House vacation rentals in Gaiole in Chianti

We had a wonderful stay at this property which is a bit difficult to reach, but is more than worth the painstaking arrival. The fantastic location is simply breathtaking – expansive fields lined with cypresses and olive trees create a backdrop that looks like a Tuscany picture book. The hosts were extremely nice and charming. They provided us with great tips for excursions and activities in the area, which has enriched our stay. Particularly noteworthy is that our dog also felt very comfortable and we could thus enjoy relaxing time as a family. In summary, we can recommend this place to anyone who wants to experience the true beauty of Tuscany. A place to relax and enjoy – here we will be happy to come back.

We had a great stay in Florence, Simone was very nice and we could check in even earlier which was very nice and made things easier for us. Simone also inquired about our well-being during the stay. The parking space is still on the property but there were many possibilities to park in the immediate vicinity.

We had a wonderful week here. It was baking hot but the pool, the shady garden and the air conditioning made it the perfect peaceful place to relax between Rome and Florence.

Lovely place to stay and great welcome! Everything was clean, cozy and convenient, fully consistent with the description. The neighborhood is calm and easy to get to everything. We especially want to note the host — Harry is just a super cool person! Very friendly, open-minded and helpful. He met us in person, showed us everything, helped us navigate, gave useful advice — there was sincere attention and care. Thanks to him, the vacation was even more pleasant. Recommended to everyone! Everything was at the highest level, definitely five stars!

I had the most amazing experience staying at this beautiful villa in Florence. The location was perfect—peaceful, private, and surrounded by stunning views that took my breath away, especially from the parking area. The villa itself was incredibly cozy and charming—so well maintained and full of character. Honestly, I didn’t want to leave. I’d live there if I could! The pool was a dream—relaxing, and the perfect spot to unwind with the Tuscan countryside all around you. Our host, Leonardo, was absolutely fantastic—so friendly, welcoming, and helpful throughout our stay. You can tell he really cares about making guests feel at home. This place was everything I hoped for and more. I would 100% come back again. Highly recommend!

Everyone was wonderful, the accommodation was as described and the pool completely to ourselves. Giovanni was always super friendly and his family very accommodating. We would definitely recommend this place.

Gina’s place is absolutely phenomenal. Stunning, out of this world location and a very comfortable villa. Gina was an amazing host who welcomed us personally and showed us around. We had a good basket and freshly cooked food as a welcome gift!! I cannot recommend Le Capanne highly enough. It was awesome.

The stay "Casa Elisa" was better than we expected. It is a large house with even a basement with sauna. The pool in the garden (with outdoor shower and toilet) and the house itself were sparkling clean. There was no dust or cobweb to be discovered (not even behind a closet that we moved to be able to reach an outlet). The view from the balcony was breathtaking and the surroundings were fantastic. You are so in towns such as Siena, Arezzo, Perugia and there is also a large lake nearby where we rented a boat for a day (recommended). In short, we can recommend everyone to book with Lorenzo. The communication with Lorenzo was also excellent, easy to reach via app and speaks good English. His father comes to check and clean the pool every day and his mother's day baked a delicious cake very sweetly.

Alessandra’s place was an absolute dream. It’s picturesque with the most gorgeous view of Tuscany hills in a rustic styled rental. She was extremely helpful and attentive during our stay! Would definitely come back here next time we visit!

we had a very nice stay. The whole place was very clean. Highly recommend taking something against the mosquitoes. the only criticism was the chairs on the terrace, as 2 have shackled heavily, there should be a replacement here.

Great location and the 2 full size bathrooms were nice!

Had a week here with good friends. Enjoyed the beautiful house and the area. Great for a slow, calm getaway!

Great place in gorgeous surroundings… Nice small old house in a charming little village. Eugenio gives clear instructions and takes care of the needs of his guests. Warmly recommended!

We had an incredible stay at this beautiful villa in the rolling hills of Tuscany. Perched on a mountain, the property offers stunning views over the countryside, with gorgeous gardens and an authentic Tuscan feel throughout. The villa itself was spacious, comfortable, and full of charm. The location was perfect — peaceful and private, yet central to many of the places we wanted to visit, including Florence, Montepulciano, Siena, and San Gimignano. Christina, our contact person, was a great communicator. She was also on time, very helpful and pleasant to be around. She provided us with great insights about the area and the property. The location was excellent for us to use the e-bikes that we rented. We had breathtaking rides around the area. There was an excellent grocery store, Conrad’s in Bucine with a very tasty restaurant in the same Plaza. It was the perfect rustic home base with lots of charm the Tuscan experience for exploring the region, and we would absolutely stay again

We had a wonderful time in Vittoria's house in this fantastic location. Although we had so many difficulties getting there and only arrived at night (flight delayed and highway closed), her husband greeted us very kindly and showed us around the house. Vittoria was always super quick to respond and always helped us (e.g. turned on the heating when it suddenly got cold). Highly recommended!

We had a fantastic stay with a group of four adults and five kids. Accommodations were immaculate, private chefs were decadent and delicious, and fantastic wine. The grounds were just lovely as well and we enjoyed having a fire in the fire place every evening. That you for a lovely stay!

We had a perfect break in Lorenza’s lovely house. It was extremely spacious and exceptionally clean. The garden is beautiful and well maintained with lots of areas to sit in and enjoy the peaceful environment. Our dogs loved their walks in the woods nearby and they enjoyed meeting all the feline residents! Lorenza and her husband are a lovely friendly couple who have put a lot of thought into ensuring their guests have a great holiday.

Absolutely stunning views and a beautiful, well appointed home! We loved our stay here and found Suzy to be incredibly friendly and helpful! We would love to stay again and highly recommend.

Romantic Alcova a stone's throw from the city center but with the qualities of the country house, quiet and retired. Beautiful structure where we spent a week relaxing and that we used as a base to visit Pistoia and the Apennines. Mrs. Gianna is an impeccable guest. I recommend it

Joy (the owner) is a joy! She is one of the best hosts we’ve had on this platform. Flexible checking, due to delayed flight. Rooms were bigger than anticipated and beautiful. Lovely rustic Tuscan charm of a property. Plenary of recommendations at the property for local restaurants and activities. Can’t recommend this property enough!

we immediately felt comfortable 7 d enjoyed the stay very much. A ideal starting point for excursions.

We stayed in this beautiful Tuscan villa, completely in authentic Italian style. The house is in a brilliant location with views over Montecatini – in the evening a sea of lights! Due to delays on the way, we didn't arrive until 11 p.m., but that was no problem for Cristina. She kindly waited for us and took plenty of time to show us everything. Cristina is an excellent host and communication went smoothly and pleasantly in English. The villa is very private, with a large enclosed property and a fence all around. Parking is available on site. A little tip for future guests: Don't blindly follow your route planner. It will send you via a narrow winding path that you can hardly cross with one car. Preferably take the route through the other side. The swimming pool is tastefully lit in the evening and the surroundings offer plenty of beautiful trips to towns such as Lucca, Florence, Pistoia and Siena. We'd love to come back!

This is a beautiful home in Tuscany and Nada is a lovely host. We will definitely come back!

The terrace was great, and the entire place had a quiet and peaceful feeling.