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Family-friendly holiday rentals in Certaldo

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Certaldo family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Farm stay in Figline e Incisa Valdarno
4.93 out of 5 average rating, 323 reviews

Bioagriturismo colline Firenze 3p

AnoukRating, 5 stars2 weeks ago
Heerlijk verbleven met onze dochter van 1 jaar. Er was een badje en een kinderstoel aanwezig. Wel moet je de auto in wil je ergens komen, het is een best lastig weggetje voor de eerste keer. Genoten van de rust en de ruimte!
Guest favourite
Condo in Montevarchi
4.95 out of 5 average rating, 192 reviews

Art-Design Fienile in the heart of Tuscany

AlisterRating, 5 stars1 week ago
Incredible trip. Paola and Michele were so friendly and welcoming. Always there to give advice and make sure you had everything you needed. The little converted hay barn was just beautiful and lovely. Location wise it just couldn’t be beaten. The garden was amazing and we ate outside morning and night, easy access to amazing Tuscany countryside and also a short trip on the train to Florence from Montevarchi. Loved every minute we were there and we were sorry to leave. Would highly recommend.
Top Guest favourite
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

SandraRating, 5 stars1 week ago
Massimo beschreibt den Weg zur Unterkunft sehr gut, das Häuschen liegt etwa 20 min südlich von Florenz mitten in den Weinbergen, sehr ruhig und malerisch in den toskanischen Hügeln. Wir waren zu dritt bei Massimo und uns hat es an nichts gefehlt! Ob Stadtbesichtigung von Siena& Florenz, Weinverkostung oder einfach die Ruhe am Haus genießen: für alles das perfekt geeignet! Das Haus ist typisch toskanisch, Massimo und Beatrice haben viel Arbeit reingesteckt um ihren Gästen einen authentischen Aufenthalt zu bieten: trotzdem aber modern mit Klimaanlage- im Sommer geht’s auch kaum ohne! Vielen Dank für die tolle Zeit!
Superhost
Home in Montespertoli
4.84 out of 5 average rating, 119 reviews

I Limoni Apartment in Tuscany

PamelaRating, 5 stars1 week ago
Excelente estadía, ¡superó mis expectativas! Tuvimos una maravillosa experiencia durante nuestra estancia. El alojamiento estaba impecablemente limpio, bien equipado y se veía tal como en las fotos. La cama era muy cómoda y el lunar tranquilo, ideal para descansar. La ubicación fue perfecta! Los anfitriones fueron muy amables y atentos, siempre disponible para responder cualquier duda y brindar recomendaciones locales. La comunicación fue fluida desde el primer momento. Sin duda volvería a hospedarme aquí. ¡Altamente recomendado para quienes buscan comodidad, limpieza y una atención excelente!
Top Guest favourite
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 favourite
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 favourite
Villa in San Casciano In Val di Pesa
4.94 out of 5 average rating, 170 reviews

Wheelchair accessible Villa with Jacuzzi

GaryRating, 5 stars1 month ago
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.
Top Guest favourite
Cottage in Geggiano
4.99 out of 5 average rating, 133 reviews

Villa di Geggiano - Guesthouse

CharlesRating, 5 stars2 weeks ago
Everything about this place was magical and refined and peaceful. It was like stepping out of time and into a space of beauty and peace. Birds singing, frogs chirping, fire flies lighting up the night. Andrea was so friendly and so helpful and so generous. I definitely want to come back and stay longer. I can even imagine my daughter’s wedding there. We look forward to our next opportunity to stay!

Family- and pet-friendly home rentals

Guest favourite
Townhouse in Scandicci
4.87 out of 5 average rating, 290 reviews

Florence Country Side: Giogoli a place to be!

DonnyRating, 5 stars2 days ago
The pictures don’t do the beauty of the space justice. Maria, the housekeeper who lives in the basement unit was very discrete. Dawn was our host and set us up some incredible reservations, as well as helped us with a transportation issue. The view is otherworldly off the back porch, which overlooks olive trees. There are many adorable tortoises that live in the backyard and are very fun to watch. Close drive from the tram as well as many incredible restaurants. Take the cooking class with Maria!!! It was a trip highlight. If you stay here, you will definitely want a car.
Top Guest favourite
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 favourite
Condo in San Gimignano
4.95 out of 5 average rating, 130 reviews

Adalberto Apartment inside the Manor of Fulignano

KevinRating, 5 stars4 weeks 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 favourite
Farm stay in Siena
4.97 out of 5 average rating, 275 reviews

Authentic Tuscan Country House WITH A/C

JamesRating, 5 stars6 days ago
The apartment was exactly as advertised. In fact, not sure the pictures do it justice. It is a beautiful setting - peaceful and relaxing. The space in the apartment was very usable with two bathrooms and a nice kitchen. Martina was super helpful and communicated well with fast response time. Great recommendations for walks and restaurants. I can’t say enough nice things about her. Just an ideal host.
Top Guest favourite
Apartment in Tavarnelle
4.93 out of 5 average rating, 136 reviews

Appartamento nel Chianti

AtulRating, 5 stars2 weeks ago
We had a great experience. The host provided very good instructions and tips for arrival and even waited for us outside to welcome us. The apartment is very nice with all the amenities. A bottle of wine as a welcome gift was a nice touch. Hosts helped us with any questions we had during our stay. The Patio downstair is really nice with amazing views. We enjoyed our evening drinks sitting there and enjoying the nature/view. Hosts gave us recommendations for restaurants at walking distance. We tried a few of them and all turned out really good. Highly recommend.
Top Guest favourite
Apartment in La Presura
4.93 out of 5 average rating, 146 reviews

Country house 9 km to Florence-2+1g,free parking

AndreaRating, 5 stars2 weeks ago
This was such an amazing stay! Very quiet, peaceful, and relaxing stay far away from the major cities. Beautiful views from everywhere! Would recommend doing their wine tour on site. It was fun, informative, and delicious! You definitely will need a car to get to this place in addition to restaurants and grocery stores. Would highly recommend this place!
Guest favourite
Castle in Barberino Tavarnelle
4.87 out of 5 average rating, 111 reviews

Suite in Castello di 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 favourite
Farm stay in San Casciano In Val di Pesa
4.94 out of 5 average rating, 102 reviews

Paradiso nel Chianti

JulieRating, 5 stars3 weeks ago
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 ❤️

Family-friendly home rentals with a pool

Guest favourite
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 192 reviews

Stone House with Exclusive Pool Codilungo in Chianti

SarahRating, 5 stars1 week 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!
Superhost
Villa in Gambassi Terme
4.85 out of 5 average rating, 152 reviews

Il Leccio - Tuscany home near San Gimignano

MilaRating, 5 stars3 weeks ago
Die herrliche Aussicht kann man sowohl als Paar, als auch mit Freund*innen wunderbar genießen. Es ist sehr ruhig und an allem gedacht worden: draußen gibt es sehr bequeme Sitzmöglichkeiten, einen Grill und Pool. Im Garten duftet es überall nach Jasmin. Auch innen fehlt an nichts. Das Haus ist perfekt und befindet sich am perfekten Ort. Nach 20 Minuten Autofahrt erreicht man San Gimignano. Einfach ein Traum und immer wieder eine Reise wert 😍
Superhost
Apartment in Larciano
4.84 out of 5 average rating, 122 reviews

Biancospino apart, amazing view, pool open fromApr

SylviaRating, 5 stars3 weeks ago
Top locatie, met prima voorzieningen. Het uitzicht is prachtig en een dikke plus voor de privé kookles! Niet twijfelen, gewoon boeken.
Top Guest favourite
Farm stay in Palaia
4.98 out of 5 average rating, 169 reviews

Countryside Dream farm in Tuscany

MercedesRating, 5 stars2 days ago
We had the most magical stay at this Tuscany farm! The property is absolutely stunning — nestled among rolling vineyards and olive groves, with postcard-perfect views in every direction. Our apartment was spacious, charming, and had everything we needed for a comfortable stay. The hosts were incredibly kind and welcoming, sharing local recommendations. Our kids loved meeting the animals, exploring the grounds, and especially swimming in the beautiful pool overlooking the hills — it was a total dream! Evenings on the terrace with a glass of wine and the Tuscan sunset were unforgettable. This was a once-in-a-lifetime experience for our family, and we can't wait to return. Highly recommend to anyone looking for a peaceful, authentic Tuscan escape! 🌿🍷☀️
Top Guest favourite
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 stars5 days 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.
Guest favourite
Home in Pievescola
4.94 out of 5 average rating, 175 reviews

Antico Borgo Ripostena – n. 8 Casa Vecchia

LucyRating, 5 stars2 weeks ago
This place is something else! The views, the pool, the houses, the interior - it’s something else. We stayed with our 18 month old and had such a happy time - surrounded by nature in such gorgeous accommodation and a kiddy kitchen / toys which were perfect for Otis. It’s simply beautiful and Martina is so helpful - highly recommend with a family or groups of friends for a zen and unique time. Close to lots of gorgeous places and Martina has wonderful recommendations. Only watch out is the 2km dirt track road to get to the location but it’s 100% worth it and quite fun! Enjoy - we can’t wait to come back :)
Top Guest favourite
Villa in Montespertoli
4.94 out of 5 average rating, 182 reviews

Colonica nel Chianti

DanielleRating, 5 stars3 weeks ago
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.
Top Guest favourite
Villa in Certaldo
4.89 out of 5 average rating, 148 reviews

Tuscan farmhouse with private pool and views

MelissaRating, 5 stars4 days ago
Incredible! We had such an amazing time staying here. Charly & Ann have done it up so beautifully. The views are incredible and it’s so peaceful. They went above and beyond answering any questions and recommended an amazing winery to visit! Would highly recommend a visit to this beautiful home. Thank you Charly & Ann

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

  • Total rentals

    30 properties

  • Nightly prices starting at

    $77 AUD 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

  • Wi-Fi availability

    30 properties include access to Wi-Fi

Destinations to explore