Family-friendly holiday rentals in Radicondoli

We absolutely loved our stay at Massimo's home. It is a peaceful sanctuary with stunning views of the surrounding vineyards. There is plenty of room for adults to sleep comfortably. Massimo and Beatrice were helpful with providing recommendations in the area for wine tours and restaurants and friendly to us during the stay. Highly recommend it for a homey getaway in Chianti!

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.

Cannot recommend more highly. A fantastic experience from start to finish. Helpful from the moment we booked to the moment left, including helping us organise lunches and wine tours. The villa itself is spectacular with stunning views of the Tuscan countryside. The villa was clean, spacious and charming with a bathroom for every room, fully equipped kitchen, games room, TV room and laundry. The pool is fantastic, as is the hot tub and the outdoor dining area and BBQ was perfect for everyone to eat, drink and laugh around. A truly memorable holiday at an unforgettable place

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!

What a fantastic find!! Bernadino and Edoardo were superb hosts at the beautiful house overlooking the vineyards. It had all the amenities you could wish for and was spotlessly clean. Edoardo cooked for us one evening and it was so delicious and reasonably priced. I would gladly have had her cook for us every evening!! A perfect stay, couldn’t have asked for more 😊

Lovely place I stayed with my friends. We all had a good time because the house is equipped with all the comforts both in the kitchen and in the rooms. A magical place

A peaceful and relaxing stay in the beautiful countryside. The unit is private & gorgeously renovated & bedroom overlooks vineyard. The hosts- Andrea & his brother were very welcoming, helpful and friendly, with lots of local suggestions. The main villa tour is also amazing. All in all a wonderful stay! Thank you!

We had the most incredible time at Cristina’s place! Her home is so beautiful, and surroundings are so picturesque! We enjoyed a cooking class with Cristina’s husband Carmelo and it was an incredible evening! She was so friendly and responsive. I hope one day we will be able to return to this incredible spot in Simignano!

Monica is very welcoming. The value for money is very good. Be careful if you have small children because there are slightly steep stairs to access the accommodation.

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

Matrace is of memory foam. I slept very well but just something you should know if you don‘t like this type of matrace. Extra blankets were there and overall super comfortable bed. Wifi speed was fine, not as fast as I would have liked. Host was really nice. We would definitely come back here! Use the app „easypark“ for nearby affordable parking on a „pay as you go“ basis. Shop im the nearby esselunga supermarket.

We were six adults, two children (3-year-olds) and one infant staying at the house for a week. It’s located in a secluded spot with a large garden and beautiful views of the Tuscan landscape. We used all of the five bedrooms upstairs and they were dark and cool. The kitchen and living room downstairs also stayed cool. Right outside the kitchen there’s a really nice spot that’s in the shade for the most part of the day, where we had most of our meals. This is a great place to relax and enjoy a dip in the pool. However, you definitely need a car to get around. The gardener came around several times a day to maintain the pool etc. We appreciated this, but might be good to know if you’re looking for complete privacy. We also had some issues with the bathrooms; one toilet and a shower didn’t work properly but were fixed within a day and this didn’t affect our experience. The washing machine didn’t work despite repeated attempts by the host to fix it. The barbecue is in the trash room.

Claudia is a great host, always very helpful and super nice. We felt very comfortable. The apartments have everything you need, the pool is great - very clean and with a wonderful view. The location is also great - in about 15 minutes you are in the Volterra and up to San Gimignano you only need half an hour. We will be happy to come back and thank you for the delicious oil and the nice holiday!

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!

Lucia and her husband are wonderful hosts, warm and kind-hearted. Their home is truly magical—clean, spacious, and cozy. We felt so welcomed and comfortable throughout our stay. Highly recommended!

We had a lovely time with Cristiana and Sergio. The apartment "La Margherita" was very clean and spacious. The children enjoyed the pool and there was plenty of room for everyone. We received helpful tips and Cristiana was always open to questions and responded very quickly. For chess lovers, there is a beautiful board in a great location. Highly recommended!

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!

Spacious and isolated house, perhaps to make the most of the experience it is better to take advantage of this accommodation during the summer. Ideal for groups of up to 16 people (to reach 20 seats you need to use two sofa beds). Very friendly and helpful host. In general I am very satisfied with my stay, the only negative note is the additional €100/night for heating costs, I would have preferred to pay based on what was actually consumed.

The place is magnificent and very well kept, clean and super cozy. It's a little out of the way but we chose it just for the secluded location and surrounded by nature; in any case with a halfhour by car you can get to several wonderful places. Nicola was very kind and helpful. I highly recommend a stay here, it's refreshing!!

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!

Fantastic accommodation with lovely views of the countryside. Especially loved the fire place and large spacious kitchen. Charley and Ann were very gracious hosts and I would have no problem recommending this accommodation to anyone who wants to visit Tuscany. The accommodation was within 30 mins of most tourist towns and trains which made it excellent for day trips.

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!!

Great location - close if you are flying into/from the Florence airport - extremely close to to Villa Antinori - Dario Ceccini in Panzano - San Gimignano - Siena, etc. Pictures are representative of the apartment - grounds exceed the pictures. Grounds are very well maintained. The pool is exceptional. Great cats and dogs to welcome you throughout the day. Kitchen is very workable, knives are sharp, gas stove and kitchen utensils are stocked and ready for your carbonara or amatriciana. Plenty of staff is located on premises but are not at all intrusive. 11 out of 10. Will return.