Some info has been automatically translated. Show original language

Family-friendly vacation rentals in Certaldo

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Certaldo family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Farm stay in Figline e Incisa Valdarno
4.92 out of 5 average rating, 325 reviews

Bioagriturismo colline Firenze 3p

JayRating, 5 stars4 days ago
Our stay was a dream to be in. Francesca and Francesco have created a wonderful place, are likeable people and great hosts. We were warmly welcomed and received all the necessary information. From the first moment, we felt at home and could freely explore the lovingly designed grounds and also enjoy them in privacy. The contact with other guests was also pleasant and respectful. The rooms are rustic and tastefully decorated and exude a special charm. The view will take your breath away. The approach to Poderracio is correspondingly adventurous (hairpin bends and narrow, bumpy road). All products such as the breakfast basket are super delicious and of high quality. In addition, we received freshly harvested vegetables (zucchini, beets, onions and garlic) from Francesca. During the stay, we were invited to bake pizza together in the private rooms and enjoyed a wonderful evening. THANKS!
Top guest favorite
Cottage in San Casciano In Val di Pesa
4.95 out of 5 average rating, 147 reviews

Il Fienile, Cottage in the country with Jacuzzi

BethanyRating, 5 stars3 weeks ago
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.
Superhost
Home in Montespertoli
4.83 out of 5 average rating, 120 reviews

I Limoni Apartment in Tuscany

WiktoriaRating, 5 stars1 month ago
Incredible home, with stunning views! I hosted a group of friends here before my wedding, and we all agreed it was the most beautiful Airbnb we have ever stayed in. The hosts (Francesco and his wife Illaria) were extremely responsive and kind. They recommended a local chef to us, which turned into one of the best nights of our trip. 100% recommend and will be re-booking next time I travel to Tuscany.
Top guest favorite
Home in Figline e Incisa Valdarno
4.96 out of 5 average rating, 105 reviews

Torretta Apartment

DebbieRating, 5 stars1 week ago
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!
Guest favorite
Villa in Monteroni d'Arbia
4.98 out of 5 average rating, 102 reviews

San Giovanni in Poggio, villa Meriggio 95mq

CraigRating, 5 stars2 weeks ago
Authentic Tuscan countryside experience, with amazing views and excellent facilities. Well located if you want to explore all that Tuscany has to offer.
Guest favorite
Cottage in Radicondoli
4.93 out of 5 average rating, 137 reviews

Beautiful renovated barn in Tuscany

PhilippRating, 5 stars4 weeks ago
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!
Guest favorite
Villa in San Casciano In Val di Pesa
4.94 out of 5 average rating, 171 reviews

Wheelchair accessible Villa with Jacuzzi

KristinRating, 5 stars1 week ago
This was such a beautiful stay in Tuscany. When our family arrived it was magical to them to be in Beatrice’s home and countryside. It’s full of history and breathtaking views.
Guest favorite
Condo in Casole d'Elsa
4.93 out of 5 average rating, 157 reviews

La Casetta

RalfRating, 5 stars3 weeks ago
We can absolutely recommend it! Everything is as described in the text and seen in the photos. Located about 2 km outside the totally cute village of Casole de Elsa. Andrea + Barbara provided all the necessary information about the arrival and many great local tips, always with the corresponding links. For example, our arrival was delayed due to traffic to about 10:15 pm. Was no problem, we were in contact and when we arrived, Andrea personally welcomed us. And if we had a question during our stay, an answer always came very quickly. (Where to park in Siena, how to get to Florence, ...)

Family- and pet-friendly home rentals

Top guest favorite
Villa in San Casciano
4.97 out of 5 average rating, 110 reviews

Luxury Villa in the very heart of Chianti

MelissaRating, 5 stars1 month ago
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!
Guest favorite
Condo in San Gimignano
4.95 out of 5 average rating, 130 reviews

Adalberto Apartment inside the Manor of Fulignano

KevinRating, 5 stars1 month ago
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.
Top guest favorite
Home in Tavarnelle Val di Pesa
4.96 out of 5 average rating, 296 reviews

Casa Al Poggio & Chianti view

KathyRating, 5 stars3 weeks ago
Hands down our favorite part of our two weeks in Italy! Casa Al Poggio was our Tuscan home away from home. We went and did all the things… Florence, Cinque Terre, San Gimignano, Montepulciano, etc. But coming “home” to this place was the best. So peaceful and picturesque looking across the valley at the Badia Di Passignano. We cooked many meals in the well stocked kitchen and my husband loved the rustic BBQ. Fresh herbs in the garden and the smell of jasmine blooming on the patio. Book yourself extra time here…you won’t want to leave! Emanuele & Tamara are the kindest people. Take them up on all of their restaurant recommendations. Everyone one was a hit! We can’t wait to go back.
Superhost
Condo in Castelfranco di Sopra
4.83 out of 5 average rating, 252 reviews

House between Firenze, Arezzo, chianti e Siena

Sylvie & AlainRating, 5 stars1 week ago
We immediately fell in love with this property. Everything here makes up the image that can be made of the beautiful Tuscan countryside. At the top of the hill overlooking the valley, the view is splendid and romantic. The property has been renovated with today's comforts while retaining its soul of yesteryear. You feel good there, the energy is beneficial, nature, animals, everything is in harmony! The welcome, Oscar's cooking, the superb swimming pool, the shaded terrace, the hearty homemade breakfasts! It's more than a favorite, this place is a gem! We'll be back!
Top guest favorite
Home in San Gimignano
4.95 out of 5 average rating, 224 reviews

Tuscan family house:green, relax "towers view!"

Mafalda E SalvadorRating, 5 stars1 month ago
Thank you very much for your kindness and for the fantastic family home. Beatrice's recommendations were fantastic (we followed all her recommendations for both San Gimigniano and Piza and Siena) and we felt right at home.
Top guest favorite
Farm stay in Siena
4.98 out of 5 average rating, 262 reviews

Typical Tuscan Country House WITH A/C

KathrynRating, 5 stars3 weeks ago
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.
Guest favorite
Castle in Barberino Tavarnelle
4.87 out of 5 average rating, 111 reviews

Suite in Castle of Valle

KapoRating, 5 stars3 weeks ago
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!
Guest favorite
Farm stay in San Casciano In Val di Pesa
4.94 out of 5 average rating, 103 reviews

Paradise in Chianti

JillRating, 5 stars3 days ago
What a magnificent place to stay. Very peaceful and in wonderful surroundings. The dinner that Anna put on was amazing and we met some lovely fellow travellers. As the temperature was hot while we were there the pool was an added bonus. I would highly recommend this place. Anna is such a delight to deal with.

Family-friendly home rentals with a pool

Top guest favorite
Vacation home in San Donato In Poggio
4.98 out of 5 average rating, 140 reviews

Chianti Penthouse with panoramic View & Pool

AntoniaRating, 5 stars1 month ago
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.
Guest favorite
Cottage in Barberino Tavarnelle
4.97 out of 5 average rating, 193 reviews

Stone House with Exclusive Pool Codilungo in Chianti

SarahRating, 5 stars2 weeks ago
We can't imagine a more beautiful place to stay while we visited Chianti! The location is absolutely heavenly, and Emanuela's home is stunning. Everything was so comfortable, and our family particularly loved spending time outside and enjoying the pool. It's conveniently located for several Tuscan day trips, and there are many amazing wineries nearby. And the icing on the cake were Emanuela and Giovanni, who went above and beyond in helping us throughout our trip - from recommendations and help with reservations to having a few food items and coffee stocked for our first day's breakfast. Easily the best hosts we've ever enjoyed in our years staying in Airbnbs!
Top guest favorite
Farm stay in Arezzo
4.97 out of 5 average rating, 230 reviews

Explore nature in the center of Vigneti Chianti

BaileyRating, 5 stars1 week ago
Staying at Agrigreen La Lama was hands down the best Airbnb experience I’ve ever had. From the moment we arrived, Rita welcomed us with such warmth and hospitality that we felt at home. The property is peaceful, beautifully maintained, and full of charm—surrounded by nature and the kind of quiet that soothes the soul. One of the most memorable parts of our stay was getting to cook in Rita’s own home, which she generously opened to us. It was such a unique and personal experience that made us feel truly connected to the space and the spirit of the farm. If you’re looking for a place to slow down, feel grounded, and enjoy genuine hospitality, Rita’s space is an absolute gem. I’m already looking forward to the day I can return.
Superhost
Villa in Gambassi Terme
4.85 out of 5 average rating, 152 reviews

Il Leccio - Tuscany home near San Gimignano

MilaRating, 5 stars4 weeks ago
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 😍
Top guest favorite
Vacation home in Panzano
4.97 out of 5 average rating, 150 reviews

Fienile Santa Teresa

ZoeRating, 5 stars4 days ago
Christine and John were the best hosts, making this incredible location even more enjoyable. They went above and beyond, recommending restaurants, wineries and experiences that made our trip unforgettable. Christine also helped us get our lost luggage back, ringing the airport for us and liaising with a driver in Florence to pick it up and drop it off to us. Incredible service. Absolutely recommend!
Top guest favorite
Farm stay in Lastra a Signa
4.99 out of 5 average rating, 145 reviews

Flat for 4 with garden & pool in agriturismo

MollyRating, 5 stars1 week ago
What a magical stay! Christine is a true host and not only has curated a beautiful space but she also was perfectly attentive to us during our stay. The apartment was as comfortable as it is beautiful. We took advantage of the outdoor grill and swimming pool and although we explored the area we would have been just as happy to stay “home” all day. The recommendations for the area were true gems. We had breakfast our last morning and it was the perfect ending to our stay! I don’t think you can find a more perfect place.
Top guest favorite
Farm stay in Pian di Scò
4.95 out of 5 average rating, 132 reviews

Agriturismo I Gelsi

GabriellaRating, 5 stars1 week ago
Eva's place is absolute heaven. We stayed for 10 days with our two small children (1 and 4) and had the most wonderful time. The apartment is perfect – beautifully decorated with everything catered for. The outside garden and terrace is great for eating with amazing views. And the pool is also wonderful – we had it to ourselves the whole time we were there. We couldn't recommend this place more! Thank you, Eva and family!
Guest favorite
Farm stay in San Casciano In Val di Pesa
4.78 out of 5 average rating, 153 reviews

Sperone: two floors apartment with pool

MatthewRating, 5 stars3 weeks ago
Amazing villa and location. Amenities were beautiful and restaurant was amazing. Plenty of parking and access. Great back yard and swimming pool for kids with amazing views.

Quick stats about vacation rentals that are family-friendly in Certaldo

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$10,460 GYD before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

Destinations to explore