
Family-friendly holiday rentals in Gaiole in Chianti
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Top-rated family-friendly rentals in Gaiole in Chianti
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Family-friendly home rentals with a hot tub

Bioagriturismo colline Firenze 3p
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!

Il Fienile, Cottage in the country with Jacuzzi
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!

Torretta Apartment
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!

Splendido fienile ristrutturato in Toscana
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!

Wheelchair accessible Villa with Jacuzzi
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.

Ancient Tuscan Rural Residence
This is such a lovely place to stay. I was so happy to look at the surroundings with breathtaking views and the tranquility ( besides the fogs ) makes this place a paradise . The house was very spacious and confortable . The jacuzzi is really a plus and the swimming pool perfect . Francesco and Serena were so helpful to find activities for our family . The communication was great . I really recommend this place … soooo beautiful !

La Casetta
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, ...)

Domus Nannini - Loggia Salimbeni SPA
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

Torre dei Belforti
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.

Casa del Giardino
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.

Esplora la natura al centro di Vigneti Chianti
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.

PODERE GUIDI
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.

Casa Al Poggio & Chianti view
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.

Stuart White Tea Central Panoramic & Garden
My wife, brother-in-law, and I had an incredible time in Montepulciano, and Giacomo’s apartment was the perfect place from where we started out daily adventures, took afternoon naps, and then headed out for fantastic dinners. Giacomo’s apartment was excellent, making it easy to get settled after a long day of travel. Giacomo guided us into the temporary parking spot when we got lost for a few minutes, and was quick to assist with any questions we had during our stay. The restaurant recommendations were all excellent, as well as the other activities he suggested. We will definitely stay here again when we visit Montepulciano!

casa mezzomonte Apt Timo
아름다운 자연환경 속 영화에 나오는 것 같은 집에서 행복한 시간을 보냈습니다. 친절하고 다정한데 응답도 너무 빠르신 호스트 덕에 끼안띠에서의 시간을 좋은 기억으로 간직하게 될 것 같아요. 숙소를 찾아가는 길이 초행인 도시녀들에게 처음엔 조금 힘들었지만, 익숙해지니 어렵지 않았어요. 일출과 일몰을 보기에도 완벽. 오늘 떠나왔지만 또 다시 가고싶어요.

Country house 9 km to Florence-2+1g,free parking
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!
Family-friendly home rentals with a pool

Farmhouse with swimming pool with wonderful view
Wowww , nous sommes déçu de ne pas avoir réserver plus longtemps , le spot est parfait pour visite la toscane( avec une voiture bien sûr ) Les journée plus chaude nous avons fait de la piscine , leur déjeuner étais excellent !!! C’était exceptionnelle !!!

loft nel cuore del chianti toscano
Très bon séjour passé chez Giulia. Maison agréable et spacieuse. Bon emplacement pour découvrir le Chianti et ses chemins blancs.

Agriturismo I Gelsi
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!

Colonica in pietra, piscina privata in esclusiva
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!

Villa Poggio a Mandria in Chianti
A beautiful place, beautiful surroundings, great hosts, great pool, just everything was perfect. Didn’t want to leave. Felt like home and couldn’t wait to get back there on the days we ventured out.

Visit Chianti,Siena, Florence, S.Gimignano
Franco's place exceeded our expectations! The surrounding views were breathtaking. We loved the fantastic amenities, especially the pool and ping-pong table, which were great for recreation. The location is perfect, being very close to San Donato, renowned as one of Italy's most beautiful towns. We discovered numerous neat spots to taste and buy local wine! A quick tip for future guests: plan your meals as finding food spontaneously can be tricky, and a vehicle is definitely recommended for getting around.

Paluffo Stillo House
Don’t hesitate to book this beautiful Airbnb which was thoughtfully restored to reflect the history of the area. You won’t want to leave. We explored Certaldo Alto and Montefioralle- both amazing sites. The pool area was perfection and we couldn’t get enough of the landscape! Couldn’t stayed a week!!!

Paradiso nel Chianti
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 Gaiole in Chianti
Total rentals
10 properties
Nightly prices starting at
$116 NZD before taxes and fees
Total number of reviews
140 reviews
Rentals with a pool
10 properties have a pool
Wi-Fi availability
10 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
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- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Basilica of Santa Maria Novella
- Mugello Circuit
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cavallino Matto
- Teatro Verdi
- Palazzo Vecchio
- The Boboli Gardens
- Spiaggia Marina di Cecina
- Santa Maria della Scala