House holiday rentals in Gaiole in Chianti

We had an absolutely amazing time at Daniela’s place - it was clean, had stunning views and was quick access to Pisa, Florence & Siena. Beautiful pool and lovely terrace with amazing views and sunsets. The kitchen also had everything we needed, including local olive oil and pasta & local wine as a welcoming gift. Daniela went above and beyond providing us with lilos and a pump for the pool too. Overall, 10/10 stay!

Martina’s entire estate is very peaceful and extremely beautiful. Just remember that it is really off the beaten path. She was so passionate about the property and making people feel right at home. It was one of the more beautiful places we stayed in all of Italy. Make sure to bring food up there with you before going. It is at least 35 min to town, but this is one of those places it is almost not worth leaving. Wish we had more time to stay there.

Great place and location. everything about the place and our stay was excellent.

Everything was absolutely perfect! ⭐️ Location: Ideal base for exploring Tuscany — you’re right in the heart of it all. Whether you’re heading to Florence, Pisa, or the charming hill towns, everything is within easy reach. House: Well-equipped and comfortable, with all the listed amenities in perfect working order. After long days of sightseeing, the pool was a refreshing retreat. The panoramic view over the valley is truly breathtaking. Host: Lorenzo is an outstanding host — friendly, responsive, and fluent in English. He was proactive and helpful throughout our stay. The house includes a detailed guidebook he created with handpicked recommendations for local shops, markets, restaurants, farms, and sights. It made planning our days effortless. Bottom line: If this listing is available — don’t hesitate. Book it. 10/10 would recommend!

I don’t have the words to describe how beautiful this apartment on the hillside is. The apartment itself is nice and cosy and spacious, and the kitchen contains a little bottle of olive oil produced from their own olives. But it is the location, the gardens and the little farm and the view across the valley which can take your breath away. Sonia is happy and welcoming and patient. She showed us around the wine and olive farm and was always approachable when we contacted her. There are two guest apartments side by side, but it is quite private nonetheless. Note that you can hear sounds from the other apartment quite easily. I cannot recommend this enough! Would love to come back.

Ein unvergesslicher Aufenthalt im Herzen der Toskana! Die Wohnung liegt traumhaft schön in der Natur – umgeben von sanften Hügeln, Weinbergen und unzähligen Olivenbäumen, die in der Sonne silbern schimmern und das Landschaftsbild einfach magisch machen. Die Aussicht ins Tal ist atemberaubend schön – man könnte stundenlang einfach nur dastehen und schauen. Der 28 Meter Pool? Besser geht es nicht – perfekt gelegen mit Panoramablick, absoluter Ruhe und einer Atmosphäre, die zur puren Entspannung einlädt. Was diesen Ort aber wirklich besonders macht, sind die Menschen: Jacopo, Sophia und ihre Kinder haben uns mit einer so herzlichen Offenheit empfangen, dass wir uns sofort wie bei guten Freunden gefühlt haben. Es ist einfach schön, solchen Menschen zu begegnen – authentisch, warm und voller Lebensfreude. Und dann war da noch Luba, die Schäferhündin – ein echtes Herz auf vier Pfoten! Sie hat uns jedes Mal mit solcher Freude empfangen, dass wir sie sofort ins Herz geschlossen haben.

Très bon séjour passé chez Giulia. Maison agréable et spacieuse. Bon emplacement pour découvrir le Chianti et ses chemins blancs.

Wir hatten eine wunderbare Zeit in diesem absolut niedlichen Haus, das inmitten atemberaubender Natur liegt. Die Ruhe ist einzigartig – man hört nur das Zwitschern der Vögel, und hin und wieder zeigen sich Rehe am Waldrand. Einfach magisch! Der Pool war top gepflegt und man hatte richtig Ruhe. Ein echtes Highlight war für uns die Küche: So liebevoll eingerichtet und außergewöhnlich gut ausgestattet – das haben wir so noch nie erlebt! Der Gasherd und der hochwertige Backofen haben das Kochen zu einem Vergnügen gemacht. Gastgeber Diego war unglaublich freundlich, aufmerksam und herzlich. Man fühlt sich bei ihm sofort willkommen und bestens umsorgt. Ein perfekter Rückzugsort für alle, die Natur, Ruhe und liebevolle Details zu schätzen wissen.

We had a brilliant week at Jakob and Margit’s house. Margit was so friendly and helpful (and gave us some wine and fresh eggs!). The views from the gardens are incredible and having the swimming pool was perfect. The local area has lots of great vineyards to visit and the house is close to Florence/Siena/Arezzo for day trips. It had everything we needed like a washing machine etc.

Es ist ein Fußmarsch von 1,6 km vom Ortskern Gaiole hoch zum Ferienhaus (die letzten 600m davon ziemlich steil), für einigermaßen sportliche Menschen sehr gut zu bewältigen ( und mit dem Auto GAR KEIN PROBLEM, (wir fahren Skoda Oktavia)). Wir sind den Weg mehrfach gelaufen, ein super Verdauungsspaziergang nach dem Essen im Ort, begleitet von tanzenden Glühwürmchen und Kauz-/ Eulenrufen im Mondlicht. Oben angekommen wartet ein Paradies/Rückzugsort/Ruhepol zu dem alles bereits beschrieben wurde (auf jeden Fall an Mückenschutz denken)....Wir sind total begeistert, das Essensangebot von Mama ist gerade für den Anreisetag eine super Idee, wir kommen gerne wieder. Herzliche Grüße an Edoardo und Familie

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!

How can we even put into words what an incredible experience this was! Antonella was kind and helpful, and her home is just stunning. She made us feel so at home even with our limited Italian. She prepared us a home cooked, four-course meal one night and it was absolutely delicious. She even gave us the leftovers so we could have them for breakfast the next day. The villa was breathtaking and in a perfect location to visit beautiful towns in Tuscany like Pienza, Montepulciano and San Gimignano. We especially loved the pool and visiting with the animals. This was a bucket list stay for us and worth every penny!

Beautiful home. Extremely clean. Riccardo was extremely responsive and made our check in process very easy. Definitely would stay again!

È stato molto piacevole soggiornare con i miei amici nell’ alloggio di Tania con il parcheggio in strada , ma che sembrava quasi essere privato .L’appartamento , moderno e funzionale è pulito e ben attrezzato con un giardino curato . Lo consigliamo vivamente

Great location only 2 minutes walk from the Cathedral. Accommodation is airy and well equipped with its own lovely garden giving you a great place to relax so close to the centre. Francesca was always available and made us feel very welcome. Have already recommended this property to our friends.

Danke Pietro für unseren schönen Aufenthalt in deinem Zuhause in Casole! Wer die Chianti-Gegend in all seiner Authentizität erleben will, der ist bei Pietro genau richtig. Die Wohnung ist etwas abgelegen, dafür in der wunderschönen rauen Natur von Chianti. Von dort aus kann man viele Weingüter erkunden, aber auch wandern und schöne Sonnenuntergänge genießen. Pietro sehr freundlich und nett. Vielen Dank!

Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.

The area is incredible, peaceful and the view spectacular. Asciano has the delightful charm of an Italian village. The people were friendly and welcoming. Even got greeted by their local police who offered up their number in case we needed anything. I felt safe, and it felt as if I lived there for years. I’d say this is a piece of heaven on earth. Bellezza maestosa! Non vedo l'ora di visitare di nuovo la Toscana e la città di Asciano! Grazie!

Uno de los mejores lugares en los que nos hemos quedado y explicó porqué: Monia y su hija Giusy han sido muy amables, buenas anfitrionas y responden rápido. El lugar nos ha encantado: perfecto para desconectar y pasar rodeados por naturaleza en una casa grande, limpia y cómoda. Además, la casa ha venido muy bien abastecida, sobre todo la cocina: nos dejaron muchas cosas para desayunar y también para la cena, que nos alcanzó para más de un día sin tener que ir. hacer la compra del supermercado! También como padres valoramos mucho que la cuna para nuestra bebé haya sido de las de madera, con su colchón y todo, como en casa. No era una cuna de viaje, así que resultó súper cómodo para nuestra bebé. Asimismo, tenían un cambiador y trona, que nos vinieron genial. En una futura oportunidad, seguro repetiremos!

Elena's Airbnb is great! The location is perfect for trips around the Tuscan countryside, and you'll be surrounded by peace and quiet. Even though it’s a small town, there are good restaurant options and a supermarket very close by. The accommodation is small but very comfortable (ideal for 2 people, but we managed just fine with 4). It has everything needed for a great stay, including excellent internet. Parking is outside the property in an open area, but we always found a spot during the week we spent in Cavriglia. Elena is very easy to communicate with, gave clear instructions, and is a very kind person! The bottle of wine she left for us was the cherry on top! We recommend it with our eyes closed.

We had everything we needed for a very relaxing stay in rural Tuscany, away from the hustle and bustle of daily life. Our hosts, Alejandra and Filippo, were very welcoming, friendly and helpful with local recommendations.

Stella nos recebeu muito bem, foi simpática e prestativa. A casa estava muito limpa e organizada. O espaço e aconchegante. O lugar é extraordinário, muito bonito, com natureza exuberante e uma vista maravilhosa. Stella recomendou lugares para visitar e restaurantes da região que gostamos muito. Somente elogios, nenhuma reclamação.

Amazing place. clean, all new and equipped. Remote quiet area with a swimming pool mostly was for ourselves. A gem. Tommaso and Simone were great. Nothing else to ask for. Highly recommend!!!

Wir hatten eine wirklich wunderbare Zeit in der Unterkunft! Sie ist genauso wie auf den Fotos: Sehr schön eingerichtet, ruhig und mit tollem Ausblick. Eines der schönsten Airbnbs, in denen wir bisher waren! Der Pool war leider geschlossen, dafür kann man aber in den umliegenden Seen schwimmen gehen. Wir waren nur zwei Nächte dort, wollen aber ganz sicher noch einmal wiederkommen und dann auch länger bleiben!