Villa vacation rentals in Gaiole in Chianti

There were 10 of us staying in Simone’s villa and it was such a lovely place to relax. The outside area was huge with many different seating areas. The pool looking over the town below was stunning. Simone was really responsive to any questions we had and gave us suggestions for wine tours and taxis. The indoor kitchen is a little small but still has everything you need. We used the outdoor bbq and pizza oven much more as this was perfect for cooking outside in the sunshine. Thank you for a great stay!

Incredible property with a breath taking view over Florence. Hard to put into words how perfect the property is but the best part of the whole experience was the hospitality Marco, Stefania Grinza Carota and Filippo! The best hosts imaginable made us feel so at home, welcome and a part of the family. Now we want to move to Florence

Entspannend, angenehmer Aufenthalt mit toller Aussicht, schön angelegtem Garten und nicht zu weit von Siena entfernt

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.

There are very few times when a stay not only lives up to expectations, but exceeds them. Our stay at the Lazy Oak did just that. There are no adjectives to truly describe the beauty of the villa and the surrounding countryside. Sitting at the infinity pool, looking out over the olive groves before a dinner prepared in house by a Tuscan chef as the sun sets will go down as one of the greatest days of our lives. We visited the nearby town twice for gelato but the truth is we did not want to leave the property! If you are looking for a peaceful quintessential Tuscan vacation in the countryside, look no further than the Lazy Oak. Mario is on property to tend to any needs but keeps to himself unless called upon. We actually loved his company and called him over to talk on multiple occasions…with the help of Google translation of course. Thank you Mario and Alesandro for an unforgettable stay. We hope to see you again in the future.

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!

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.

Beautiful property. Staff were amazing, responsive and friendly. Location ideal for visiting other cities by car. Exactly as pictured. Breakfast which was added on a day to day basis was spectacular. Very relaxing sitting on patio and by the pool.

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!

Villa Adagio is zoals je je een Toscaanse villa voorstelt en dan nog beter! Prachtige villa met heel veel ruimte binnen en buiten. Het zwembad deel je met eventuele andere bewoners op het terrein. Er zijn enkele eigenaren van andere woningen en ook nog een ander huurappartement. Maar zelfs nu in augustus was het zwembad meestal verlaten. De villa heeft een gastenverblijf met badkamer waar onze jongens van 15 en 16 sliepen (volop privacy en geen hinder van lang kletsen en gitaar spelen in de nacht 😊). In het grote huis 3 ruime slaapkamers en 3 badkamers. Heerlijke woonkeuken met grote eettafel en natuurlijk de mooie loggia over de hele breedband het huis met prachtig uitzicht over de heuvels. Mijn favoriete plek! De villa ligt privé en vrij afgelegen. Dichtstbijzijnde dorpjes zijn een kwartier met de auto en daar vind je zowel winkeltjes om boodschappen te doen als prima restaurantjes. Iets verder rijden ligt het mooie Siena, maar ook Montepulciano en Arezzo zijn niet ver en heel mooi

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!

Vi er en familie på 5 som havde et helt fantastisk ophold. Huset er kæmpestort og meget flot og udsigten findes ikke bedre. Alt stress forlader kroppen når man er der. Alle vegne man kiggede var der exceptionelt flotte udsigter. Derudover var Lucia og Frederico så varme personer og gjorde at vi var meget velkommen. Vi kommer helt sikkert igen!

This is one of the most beautiful and unforgettable locations we have ever visited. To be able to wake up in a centuries old villa and look out over the hillside with olive groves and vineyards was spectacular. Janine was so helpful to meet us and help us get acclimated and then provide a list with local wineries, restaurants, small towns to visit and things to do. We are so very grateful for her hospitality and ready to book another trip soon. Thank you Janine for everything.

La Vignaccia is wonderful. We were a family of 6 adults plus a baby, and the set up was great for spending time together but also having plenty of space. The kitchen is well equipped for cooking for a large group and the many private spaces were very relaxing. Working remotely was possible with the wifi but not super strong for calls. However there is 5G around the house, so hot spotting from a window worked fine.

We had the most wonderful stay at Olga’s place. We had 6 adults and two children and there was still plenty of space. The house was beautifully appointed and the outdoor space with the view was the perfect place to relax.

Great place to stay. Excellent communication, went above and being to ensure our stay was exceptional. Deborah even bought a pasta machine for us to use for our evening meal - which was really appreciated. It was a great week.

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!

Laura was an amazing host and made sure we knew all the details of the house and was very responsive if we had a question. The house itself is gorgeous and so are the surroundings. Highly recommend staying here as a home base in the Tuscany area! We visited many surrounding cities as well as a winery 40 minutes south. We would also recommend the restaurant Nuevo Ranch right done the street! Wonderful!

We were a group of 8 staying at Villa Il Castellaccio and it was the most amazing experience. Leonardo was very helpful leading up to our stay helping plan a night with a private chef dinner. The food was some of the best we had! The Villa was private, more than enough space for our group and the grounds around the pool was always pristine. We highly recommend staying at this wonderful place. Our group already discussed coming back again and staying longer. Thank you Leonardo!

Bereits im Vorfeld wurden wir von Emanuele kontaktiert. Er hat uns die Wegbeschreibung geschickt, damit wir das Haus problemlos finden können. Wir wurden sehr herzlich mit regionalen Spezialitäten und Wein empfangen. Der Aufenthalt war super, wir haben uns sehr wohl gefühlt. Während des Aufenthalts haben wir ganz viele Tips bezüglich Essen und Ausflugsmöglichkeiten von Emanuele erhalten. Er war sehr hilfsbereit und immer erreichbar. Wir werden bestimmt wiederkommen.

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 thoroughly enjoyed our stay. The house is conveniently located in the heart of the Valdichiana with easy and clear access to the surrounding towns. The grounds were beautifully landscaped with a combination of olive trees, grapevines, flowers and even herbs like rosemary, basil and mint that we used in our cooking. The rooms were spacious and very private. Our group of 6 were more than comfortably accommodated, each with its own bathroom and AC units that worked well. The two kitchens served us well. We mainly utilized the outside kitchen as the weather throughout our stay was perfect. The kitchens were well stocked with all of the necessary cooking items. There were some items that we needed to purchase at the local supermarket, including shower gel, paper towels, napkins, etc. For a one week stay we would recommend extra towels, especially for the pool. Overall, I would highly recommend La Bacaia as a base to fully enjoy your Tuscan vacation.

We could not have asked for a more beautiful setting to celebrate my partner’s 40th birthday. Our week was perfectly balanced between visiting nearby Montalcino wineries & surrounding villages, a day trip to Siena, and lazing about the pool & villa. Monica was kind, generous & helpful from the time of booking. She accommodated all requests and even left a gift for my partner to celebrate his birthday! Will be back! Would rate this 6 stars if we could.