Family-friendly holiday rentals in Certaldo

Everything was great about the stay! We were really starving the day of ur arrival and Francesca was able to bring us some food for her that was all needed to kick start our day!

If I could move in here permanently, I would. What a gorgeous stay with responsive and respectful hosts. Everything was as described, the hot tub was glorious, and we loved looking through the binder of photos of painstaking restoration over the years.

We had a truly wonderful stay – for all five of us! The house and the outdoor area were absolutely beautiful, even better than in the pictures. Everything was spotless, charming, well maintained, and well equipped. The garden was stunning, and the whole place felt peaceful and private. Ilaria and Francesco were the kindest hosts – helpful, responsive, and incredibly welcoming. We’re already thinking about coming back for a summer holiday (the pool and AC are perfect!). Great location for day trips to Pisa and Florence, and there are lovely restaurants nearby. It was an amazing birthday trip and really good value. We wish Ilaria and Francesco all the best – thank you so much for everything! ❤️❤️❤️ Katharina & family ❤️❤️❤️

I can not say enough about Alessandra and her amazing land! It was the most magical place we have ever been to. We are taking a 3 month trip, hitting up 21 cities in Europe and this is BY far the best! She was so kind and took us shopping and back to our train! She was always there when we needed her.thank you Alessandra we will see you next year!

What an amazing place! The views across the Tuscan hills are some of the best I’ve ever seen. Amazing little secluded spot with lots of space for two couples. Sara was great and super helpful with everything. Would 1000% recommend this place

Beatrice was an amazing host. She was very responsive to our questions and always very helpful with suggestions and recommendations. This was the perfect place for our group of 8 adults for 2 weeks. The location was perfect for visiting various sites around Tuscany. Florence, Cortona, Siena and Pisa. The nearby town of Greve had some nice little restaurants for lunch/dinner. After a long day of sightseeing we would gather on the patio to have charcuterie and wine. Or gather at the family style dining table each evening. We highly recommend having Beatrice provide a home cooked meal, it was excellent! There are several wineries and olive oil tastings in the area. We took advantage of many of them. Overall we were very happy and very comfortable with our stay. We highly recommend staying here. If we ever come back we are definitely staying here again. You'll definitely get the true feel of Tuscany.

This estate is a dream—life changing in all the best ways. From the jasmine-scented gardens and sweeping views of Siena to the beautifully restored guest suites—personally designed by Andrea, an architect and true artist—every detail felt magical. He greeted us so warmly, spent generous time sharing the estate’s history, and even gifted us a bottle of his family’s wine—which was absolutely lovely and made us feel truly welcome. The plunge pool was a refreshing retreat, and the setting was pure tranquility: birdsong, rustling leaves, and golden Tuscan sunsets. Andrea gave us a wonderful tour and shared the story behind his family’s efforts to preserve this incredible place. We adored the gentle Maremma dogs, Fiora and her puppy, Pecorino, who made us feel right at home. We were so impressed with this stay and Andrea’s efforts to preserve this very special place. Every moment here felt like a scene from a film—elegant, peaceful, and filled with soul. We can’t wait to return.

Both Barbara and Andrea were very welcoming and forthcoming when we encountered a hitch in our travel plans. They are unusually friendly, and accommodating hosts. The house is a great base for exploring the surrounding area and is tastefully decorated. Highly recommended!

We loved staying here. The home is a very drivable distance from Florence and the surrounding Tuscany area, and the views were amazing. We took their recommendations for nearby restaurants and wineries and were very impressed with all of it. Host was very responsive and helpful throughout our communication.

Wow-10 days spent at Alec's villa and could have stayed longer! The age and beauty of this place makes you feel transported back in time. From the stone walls, the detailed wall paintings, furniture and decor, to the solid doors easily hundreds of years old... We spent hours just speaking of it's history. The house is clean, spacious, and had plenty of room for our family of 8. It is situated on a small family vineyard at the top of an incredibly windey road. There outdoor space was safe/secluded for my kids. The hill made for wonderful beautiful views and sunrise. However, as with much of Tuscany, we were glad our rental cars weren't too big! The closest town is 5 minutes away and has a few restaurants... Though not somewhere you can have coffee or walk the streets. About 15 minutes away is San Casciano where you can find coffee shops, restaurants, stores etc. Alec is a perfect host... helpful, responsive, and answered dozens of questions weekly. Book dinner at A Casa Mia for sure!

A beautiful apartment with stunning views. Easy access to many beautiful places to visit such as San Gimignano, Florence and Sienna. The apartment was clean and comfortable with amenities as listed. The views from the communal terrace were stunning and there was plenty of space to sit without being on top of other guests. We would highly recommend.

This is a dream location. In the countryside, peaceful and calm with beautiful views - but you can be parked and in the centre of Siena in 15 minutes. Beautiful Tuscan architecture and stunning views. Everything was super clean with every detail thought of to make a comfortable stay. We stayed for two weeks and didn’t want to leave. We had a car so access was easy but if you want a short stay I would recommend getting a taxi to drop you off and enjoy the peace and views.

Our Villa in Montespertoli was everything we could have wished for and more, full of all the modern conveniences required to cook if desired. The grounds were absolutely delightful and the hillside backdrop of grapevines etc was stunning to wake up to every morning in a secluded and peaceful place. We enjoyed many mornings having coffee around the poolside deck and afternoons sharing a glass of wine chatting with our friends after our many touring adventures. You definitely need to have a car to enjoy this Villa and surrounding areas like Pisa, Siena, hot Springs, San Gimignano to name a few. Our Caretaker Lia cooked us a delicious Sri Lankan dinner to share on our last night which we enjoyed immensely. Thankyou for hosting us in your home, we didn’t want to leave.

We come from Hong Kong, and a building like this is not often seen there. We are very happy to have had the chance to stay at the house. Some of the details in the house really impressed us, especially the antique furniture! Pietro is a great host—very friendly and responsive. I had some pleasant conversations with him. Thanks again!

This has been the standout accommodation of our Italian tour so far. The photos do not show how amazing this place is. It’s on a vineyard and olive farm with the option for breakfasts (which were fabulous) and we also had a shred meal with others at the accommodation on one night. The food was wonderful and the atmosphere set to be relaxed with several courses taken over a few hours and flowing local wines. The apartment was beautiful and spacious with a very comfortable bed room. We ate in on a few nights and the kitchen was well equipped for making food. Anna was exceptional as a host always very helpful and with such a cheerful positivity. We chose to be away from the main towns to have a peaceful recharge and this accommodation gave us exactly that. Take a walk through the vineyards and capture a sunset that will be etched into your memories. Thanks again Anna for a wonderful stay ❤️

Anna Rita's place was even more beautiful than the pictures and in a great location. Anna Rita's sister, Lucia met us when we arrived. She gave us a tour, explaining how everything works. The space was large and welcoming. The outside terrace was especially beautiful and a peaceful place to unwind. The upstairs master suite was extraordinary. It was comfortable, quiet, spacious and had a balcony overlooking the terrace. The only downside was that the downstairs bedroom could get quite loud due to the adjacent restaurant on the other side of the wall. Our host was always very responsive. We will definitely return!

Giada's penthouse apartment was the perfect spot for a relaxing stay in Tuscany. Accessible to so many Chianti vineyards, we only wish we'd had more time staying there to explore, and less rainy weather, to enjoy the on site amenities like the pool and the two balconies more. She also gave us recommendations for the area which were super helpful! We would happily stay again.

The perfect place to explore Chianti each day. We stayed 5 nights and it was just perfect. Great amenities, beautiful pool, bbqs and lovely areas to sit and enjoy the views and the sunset. Always fabulous to come home to. Our upstairs apartment was spacious, comfortable and all we required with a lovely view. We had great recommendations from Silvia which we followed up on. Great to have restaurants nearby. Reasonable- highly recommend.

What a wonderful place! It’s hard to say whether the interior or exterior is more beautiful, both are absolutely stunning. The house is perfectly decorated and spotlessly clean. We enjoyed postcard-worthy views of Tuscany from the garden and loved the romantic design of the rooms. Our vacation was both fun and relaxing, thanks in large part to Giovanni, Emanuela’s son, who warmly welcomed us and assisted with everything we needed, including reserving a dinner table for us each night. Upon arrival, we were greeted with a thoughtful selection of treats such as milk, eggs, juice, beer, bread, local olive oil, Chianty Reserve wine, coffee, water etc. We even received homemade Italian cookies for Mother’s Day, a kind gesture from Giovanni that made us feel truly welcome. Usually, we stop at a market before check-in, but here we didn’t need a thing. They truly thought of everything. This place sets the bar high! Don’t miss dinner at Tricco, just a 3-minute drive away in the historic center.

We came back to Michele’s place after having visited for 2 weeks in 2019. My dream was to return one day and find our home away from home once again. So here in May 2025 we were able to return to Nicoletta’s beautiful garden full of roses and herbs. The pool is definitely a bonus. Michele takes such care of this home….you can see how much love and commitment he has for this place. There are nearby villages such as Barbarino Val D’elsa and Tignano a short drive away. as well as San Gimignano and Siena, 30 minutes away. A wonderful experience, every time!

We spent 4 nights at Francesco’s farmhouse and loved every minute. The upstairs apartment is spacious with high ceilings and a great space to relax. There was a basket of toys for the kids to enjoy and Francesco kindly provided some of the amazing wines and olive oil from the farm. The location of the farmhouse is absolutely stunning, with incredible views of the surrounding Tuscan countryside. The pool is beautiful and the perfect place to relax and enjoy the view while the kids loved meeting the dog and cats. The location is perfect and an hours drive to most attractions in Tuscany. We went on a number of day trips during our stay including Florence, Cinque Terre & Pisa, as well as smaller villages like San Miniato & Palaia itself. Francesco is a fantastic host and I’m sure we’ll be back one day!

Cristina is a lovely host and the place is beautiful. I’d highly recommend the breakfast that Cristina makes completely fresh!! The swimming pool is immaculate and the whole atmosphere of the place is just lovely. We spent 5 nights here with 2 children (17 and 13) and will definitely return if we ever stay in Tuscany again. Thanks Cristina!

We will definitely be back! The location is about 30-40 minutes from the main city in Florence. Federico recommended we rent a car but we didn’t want to drive in an area we were unfamiliar with. We were provided with the bus schedule which was very easy to take to the city. We planned ahead and bought some groceries in Florence before heading back to the property. We got lucky with getting taxis at the property to eat at a nearby restaurant (Ristorante San Martino) but it wasn’t as convenient as getting one in Florence (had to wait a bit). The place was just as described, very relaxing and just what we wanted! All in all a great experience. We were so sad to leave!

Wow! A real retreat nestled in the Tuscan hills. It’s a short drive from everything you need, but well clear of any commotion. The house has everything you could desire for an enjoyable stay. Best to hire a car as taxi services come far and few between. Charly and Ann were very helpful and will facilitate you well. Thanks guys!