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Family-friendly holiday rentals in Trequanda

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Trequanda family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
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 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
Condo 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.
Top Guest favourite
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 favourite
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 favourite
Villa in Montepulciano
4.91 out of 5 average rating, 126 reviews

Villa a Montepulciano con Piscina

SantiagoRating, 5 stars1 week ago
We just checked out of this wonderful villa today, and it has truly been one of the most special places we’ve ever stayed. We arrived with my husband’s parents, my husband, and our toddler, and from the moment we got there, everything exceeded our expectations. Alex greeted us warmly, gave us a tour of the villa and the property, and provided detailed printed information about nearby restaurants, supermarkets, cafés, bakeries, and wine tours. The property also produces its own wine, which was available for purchase and could be conveniently delivered to our villa during our stay. Alex shared his contact number and made himself available in case we needed anything—which we really appreciated. One of the highlights of the property was the stunning infinity pool overlooking the vineyard and offering breathtaking views. It was the perfect setting to disconnect and truly live in the moment. The air conditioning and hot water worked perfectly. Thank you Alex!
Superhost
Villa in Baschi
4.87 out of 5 average rating, 176 reviews

VILLALADOLCEVITA

SimonRating, 5 stars2 weeks ago
Very nice stay for a few days relaxing in summer. Beautiful olive gardens around the house, nice collection of wine. Everything clear, super big house, will come back next year!
Top Guest favourite
Condo in Chiusi
4.95 out of 5 average rating, 148 reviews

La Terrazza su Chiusi - appartamento panoramico

DianneRating, 5 stars1 month ago
Chiusi may not be a major hilltop town but it is very special because it lacks the tourists. We had plenty of restaurants to visit in the week we stayed, and lots of historic sights to see. You do need a car to visit surrounding towns but the peacefulness of Chiusi makes it delightful. Rafaels place is perfect with the balcony and sublime views. He was an exceptional host who did not impose on our privacy but always friendly and helpful. I would highly recommend this place and town.

Family- and pet-friendly home rentals

Guest favourite
Apartment in Pienza
4.9 out of 5 average rating, 170 reviews

Back Home - Apartment in Pienza

CharmaineRating, 5 stars2 weeks ago
Valeria was a very helpful host, always responds to any questions we had. The house is close to Pienza's city centre while being in a cozy neighbourhood so really enjoyed the location. It was really close to the bus stop as well. The rooms in the were also spacious and beds were clean.
Top Guest favourite
Castle in Montecatini Val di Cecina
4.99 out of 5 average rating, 118 reviews

Torre dei Belforti

JoyRating, 5 stars4 days ago
What a wonderful week we had with Luca and Emilia at the tower! It was amazing to see all the pictures in real life - it was even more amazing in person. And the garden is just magical. I had no idea the beauty of the pool area. Laying by the pool and listening to nature we felt transported to a simpler time. To top it off Luca was so delightful. We enjoyed his company and hearing more about the story of the tower and the town. I would recommend this as a stop on anyone’s vacation to Italy. Wonderful hosts in a magical setting!
Guest favourite
Home in Cerreto Guidi
4.95 out of 5 average rating, 474 reviews

Casa del Giardino

LoriRating, 5 stars1 month ago
My husband and I, plus our French Bulldog, had the pleasure of staying here for just over 3 weeks. Immediately felt like home, and host family had everything to do with that! Highly recommend. stunning views, fabulous location and some of the most gracious people I've ever met.
Top Guest favourite
Villa in Sarteano
4.97 out of 5 average rating, 125 reviews

Casale in pietra in Val D’Orcia

Theng JuhRating, 5 stars2 weeks ago
Stefania was super nice to wait for us despite we were later for 3 hours. Her house was very beautiful and lots of space for 10 of us. Everyone can have their own space on the balcony or terrace. Can have BBQ too. House was very well equipped with everything that we expected. Had a wonderful time. Thank you.
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!
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.
Superhost
Farm stay in Castiglione d'Orcia
4.89 out of 5 average rating, 229 reviews

agriturismo il poderuccio monolocale

RachelRating, 5 stars3 weeks ago
Great stay! Initially the place was a bit further out of town than we had anticipated but we still found it very accessible to lots of the things we hoped to do! The view was amazing! So peaceful to sit on the terrace!
Guest favourite
Farm stay in Pienza
4.94 out of 5 average rating, 172 reviews

Agriturismo Palazzi del Papa Val d'Orcia Pienza

AntiamRating, 5 stars2 months ago
Wir hatten eine fantastische Zeit in Sabrinas Unterkunft in der Nähe von Pienza. Sabrina war stets erreichbar und extrem freundlich & proaktiv. Die Räumlichkeiten waren tiptop sauber. Das Frühstück wurde stets frisch zubereitet. Der Garten und die Aussicht waren atemberaubend. Alles in allem haben wir die Zeit extrem genossen. Zwei kleinere Bemerkungen: - Die Preise für den Kochkurs empfanden wir doch noch ein bisschen mit 100 Euro p.P. im teuren Segment (100 Euro p.P.) - das war uns leider nicht im Vorhinein bewusst, evtl. wäre es gut ein bisschen mehr Transparenz zu gewährleisten. - Es gab an zwei Tagen komplette Wasserausfälle für viele Stunden - an sich nicht schlimm, aber sollte hoffentlich nicht die Norm sein.

Family-friendly home rentals with a pool

Superhost
Home in Asciano
4.88 out of 5 average rating, 144 reviews

A Charming House in Asciano - Siena

CristinaRating, 5 stars8 months ago
Very nice place with a great view, very quiet and relaxing. The apartment was clean and cozy. The only inconvenience were the squeaky doors.
Top Guest favourite
Farm stay in Palaia
4.98 out of 5 average rating, 169 reviews

Countryside Dream farm in Tuscany

MercedesRating, 5 stars1 week 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
Apartment in Montepulciano
4.84 out of 5 average rating, 99 reviews

La Casa delle Querce - "Belvedere"

OceaneRating, 5 stars8 months ago
Un superbe endroit qu’il est difficile de quitter. Nous avons adorer séjourner dans ce magnifique logement typique de la Toscane et une vue magnifique sur ses environs. Nous y retournerons avec plaisir si l’occasion se présente. Luca est une personne chaleureuse et très attentive. Nous recommandons.
Top Guest favourite
Home in Asciano - Chiusure - Monte Oliveto Maggiore
4.96 out of 5 average rating, 182 reviews

Country House in the Crete Senesi

CharlotteRating, 5 stars1 month ago
We feel so lucky to of found Guido and his beautiful house. Firstly Guido could not be more helpful, so responsive, friendly and has the best recommendations! He made sure the house was spotless for our arrival, even the pool is so clean it was perfect. The house itself is stunning, stays lovely and cool in the heat but the garden is just drenched in sunshine. Guido has made sure you can bask in the sunshine by the pool or chill out in shade in the height of the afternoon. There are so many comfortable spots to sit in! The pool was lovely and refreshing when it was hot mid afternoon and looked beautiful in the evening. Tuscany is stunning, there's so much to explore - would heavily recommend a car for that. In walking distance there are a couple of very delicious restaurants and if you're feeling adventurous you can walk to the monostary nearby which is definitely worth visiting. Thank you Guido!
Top Guest favourite
Apartment in Barberino Val d'Elsa
4.99 out of 5 average rating, 122 reviews

Appartamento nel Chianti al Mulino dell'Argenna

MarkusRating, 5 stars2 weeks ago
Wir waren nun schon zum zweiten Mal in der Unterkunft von Elisa und Alessandro – und es war wieder einfach wunderschön und absolut erholsam! Der Ort ist eine richtige Oase, in der man perfekt abschalten kann. Elisa und Alessandro sind äußerst hilfsbereit und herzlich. Sie haben uns mit tollen Tipps für Unternehmungen und Restaurants versorgt, sodass wir unseren Aufenthalt rundum genießen konnten. Wir kommen sehr gerne wieder und können diese Unterkunft nur wärmstens empfehlen!
Top Guest favourite
Farm stay in Reggello
4.96 out of 5 average rating, 163 reviews

Colonica in pietra, piscina privata in esclusiva

MeganRating, 5 stars2 weeks ago
We absolutely loved our stay at this property in Reggello! The hosts were so warm and communicative—they greeted us upon arrival and gave us a full walkthrough of the home! The view was stunning, and the pool was beautiful and very clean. Aldo even came by each morning to clean it before we used it, which was such a thoughtful touch. Everything in the house worked perfectly—the Wi-Fi was fast, all the appliances and lighting functioned well, and we had no issues during our stay. The drive from Florence was easy (we had a rental car), and it made exploring nearby wineries and towns super convenient. We also LOVED their on-site farmers market. It was their own personal setup with wines, olive oil, jams, and other homemade goods -- plus fresh produce like eggs, garlic, artichoke, & shallots, which they generously offered free of charge. We’d definitely stay here again and highly recommend this property to anyone looking for a peaceful and scenic escape in the Tuscan countryside!
Guest favourite
Guesthouse in Antria
4.92 out of 5 average rating, 130 reviews

A charming Tuscan retreat

janeRating, 5 stars2 weeks ago
A very peaceful retreat in a beautiful garden with lots of private places to sit or eat and an extended view over the valley towards Arezzo and mountains beyond. Caroline was helpful but did not intrude. The cottage has an authentic Tuscan style and furniture to match and although quite dark there are big windows looking out onto the garden and view. We enjoyed using the private pool and exploring the local area as well as a National Park to the north (lovely beech forest) and Siena. The TV isn’t ‘smart’ and there is no dishwasher but this is reflected in the price (however there’s a large book collection including lots of guidebooks). It was a very relaxing stay for us, thank you.
Top Guest favourite
Apartment in Montepulciano
4.92 out of 5 average rating, 157 reviews

Romantic apartment in a quite place

MelissaRating, 5 stars1 week ago
We had such a lovely stay at Paolo's place in Montepulciano! The location was beautiful and the pool was a highlight! They also had a little playground which was great for our toddler. Paolo was very welcoming and gave great recommendations for places to eat. They grow olive trees on the property, so they provided a little bottle of homemade olive oil in the kitchen, which was delicious! Thanks for having us and we hope to come back in the future!

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

  • Total rentals

    180 properties

  • Nightly prices starting at

    $116 NZD before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with a pool

    150 properties have a pool

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

Destinations to explore

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