Family-friendly vacation rentals in Certaldo

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 loved this place so much!! We got to pick some fresh vegetables and cook our own dinner and take in the views of the beautiful mountains. Our host was so friendly and helpful. Can’t wait to go back in October!!

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 ❤️❤️❤️

Alessandra received us very hospitably. Everything was well taken care of and clean. The view is amazing and you can walk around anywhere in the beautiful well-kept garden. Wonderful place to relax and unwind. We bought a delicious bottle of olive oil from our own olive garden. Supermarket is easy to reach by car in terms of distance. You can use the washing machine. I recommend visiting Tuscany!

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

We had a wonderful week in Gloria's house. Our four-legged friend also felt totally comfortable in nature. The house is small but nice and has everything you need. The property is a nice size and is perfect for eating outside, relaxing in the hot tub or just lying in the sun. The way to the house is a little challenging, but with a normal car and a little driving experience it can be mastered. Gloria was always available to us and gave us good excursion tips for the area in advance. Even with any inquiries, she always responded very quickly and helped us. To just get out and enjoy the nature and tranquility of Tuscany, it is perfect. We will be happy to come back!

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.

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 my favorite Air BnB host of all time. This is a lovely Tuscan home which is exactly what we wanted. The home had all the old farmhouse touches. Beatrice went out of her way to be helpful and provide lots of great information about the area. We did everything she suggested and had a great time in the area. Will definitely be back. thank you B.

Gemma, our hostess, kindly welcomed us on the street despite our late arrival. She had kindly prepared a bottle of wine on the table, cold drinks in the fridge, and cookies for breakfast and her dad's oil. She showed us her nice apartment, the patio and explained how selective sorting works. The impression of living the Italian way in a small town well located for visiting the San Gimignano region (which can be seen in the distance from the patio) and Siena

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!

We loved staying at Helga and Federico’s apartment! The place was very clean and nearby one of the main gates, with many restaurants, parking options, and things to do. Federico gave us recommendations for places to go, and it is clear he loves this town!

What a really fantastic stay at Anna's place!!! She and her husband have created a little paradise next to their house, behind a small chapel on the pilgrim path on a beautiful green hill! It is wonderfully private and quiet, while all the sights of Tuscany are close by. Furthermore, there is also a lot to discover in the very nearby area. You can retreat there wonderfully; away from all the tourists at the hotspots. Sooo nice!! This place just has very good vibes, as far as we are concerned! So, if you like to be some on your own and looking for peace, authenticity and no shared outdoor space with other tourists, then I can only say: 100% recommended!!!! We felt completely at home there and made very nice memories during our vacation. We will definitely come back!

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.

The wonderful view can be enjoyed both as a couple and with friends. It is very quiet and everything has been thought of: outside there are very comfortable seating options, a grill and pool. The garden smells of jasmine everywhere. There's nothing missing inside either. The house is perfect and is in the perfect location. After 20 minutes by car you can reach San Gimignano. Simply a dream and always worth a trip 😍

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!

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.

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!