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Family-friendly holiday rentals in Siena

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Siena 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, 324 reviews

Bioagriturismo colline Firenze 3p

JayRating, 5 stars2 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 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!
Guest favourite
Apartment in Montevarchi
4.95 out of 5 average rating, 192 reviews

Art-Design Fienile in the heart of Tuscany

AlisterRating, 5 stars2 weeks 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.
Guest favourite
Cottage in Radicondoli
4.93 out of 5 average rating, 137 reviews

Splendido fienile ristrutturato in Toscana

PhilippRating, 5 stars4 weeks 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!
Top guest favourite
Flat in Siena
4.91 out of 5 average rating, 129 reviews

Villa’Colombaiolo di Marciano',28

EwaRating, 5 stars2 weeks ago
Wygodny choć nieco staromodny apartament w spokojnej okolicy, wokół dużo zieleni i piękny widok z okna. Duży i zadbany basen z przestrzenią do odpoczynku. Dobre miejsce na relaks po zwiedzaniu Sieny i okolic.
Guest favourite
Apartment 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, ...)
Guest favourite
Villa in Chianciano Terme
4.92 out of 5 average rating, 107 reviews

Cottage in Val d'Orcia, Jacuzzi & HotTub with view

MadisonRating, 5 stars1 week ago
Fulvia’s apartment is a true Tuscan gem—beautifully decorated with charm and character, and equipped with everything you need. The property offers stunning views and a peaceful sense of seclusion, and it’s even more beautiful than in the photos. Fulvia is right nearby and always available if you need anything. She and her husband are both warm, thoughtful, and made us feel genuinely welcome. Fulvia even arranged dinner at a local restaurant, which turned out to be one of the best meals of our trip. This is a special place and our only regret is not staying longer.
Top guest favourite
Home in Siena
4.96 out of 5 average rating, 134 reviews

Domus Nannini - Loggia Salimbeni SPA

YingRating, 5 stars1 month ago
这是住过最好的最有特色的民宿,像宫殿一样的房间,四面墙加顶都是湿壁画,叹为观止,设施也非常齐全,最最关键是房东态度很好,入住时帮我们提东西,入住后一直在关心我们,给我们准备了很多水和零食,问候入住的体验感,告诉我们哪里吃东西比较方便也推荐了很多当地比较好的餐厅。强烈推荐!

Family- and pet-friendly home rentals

Guest favourite
Home in Cortona
4.94 out of 5 average rating, 202 reviews

Casa del Passerino

MadsRating, 5 stars1 week ago
Hyggelig rummelig lejlighed så centralt som overhovedet muligt. Alt fungerer fint. God seng men ingen gode møbler at sidde, desværre. Men det er også det eneste minus.
Top guest favourite
Castle in Montecatini Val di Cecina
4.99 out of 5 average rating, 117 reviews

Torre dei Belforti

CharlieRating, 5 stars1 week ago
This was an incredible and relaxing getaway—we honestly wish we had stayed longer. The tower is just as magical as the photos, and the views, olive grove, and pool were even better than expected. The surrounding town is darling and quiet, with just a couple of small restaurants and markets, which made it feel like a true escape. Luca was kind and responsive throughout our stay. Just a few things to note: there are a lot of stairs, and you’ll want a smaller car to navigate the narrow roads leading up to the tower. It’s a real castle, so it’s older and rustic—but full of charm and clearly loved. The only downside was that the hot tub on the roof no longer works, which was a bit of a letdown. Still, we absolutely loved our time here and would highly recommend it.
Top guest favourite
Farm stay in Arezzo
4.97 out of 5 average rating, 230 reviews

Esplora la natura al centro di 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.
Top guest favourite
Flat in Laviano
4.95 out of 5 average rating, 141 reviews

Farmhouse with swimming pool with wonderful view

KristinaRating, 5 stars1 week ago
We loved our stay so much we extended for another two nights! The area is very private so make sure you have a rental car and purchase groceries. Lots of cute towns close by but nothing within walking distance. The pool was great and we almost had the place to ourselves. The second two days had more guests around which was nice as well. The hosts were lovely and friendly and available for any questions. Great spot!
Top guest favourite
Flat in La Presura
4.93 out of 5 average rating, 147 reviews

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

TimRating, 5 stars6 days ago
Sehr schöne ruhige Unterkunft im toskanischen Flair. Tolle Anlage auch mit Pool und toller Aussicht. Schnell in Florenz und auf den Straßen zu den Ausflugszielen. Auf jeden Fall zu empfehlen! Wir kommen gern wieder. :)
Superhost
Farm stay in Roccatederighi
4.92 out of 5 average rating, 136 reviews

Holiday in antique farm, Belvedere

MauriceRating, 5 stars2 weeks ago
Wat een rust en wat een uitzicht. Mooi landgoed en supervriendelijk mensen die het je naar de zin proberen te maken. Ook een mooi en fijn zwembad voor als het erg warm is.
Top guest favourite
Apartment in Monteriggioni
4.92 out of 5 average rating, 122 reviews

Il Vecchio Noce

JuliaRating, 5 stars3 weeks ago
Eine super schöne Unterkunft. Der Weg dorthin ist ein bisschen abenteuerlich und nicht für tiefer gelegte Fahrzeuge zu empfehlen, aber sonst gut machbar wenn man langsam fährt. Dafür ist es aber auch total ruhig dort. Das Häuschen ist niedlich eingerichtet. Alles wichtige war vorhanden und Alessandro hat uns sogar mit einer Flasche Wein begrüßt. Das Bett und die Kissen sind ausgesprochen bequem. Etwas störend ist die fiepende Gastherme und die Tatsache, dass die Wassertemperatur in der Dusche ziemlich geschwankt hat. Vielleicht lässt sich das ja noch reparieren. Aber das ist schon jammern auf hohem Niveau. Alles in allem eine tolle Unterkunft mit einem sehr netten und zuvorkommenden Gastgeber.
Top guest favourite
Flat in Montepulciano
4.97 out of 5 average rating, 392 reviews

A view from the top, Montepulciano

AliciaRating, 5 stars4 weeks ago
We had a wonderful stay at Luca’s and the view cannot be beat! Luca went above expectations by meeting us at checkin to show us where to park and taking our luggage to and from the unit. Hope to stay here again one day!

Family-friendly home rentals with a pool

Top guest favourite
Farm stay in Pisa
4.99 out of 5 average rating, 298 reviews

Tenuta Chiudendone in Tuscany

KarenRating, 5 stars5 days ago
Wonderful place for a family and to recharge in our busy trip to Italy. Sign up for the farm to table experience when you stay. The hosts could not have been more helpful and wonderful. Beautiful property and accommodation.
Top guest favourite
Villa in Tavarnelle Val di Pesa
4.94 out of 5 average rating, 147 reviews

PODERE GUIDI

TerryRating, 5 stars1 week ago
Giuliani is a wonderful host who made us feel as if this slice of paradise was our home, too. The location, the meticulously restored home, the views all make for the ultimate Tuscan experience. But Giuliani and her husband bring it all together with their warmth and attentiveness. It was a tough place to say goodbye to — for now. If you are looking for a Tuscan experience, this is it. And remember to ask for the hosts’ home-cooked meal. It is a culinary experience in the very best sense.
Guest favourite
Farm stay in Cavriglia
4.92 out of 5 average rating, 336 reviews

Chianti La Pruneta, Raffaello Apartment

KathleenRating, 5 stars1 week ago
Very friendly and helpful host, Massimo made us feel at home. A beautiful apartment overlooking some incredible views. Lovely clean pool. Just a perfect holiday all round!
Top guest favourite
Farm stay in Palaia
4.98 out of 5 average rating, 169 reviews

Countryside Dream farm in Tuscany

MercedesRating, 5 stars5 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! 🌿🍷☀️
Superhost
Farm stay in Monteriggioni
4.82 out of 5 average rating, 149 reviews

Podere Casalino - La Pergola

GeorgieRating, 5 stars9 months ago
Laura and Jeremy’s Airbnb is so special and we are so glad we had 5 nights here. It’s the location, the house, it’s surrounding, the vegetable patch, dogs, incredible pool and Laura + Jeremy themselves that make it so lovely. The villa became our home base and was so peaceful and calm with everything we needed. It was the type of experience that made us want to move in forever. Jeremy even brought us fresh tomatoes and herbs from the garden, bellissimo! If you are reading this review, please do yourself a favour book. Recommend a hire car and buying produce to cook up some delicious meals to eat under the Tuscan sun 🌞
Guest favourite
Farm stay in San Gimignano
4.89 out of 5 average rating, 209 reviews

Oleandro double room with pool in San Gimignano

EricaRating, 5 stars1 week ago
While Paolo was away, our check-in and communication with Bruno went very smoothly. The property is absolutely stunning. The view of Sam Gimignano as you swim in the pool was something out of a movie scene. The property has surrounding olive trees and vineyards seen right from the window of the airbnb. This particular room is in a tucked away corner of the property and feels very private. Bed was comfy. Washing machine and drying racks, as well as a grill were plusses. Many agriturismos offer a dinner for an added fee, and we were a little disappointed that the dinner (in the past offered by Paolo’s neighbors) was closed during our stay. However, in fending for ourselves, we did appreciate the mini fridge and microwave, and loved eating our dinner right on the private table outside the room door. Also, you do have to clean out your trash at the end of the stay. Price felt right. Overall, would happily stay again and will be forever dreaming of the view.
Guest favourite
Flat in San Gimignano
4.89 out of 5 average rating, 126 reviews

Apartment Ortensia

JérômeRating, 5 stars3 weeks ago
Roberto et sa femme sont sympathiques, attentionnés et accueillants. Le lieu est magnifique et très intéressant pour rejoindre San Gimignano à pieds. Nous avons passé un formidable moment. Nous recommandons !
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 ❤️

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

  • Total rentals

    550 properties

  • Nightly prices starting at

    ₹866 before taxes and fees

  • Total number of reviews

    26K reviews

  • Pet-friendly rentals

    200 properties allow pets

  • Rentals with a pool

    60 properties have a pool

  • Rentals with dedicated workspaces

    300 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Siena
  6. Family-friendly rentals