Family-friendly vacation rentals in Gaiole in Chianti

This was our second time at Il Vichiaccio and I hope it's not the last. In fact, this Airbnb is the entire reason we had Tuscany on our trip itinerary. Beatrice and Massimo are the most wonderful hosts in the world. Besides simply being great people to chat with, they are hospitable in providing some of their homemade wine and eggs. There's nothing more special than relaxing in the hot tub with the vineyard views and walking up the hill to dinner at Il Cavaliere in the castle. Our only complaint is that we did not see the kitty cat this time! She was our favorite host when we visited 3 years ago. Oh well, I guess we'll have to book again soon and try once more :)

The house is so nice, clean and cozy. Daniele gives us many helpful tips and place to go, very nice and proactive host.We enjoy our stay very much thanks to Daniele. The place is peaceful and easy to go anywhere, Pisa, Lucca, Florence and Cinque terra. Such a lovely house , highly recommend for family trip👍🏼

We had a very pleasant time here. Carlotta was very friendly from the start, and even recommended local grocery stores. This place is a hidden gem! You are surrounded by beautiful trees & nature, but close enough to the town where you can easily catch the train to Florence. We absolutely loved it!

We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!

We had such a lovely stay at Bernardino’s villa! He greeted us when we arrived and made sure we had everything we needed. The home is very charming and peaceful, and centrally located to explore Tuscany. Would definitely recommend!

Massimiliano is a great host. Lives in the apartment next door so very easy to get inside and readily available to help. The apartment has a bit of that old school charm that we personally enjoyed. Clean apartment, clean bedding, bedrooms are good size (one bedroom with large bed, fit two adults and a baby), and the other bedroom has three single beds. The living area has a small couch in it (fits two adults max) and a small TV. The only two things I would advise on are that the elevator doesn’t work to get you to the third floor, so be ready to carry your luggage up two flights of stairs. The second, floor is screeching in the living area anytime you step on it. Didn’t bother us, but flagging for you. Finally, the location is about a 10 minute walk away from the actual city centre. Again, not a big deal for us since we are a young active family but just to make you aware. There are some amazing coffee shops along the way though so we did enjoy the stroll. Overall great stay, thanks!

Beatrice was a wonderful host and accommodating of our needs traveling with a two year old. She was very responsive and gave amazing recommendations for places to eat and visit. The location is stunning - even more beautiful than the pictures! Every direction you look has rolling vineyards. We opted to have them cook a special birthday meal one of the nights, and it was delicious. The only small downside is there isn’t a common area to spend time in besides the kitchen (just the layout of the house). We loved it and hope to come back some day!

The property is stunning and a very quiet rural setting. The view is spectacular. At night you can see all the stars. The beds and pillows are comfortable. The house is very clean. Andrea gave us a personal tour of his home and his family history is amazing. We thought it was a very personal touch to greet us at check in. He also called the day of our departure to say goodbye and came to the house for another short conversation. Andrea gave great recommendations for food, groceries, tours, etc. the location of the Airbnb made day trips very convenient. We would definitely come back. We felt refreshed after a few days. We also loved his two dogs!

Really enjoyed the stay: the place is spacious and cozy (even more beautiful than in the pictures :)), there was everything you need: bed linen, towels, everything equipped with kitchen. The hosts are friendly and although they don't speak much English, but they explain everything:)... The town is charming too - full of historical buzz. There is a small thermal spring quite close (from the property maybe 5 min walk) - quite hot so only one of us bathed, but our feet were all soaked;)... We had a wine at the townhome's bar - it was very nice to interact with the locals. Literally, the warmest feedback - thank you for everything!

Had all necessities needed. Helpful neighbors with check in and check out. Good location with free parking!

We had a fantastic experience at Stefania's place! It's a beautiful studio which was spotlessly clean and has everything you might need. Slightly out of the centre of Florence (in a lovely area, we recommend the walk from the flat to Piazzale Michelangelo for stunning views) but you can get the 11 bus into the city. The bus isn't always reliable on weekend and evening so we often walked back to the flat, the hill looks intimidating but it's a relatively easy walk. Stefania was very responsive and had good recommendations for us. There is also a super cute cat in the building that was friendly.

Marina's place is one of the most beautiful places I've ever seen. The attention to details, the amenities and her communication made our stay very relaxing and enjoyable. Thanks Martina for a great stay in Tuscany.

Clara was a wonderful host and very polite. He waited for us to give us the keys and explain everything in detail inside the apartment. The apartment was beautiful and made us feel at home as it had everything needed. He even left us two large bottles of water on the fridge. Cafe y te yemos as if you were coming back your house. Highly recommended.!!!!We'll be back!!!!

We loved our stay at Giulia’s - it was like home from home and had everything we needed. It has beautiful surroundings and is great for cycling! Giulia was very helpful with recommendations and friendly too.

A truly stunning place with incredibly welcoming hosts. The villa exceeded our expectations in every way. The interior is filled with beautiful historic furniture, details, paintings, and books. The cozy fireplace in the living room added a special charm. We loved making pizza in our very own wood-fired oven, using the outdoor BBQ, and dining al fresco surrounded by breathtaking views. Every moment at Poggio del Fattore felt special, offering the perfect blend of comfort and authenticity. Highly recommended for anyone looking to experience the beauty of the Tuscan countryside in style!

This was exactly what we were looking for. Very peaceful and private with beautiful views. Lots of wonderful villages to visit and explore within a 30 minute drive. Norma made some great reservations for our anniversary dinner as well as a couple of great wine tours. She also gave us recommendations of which villages were best to visit and what to do there. We highly recommend doing the cooking lessons with her family. They are such a nice family and were very eager to show us how to cook a traditional Tuscan meal. Grandma really is an amazing cook. They even sat with us as a family to share what we had cooked. We have been to many AirBnB’s and Norma has been our best host by far. We would go back the next time we visit Tuscany. Dave and Liz

We booked Villa Montechiarone as part of our wedding at Montechiaro Organic Winery to house a group of 7 guests. The property sits around 500m from the winery itself, with views out over the Tuscan countryside, it's a breathtaking location and the villa itself is an incredible space. There are 2 huge indoor living areas, a well equipped kitchen, 4 spacious bedrooms and an outdoor covered terrace, as well as the garden and pool area. There is real character in the property in the way it is decorated as well as the imposing facade of the building itself. The pool area is spacious and well placed to take in the most of the view, and there is a car port with parking for at least 4 cars covered, with plenty more room if required beyond. Overall perfect for housing our guests who had a great experience and were very thankful for the help whilst checking out also!

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.

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 farm and very competent and available host. Definitely recommended

For our family vacation, three couples and a 1-year old, the place was perfect. The ability to spend the heat of the day in the huge pool or inside the refreshing lodging made the stay excellent. The place is close to groceries, pharmaceuticals, restaurants, local sites, cities, etc. Ken was always responsive to whatever issue we brought up and his quick replies were greatly appreciated.

Cristina is the ultimate host! Everything was immaculate and set up for us. We traveled with two young kids, and she was proactively prepared with a crib & high chair. She also had amazing recommendations and answered any questions for us. Led us to a spectacular sunset winery in the hills. The premise has stunning views and hanging poolside in the mountains, was just what the doctor ordered. Highly recommended and makes you feel like family!

Sabrina and her family were very accommodating and amazing host! The whole stay was superb In every way and my whole family as well as myself noted it couldn’t have been a better experience. From the amazing home cooked breakfast, to the cleanliness of the house, and the well thought out and led cooking class/dinner we enjoyed every aspect. Sabrina was very welcoming and made you feel like family :) I would highly recommend to anyone looking for a peaceful farm style stay that wants to experience Tuscany.

Paula has not only created a beautiful sanctuary that perfectly reflects Tuscan culture, but offers wine tasting and a vineyard tour on her property. The location of this gem of a place is centrally located in the Chianti region , making it a perfect home base for day trips to Assisi, Firenze and nearby small villages that offer great restaurants and quaint shops. The region is cycling friendly, as well as offering places for day hikes. Staying here for five days was one of highlights of our Italian adventure.....and we highly recommend experiencing the perfect place to stay in Tuscany and the warmth and friendliness that Paula, Ferderico and her staff offer!!