Villa holiday rentals in Castellina in Chianti

Incredible host and property. We feel fortunate to have had the opportunity to stay here. Cesare was beyond helpful with recommendations and flexible with our check in. Secluded, peaceful and a great place for making memories during our travels around Italy.

Most beautiful villa with so much charm! Fantastic location as well, easy to explore Florence, Siena, San Gimignano, as well as all the surrounding wineries and countryside. The villa was so lovely that we decided to spend 2 days in the villa, chilling at the pool drinking wine and having tapas! Janine is a great host with many recommendations of what to do in the local area. Highly recommended to stay here to experience Tuscany!

The Lazy Oak Villa is everything we dreamed of and more for our honeymoon. The house is beautiful, well furnished and feels so homely and comfortable. The surroundings are simply stunning; the view from the house and pool never get old! Mario and Alessandro were super helpful, offering to help us book restaurants and vineyards if needed. Mario keeps to himself so still feels very private but is happy to help with anything and it was nice to see him around (with his cute little dog!) and know he was about if we needed anything. Couldn’t recommend the Lazy Oak Villa more, and we’re already talking about when we could come back!! Thank you Mario and Alessandro!

This property exceeded our expectations with spectacular views and peaceful, natural surroundings! The host was friendly and responsive. The proximity to San Gimignano and other Tuscan destinations was convenient. Each day felt magical! Just sitting on the patio was amazing! An unforgettable destination and experience!

I cannot say enough about our trip to Martino’s villa. What a lovely villa in the cute town of San Casciano dei Bagni. We had a great family vacation, enjoying some of the smaller towns and a visit to Montepulciano . We enjoyed Eleanor’s cooking for us two nights- what an amazing chef! Martino was very responsive and helpful when we needed something. I hope we can return one day!

Das Haus ist schön und sehr gross. Es liegt etwas ausserhalb von Buonconvento und bietet absolute Privatsphäre. Ein Auto ist von Vorteil. Die Zimmer sind grosszügig, es gibt Mückennetze über allen Betten und genügend Badezimmer und WCs für alle. Generell ist das Haus sehr gut ausgestattet, sowohl in der Küche als auch sonst. Der Pool ist etwas erhöht, schön, gross, mit natürlichem Schatten rundherum und bietet eine herrliche Aussicht auf die umliegende Landschaft. Im riesigen Garten kann man Essen, Verweilen, Spielen... Es gibt sogar einen kleinen Basketball-Court. Aber Achtung: Gleich nebenan gibt es wilde Brombeeren und der Ball kann verloren gehen :) In Buonconvento gibt es einen Coop, eine feine Gelateria und eine gutes Caffé mit den berühmten und feinen Produkten von Le Dolcezze di Nanni. Für eine gute Pizza lohnt sich die Fahrt ins Restaurant Mulinum etwas ausserhalb, sie haben eine eigene Mühle und verarbeiten ihr eigenes Getreide. Wir können das Haus sehr empfehlen.

En mycket bra upplevelse att bo hos Sandrine och Emanuelle. Tack! Jättevänligt bemötande och en plats som vi verkligen vill tillbaka till! Utsikten, huset, poolen och tomten omgiven av oliv och- vinodlingar. 6 stjärnor om det gick att dela ut!

Unser Aufenthalt in diesem wunderschönen Haus in der Toskana war einfach traumhaft! Das Haus liegt idyllisch am Land und hat all unsere Erwartungen übertroffen – es war noch schöner als auf den Bildern. Alles war sehr geschmackvoll eingerichtet, sauber und perfekt ausgestattet, um entspannte Tage inmitten der toskanischen Natur zu genießen. Die Gastgeber waren ausgesprochen freundlich und hilfsbereit – von der unkomplizierten Ankunft bis hin zu tollen Tipps für Ausflüge in der Umgebung waren sie immer für uns da. Wir können dieses Haus wärmstens weiterempfehlen und würden jederzeit wiederkommen!

This was our second time visiting Mogens and Suzie's beautiful home in Cortona. One reason for coming back was the sheer beauty of the property and the proximity to fantastic medieval towns with incredible history that endures even now. For wine enthusiasts, there are tons of wine tasting opportunities with lunch, dinner or just great wine. Another reason for our return visit was an opportunity to spend time again with Mogens and Suzie, by far the best AIRBNB hosts we have ever encountered. They do everything imaginable to make your time as enjoyable as possible and to say that they go the extra mile would be a gross understatement. We can't wait to come back a third time.

Caroline's villa was absolutely stunning. We visited as a family of 8 adults and it was even more beautiful in person. It's completely private with amazing views all around. It's also in a great location to visit other picturesque villages nearby with a car. The pool was a great addition to combat the Tuscan heat. As this is in the countryside, be aware that there will be insects and wildlife. We came across a snake and a scorpion, but that's not an issue with the house, but rather the natural environment. The property manager Bianca greeted us upon arrival. She was super friendly and helpful with tips. And Caroline left us super detailed recommendations for restaurants, itineraries, and wineries. She was always available and friendly. We had an amazing time and would definitely visit again!

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.

We had an amazing time in the villa from Tommaso. It has all the amenities that you expect from a villa in this price class. The view looking over the valley is beautiful. The communication with the host was very pleasant and swift. As an example; The existing tv got broken in the evening and the next morning Tomasso installed a new one with all the modern features like Apple Airplay. Since the weather was not great the first days you can imagine that this was very nice to have a good working tv. Anyone who is considering renting a villa in the surrounding of San Donato, I highly recommend this villa from Tommaso.

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!

Olga's villa is absolutely stunning. Our family of 9 had the most wonderful visit. We enjoyed cooking in the beautiful and well appointed kitchen, eating outside on the terrace, swimming in the pool, and relaxing outside on the terrace, enjoying the peaceful beauty and breathtaking views of Tuscany. Olga's place is truly special. Olga was very communicative, helpful and kind. We highly recommend her villa to others.

This was true Tuscany! We enjoyed the quaintness of the village with amazing restaurants and views! Tony transported us to and from the villa! Seamless planning. Deborah arranged transportation for us to visit other villages where we enjoyed the day, people and food! Wished we had more time!!

Family of 5 here, 3 small kids. A wonderful stay! We toured surrounding villages in the morning and came back to the pool to beat the heat in the afternoon. The private cooking class with Valentina was the absolute highlight of the trip!

Es war für uns als kleine Familie mit einem kleinkind ein sehr schöner Urlaub. Unsere Tochter liebte das Haus und die Umgebung. Trotz kurzen Aufenthalt fühlten sich die Tage wie zwei Wochen Ferien an. Wir kommen auf jeden Fall wieder. Die Gastgeberin war proaktiv und hat uns in allem was wir benötigt hatten unterstützt. Es hat uns an nichts gefehlt. Wir können es wärmstens weiterempfehlen.

We had an amazing four weeks staying at Bellagatta, using it as a base to explore Tuscany & surrounds, and it met all our expectations and more. Bellagatta is a positioned on a hilltop with stunning 360 degree panoramic views, more beautiful than the photos. The annexe that we stayed in was exceptionally clean and comfortable and well fitted out. Air con was useful on the first few days of our stay which were very hot. The property is well situated, 10 minute drive into Buonconvento (not quite an easy return walk up the hill!) which was convenient for restaurants & shopping. Gaetano was a most delightful host, very welcoming, & always taking interest in which towns we were travelling to and providing useful tips for our visits. His property manager, Susil, was also readily available and looked after us with anything we needed , even providing fresh eggs, vegetables & olive oil from the property. Highly recommended!

Wir haben uns sehr wohl gefühlt bei Beatrice und Alessandro. Es ist ein wunderbarer Ort um Urlaub zumachen! Wir werden definitiv wieder kommen!

Wir hatten eine sehr schöne Woche in der Unterkunft. Alles war sauber und da das Apartment mitten in der chianti Region liegt, konnten wir viele Ziele in der Toskana schnell mit dem Auto erreichen. Die Unterkunft liegt ruhig inmitten von Weinbergen und Natur. Rosita und Maria waren jederzeit erreichbar und sehr nett. Der Wein und die cantucini bei ceck in waren ein süßes und leckeres extra. Der eingezäunte Garten war auch für unseren Hund super :) fliegengitter an den Fenstern wären noch super gewesen aber allen in allem hatten wir eine wunderbare Zeit und würden wiederkommen!:)

Wir waren mit unserem Ferienhaus von Stefania sehr zufrieden. Toller, weitläufiger, uneinsehbarer Garten mit vielen Olivenbäumen. Pergola mit Sitzecke lädt zum verweilen ein. Auch die Sauberkeit der Unterkunft war ausgesprochen gut. Die Betten bzw. Matratzen waren sehr bequem und die Schlafzimmer schön eingerichtet. Stefania hat uns mit vielen Tipps und Empfehlungen versorgt. Sie hat für uns auch zweimal einen Tisch in der nahe gelegenen Osteria di Valgiano gebucht. Tolles Essen zu einem günstigen Preis mit tollem Blick über Lucca. Auf Fragen hat Stefania schnell und freundlich reagiert. Wir wären gerne noch länger geblieben und kommen bestimmt wieder!

A beautiful home to base ourselves in while exploring Tuscany. Lovely country surrounds. House has everything you need, spacious. Gorgeous terraces and pool. Enjoyed Volterra, San Gimignano and Siena but always great to come back to our Tuscan home! Silvia gave fantastic recommendations - pasta making at Ristorante de Beppino and in house chef Beppe highlights. Also loved Monterosola winery tasting. Very highly recommend. One of the best!

Barbara’s place was above and beyond our expectations in every way! If you are looking for a place to stay in this general area, don’t hesitate! Barbara was a wonderful host and all the instructions were very clear. The kitchen is very well stocked and we cooked all of our dinners there as we were traveling with a baby. We spent a lot of time hanging out as a family and there was more than enough room for us and both sets of grandparents. The home is very well situated and we loved exploring. There are so many great restaurants in the area. I can’t over state the beauty of the area and the house itself…my family is already dreaming about coming back!

A Perfect Holiday – Like Heaven on Earth! This place exceeded all our expectations. A stunning and peaceful location with breathtaking views over the valley, lake, and mountains. The house and garden were beautifully maintained, and the accommodation was very clean and comfortable. A special thank you to Mrs. Lesley, who was an invaluable help throughout our stay. She provided us with plenty of useful tips and advice on various matters, such as train tickets and local attractions. Thanks to her, we were also able to arrange a wonderful dinner at the villa – truly an unforgettable experience. We wholeheartedly recommend this place – if we could give it 150%, we absolutely would!