Some info is shown in its original language. Translate

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 stars5 days ago
Unser Aufenthalt war ein Traum. Francesca und Francesco haben einen wunderbaren Ort geschaffen, sind sympathische Menschen und tolle Gastgeber. Wir wurden herzlich begrüßt und haben alle nötigen Informationen erhalten. Vom ersten Moment an haben wir uns zuhause gefühlt und konnten das liebevoll gestaltete Gelände frei erkunden und auch in Privatheit genießen. Auch der Kontakt zu anderen Gästen war angenehm und respektvoll. Die Räume sind rustikal und geschmackvoll eingerichtet und versprühen einen besonderen Charme. Der Ausblick ist atemberaubend. Die Anfahrt zur Poderracio ist entsprechend abenteuerlich (Serpentinen und enge, holprigen Straße). Alle Produkte wie z.B. der Frühstückskorb sind super lecker und von hoher Qualität . Zusätzlich haben wir von Francesca frisch geerntetes Gemüse (Zucchinis, rote Beete, Zwiebeln und Knoblauch) bekommen. Während des Aufenthalts wurden wir zum gemeinsamen Pizzabacken in den Privaträumen eingeladen und genossen einen wunderschönen Abend. DANKE!
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

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
4.83 out of 5 average rating, 120 reviews

I Limoni Apartment in Tuscany

PamelaRating, 5 stars2 weeks 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 favorite
Home in Figline e Incisa Valdarno
4.96 out of 5 average rating, 105 reviews

Torretta Apartment

DebbieRating, 5 stars2 weeks 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 stars3 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

Splendido fienile ristrutturato in Toscana

PhilippRating, 5 stars1 month ago
Wir hatten eine wunderschöne Woche in Glorias Haus. Unser vierbeiniger Freund hat sich in der Natur auch total wohl gefühlt. Das Haus ist klein aber fein und hat alles was man braucht. Das Grundstück hat eine schöne Größe und eignet sich perfekt um draußen zu Essen, im Whirlpool zu entspannen oder einfach in der Sonne zu liegen. Der Weg zum Haus ist ein wenig anspruchsvoll, aber mit einem normalen Auto und ein bisschen Fahrpraxis durchaus zu meistern. Gloria war für uns immer erreichbar und hat uns bereits im Vorfeld gute Ausflugstipps für die Gegend gegeben. Auch bei eventuellen Nachfragen hat sie immer sehr schnell reagiert und uns geholfen. Um einfach mal raus zu kommen und die Natur und die Ruhe der Toskana zu genießen, ist es perfekt. Wir kommen gerne wieder!
Guest favorite
Villa in San Casciano In Val di Pesa
4.94 out of 5 average rating, 173 reviews

Wheelchair accessible Villa with Jacuzzi

AleksandarRating, 5 stars1 week ago
We had a really good time at this place. It was spacious, clean, and worked perfectly for our group. There were plenty of bathrooms, and the house had all the amenities you might need for a comfortable stay. The outdoor space was a big plus—especially the terrace and patio area with the big table, which was great for hanging out and having meals together. The location is honestly perfect—super peaceful, but just a short drive to Florence, great local restaurants, and vineyards. Also, there was tons of parking space, which made things super easy for us. Check-in was smooth and the host was really helpful. Would definitely stay here again.
Guest favorite
Condo in Casole d'Elsa
4.93 out of 5 average rating, 157 reviews

La Casetta

RalfRating, 5 stars3 weeks ago
Können wir absolut empfehlen ! Ist alles so wie im Text beschrieben und auf den Foto´s zu sehen. Liegt ca 2 km außerhalb vom total schnuckeligen Örtchen Casole de Elsa. Von Andrea + Barbara gab´s alle nötigen Infos zur Anreise und viele tolle Tipps vor Ort, immer mit den dazugehörigen Links. Zum Beispiel verzögerte sich unsere Anreise verkehrsbedingt auf ca. 22:15 Uhr. War kein Problem, wir standen in Kontakt und als wir ankamen, hat uns Andrea persönlich in Empfang genommen. Und wenn wir während unseres Aufenthaltes eine Frage hatten, kam immer sehr zügig eine Antwort. (Wo man in Siena am Besten parken kann, wie gelangt man am Besten nach Florenz, ...)

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
Farm stay in Siena
4.97 out of 5 average rating, 275 reviews

Authentic Tuscan Country House WITH A/C

JamesRating, 5 stars1 week 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.
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
Nous avons été de suite sous le charme de cette propriété. Tout ici compose l'image qu'on peut se faire de la belle campagne Toscane. Tout en haut de la colline surplombant la vallée, la vue y est splendide et romantique. La propriété a été renovée avec le confort d'aujourd'hui tout en conservant son âme d'autrefois. On s'y sent de suite bien, l'energie est bienfaisante, la nature, les animaux, tout est en harmonie! L'accueil, la cuisine d'Oscar, la superbe piscine, la terrasse ombragée, les petits-dejeuners copieux fait maison! C'est plus qu'un coup de coeur, cet endroit est une pépite! Nous reviendrons!
Top guest favorite
Home in San Gimignano
4.95 out of 5 average rating, 224 reviews

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

ViolaineRating, 5 stars3 weeks ago
Béatrice est la meilleure hôtesse Airbnb avec qui nous ayons eu l’occasion de faire affaire à ce jour. En plus de sont EXTRÈME générosité tant au niveau de ses recommandations, de ses explications et du soucis de notre bien-être, le logement était exactement ce que nous recherchions pour vivre notre expérience toscane. Il est très bien situé, à distance de marche de San Giminiamo à travers les vignobles et le décor enchanteur. Être chez les ancêtres de Béatrice a aussi contribué à nous faire vivre une expérience unique. Le lieu rempli de d’objets antiques nous a plongé dans une vie toscane rythmée par l’agriculture et la culture du pays. Le lieu invitait réellement à la détente: parfait pour y vivre le scénario rêvé sous Le Soleil de la Toscane. Mon rêve serait d’y retourner un jour avec mes parents pour avoir la chance de partager ce bijou de lieu.
Guest favorite
Castle in Barberino Tavarnelle
4.88 out of 5 average rating, 112 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!
Top guest favorite
Villa in Certaldo
4.89 out of 5 average rating, 148 reviews

Tuscan farmhouse with private pool and views

MelissaRating, 5 stars1 week 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
Guest favorite
Farm stay in San Casciano In Val di Pesa
4.94 out of 5 average rating, 104 reviews

Paradiso nel Chianti

JillRating, 5 stars4 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

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

Esplora la natura al centro di Vigneti Chianti

BaileyRating, 5 stars2 weeks 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
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 😍
Top guest favorite
Vacation home in Panzano
4.97 out of 5 average rating, 150 reviews

Fienile Santa Teresa

AndreasRating, 5 stars1 week ago
Traumhaft und ruhig gelegene Unterkunft im Herzen des Chianti Gebietes mit fantastischem Ausblick . Ein Auto ist unbedingt notwendig! Das Haus, der Garten sowie der großzügige Pool waren genial. Toskana Feeling pur. Christine und John waren großartige Gastgeber. Christine hatte tolle Restaurant Tipps und hat sogar die Reservierungen für uns vorgenommen (Somit waren auch immer gute Sitzplätze in den Restaurants garantiert). Wir waren einen Tag sogar in Ihrer anderen Unterkunft der „Villa La Petraia“ zu Gast. Die Zimmer waren sehr liebevoll eingerichtet und das Anwesen und der Ausblick auch traumhaft. Christine hat ein ausgesprochen gutes Gespür für Design und Einrichtung. Ein Design Hotel vom Feinsten. Ich hoffe bald wieder zu kommen.
Superhost
Apartment in Larciano
4.84 out of 5 average rating, 123 reviews

Biancospino apart, amazing view, pool open fromApr

SylviaRating, 5 stars1 month ago
Top locatie, met prima voorzieningen. Het uitzicht is prachtig en een dikke plus voor de privé kookles! Niet twijfelen, gewoon boeken.
Top guest favorite
Hut in Poggibonsi
4.94 out of 5 average rating, 131 reviews

Lovely barn with pool between Siena and Florence

MarilynRating, 5 stars3 weeks ago
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!
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.
Guest favorite
Farm stay in San Casciano In Val di Pesa
4.78 out of 5 average rating, 154 reviews

Sperone: two floors apartment with pool

JoséRating, 5 stars2 weeks ago
Fantastische accommodatie op prachtig landgoed van wijnhuis Villa Le Corti. Rondleiding gehad door wijnhuis en olijfolie productie. Veel privacy en schitterend zwembad. Bijzondere groentetuin waar gebruik gemaakt wordt van Elettro Coltura Op 25 minuten rijden van Florence. Op eigen terrein een Osteria waar je geweldig kan lunchen en dineren met veel wijn en heerlijke olijfolie.

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

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$10,454 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