. None of the essentials are provided such as...

"I don't have the words to describe how wonderful Villa Poggio is! The perfect location--just far enough from Florence to feel you're in the countryside but close enough that it's easy to get to. The villa is beautiful, inside and out, and each room has special touches to make it unique. We loved the outside spaces and had Prosecco on the terrace almost every night. The dining table is huge and we could all gather there each night to share stories and laughter. The views from one side of the...

"Our stay was amazing. The location was beautiful and easy for us to explore the surrounding area with ease. The house was beautiful, very clean and our host was most gracious. Upon arrival we had made a passing comment on how beautiful the patio terrace was and how a fire pit would be a nice touch so that we could enjoy it longer into the cool night. After the dinner our host organized for us at a local restaurant we returned to having a fire pit and wood on the patio. They went above and beyond...

"Really enjoyed the property and views. As an option, having Serena prepare meals was a great decision. She was just a fantastic as her cooking. The place was clean, well maintained and just what we were looking for. Owner was very helpful and responsive too. Definitely a property I plan to stay at again."

"I brought my family (5 adults with 80 y/o mother) to Italy for Easter Holiday. Property was beautiful, easy to find and to get to off A1 allowing us to get to many local Tuscany attractions. House was perfect for adults with ample sitting areas, large bedrooms and bathrooms. We enjoyed a wine tasting and dinner one evening in the property which we thought was outstanding, would stay here again."

"We thoroughly enjoyed this property .it is well off the main road , totally private, and the view is breathtaking .We are happy to recommend this villa to future travelers."

"Fantastic holiday in a beautiful villa.The property was fully equipped, well maintained and the big house was very well planned for a large family where everyone got their own space. Big rooms and very clean. Short drive to Florence. Everything was very clean. It actually looks far bigger and nicer than on the pictures. Fantastic pool, large. Thank you!"

"We absolutely loved our stay for a group of friends for a big birthday. the bedrooms were large and all perfect except the weird one with the twin beds. we added an amenity by adding a catered chef dinner one evening and it was 100% worth it - the meal and staff were amazing. great communication during check in and check out via whatsapp . wifi worked great. only issue was transportation - this home is not near the train station and there are not cars available in Certaldo . If you stay here...

"Villa Giotta was the perfect spot for our family trip. We stayed for 7 nights with 8 adults and 2 children. Lorenzo was very attentive to our needs and very helpful in finding transportation when we wanted to go as a group to Sienna. He also arranged a cooking class at the Villa which was a highlight for our trip. The property exceeded our expectations. It was beautiful inside and out. The pool was clean and the gardens were gorgeous. We were a 20 minute bus ride from Florence with a bus stop...

"This property was absolutely charming! I was impressed with the restoration of the property and the amount rooms available for our family. The outside sitting areas and pool are beautiful and the sunset and sunrise are breathtaking. We enjoyed the wine and olive oil produced on the property and the hospitality from Giampaolo. The kitchen is small to prep family meals but there are several local restaurants to have dinner. We want to go back!"

"Our stay at Gianmatteo and Christina’s was beyond our wildest dreams. As many other reviewers have noted here, the photos do not fully prepare you for the beauty of the property. There are stunning views in every direction you look and the only thing better than the views was the warmth and hospitality you felt from the hosts. Our word of the week was, “wow.” We’re still saying it now having returned to the states. There are a lot of beautiful places to visit in the world, Gianmatteo and...

"The views were beyond compare! Proximity to Castellina in Chianti was wonderful and the management team were responsive to a few issues. My main comment would be, especially considering the rental cost, that the furniture and kitchen supplies (dishes etc) needs upgrading and the quality of the beds/linens should be improved. Overall however, it was a lovely stay! Grazie."

"The location is really beautiful. There are constant shuttles to transport from one location to other within the property. Nice food options and music on specific days Clean Cabins If you have not booked shuttle from the Figline station to this place- you may have a hard time getting a taxi from the station. I recommend to plan ahead for the commute from the train station to this property."

"The staff is friendly and helpful. This is a nice place to stay . "

"We looked at many properties, both online and during a December visit to Chianti. This villa was by far best location we found. Everything was perfect, from our communication with Serena, to the reception by Raffaella, and then a stay in an amazing villa in an amazing setting. We were a group of maximum 9 persons, ranging in age from 20 to 60, and all were pleased with the amenities, especially watching the sunset across the vineyards and hills of Tuscany from the terrace. We will be looking to...