Vacation rentals with a pool in Castellina in Chianti

Simone was great during our stay. Super responsive and helpful. The space was beautiful and comfortable for 2 people. Also, central to bus stops that get you into the city within 10 or so minutes. Would definitely recommend!

I had the most amazing experience staying at this beautiful villa in Florence. The location was perfect—peaceful, private, and surrounded by stunning views that took my breath away, especially from the parking area. The villa itself was incredibly cozy and charming—so well maintained and full of character. Honestly, I didn’t want to leave. I’d live there if I could! The pool was a dream—relaxing, and the perfect spot to unwind with the Tuscan countryside all around you. Our host, Leonardo, was absolutely fantastic—so friendly, welcoming, and helpful throughout our stay. You can tell he really cares about making guests feel at home. This place was everything I hoped for and more. I would 100% come back again. Highly recommend!

Charming villa in total relaxation. Lots of green space and a beautiful pool... all just for us. Giovanni was super welcoming and kind. An experience to repeat, highly recommended! Greetings from Fede and Kevin

What a beautiful place. So tranquil. Despite other guests being in the other houses dotted around the same garden we never bumped in to them - it felt private and intimate. The garden is so beautiful, well looked after with good views down the valley. The house is cool and quiet, felt rustic and authentic but not dated or dusty, it managed to strike that balance really well. Lorenzo was super helpful and responsive, always quick to let us know about the place and had loads to recommend in the area. And Alba, the matriarch of this oasis, was just the sweetest and warmest person ever. So friendly and welcoming. She gave us both a big hug when we got there and I only wish I spoke some Italian to be able to thank her for everything. She brought us loads of delicious baked goods and just seemed so happy to have us there. Overall a really wonderful and memorable trip. The only regret is not booking one week later! The day we left the pool opened for the summer. We'll just have to come back!

I had an unforgettable stay at Casa Elisa, located at the foot of the beautiful Cortona. The atmosphere is magical: a perfect fusion of Tuscan tradition and modern comfort. The rooms are elegant and quite spacious, tastefully furnished and equipped with all the necessary comforts. The garden with pool is an oasis of tranquility, ideal to relax with a good book or to enjoy an aperitif at sunset. But it's the warmth and hospitality of Elisa's family that makes the stay really special. Their availability in providing information about places to visit and recommended restaurants makes all the difference. I highly recommend Casa Elisa to anyone who wants to discover the beauty of Tuscany, living an authentic and unforgettable experience.

We really loved our stay, the beautiful surroundings and the place was even better than the pictures. Alfredo was very responsive and friendly. Would really recommend if you’d like a peaceful stay with close proximity to local Tuscan villages to explore.

We absolutely loved our two-week stay at Lucy and Tommy’s house. The house itself is beautiful, and the garden is truly a haven of peace - we spent so much time there, fully unwinding and recharging. From the moment we arrived, Lucy and Tommy were wonderful hosts, always available and incredibly helpful. They provided great local recommendations, and we were also lucky enough to try their delicious homemade olive oil. The house is located in an extremely peaceful area, surrounded by trees and nature, which made our stay even more relaxing. We can only highly recommend this accommodation and we truly hope to visit again in the future.

Very pleasant house to stay in, extremely quiet, with superb views of Lake Trasimeno. It is excellently located, since in 30 to 60 minutes by car you can also be in Perugia, Assisi, Arezzo, Siena and so many other beautiful cities. And, for those who prefer to walk or cycle, the lake tour is almost 60 km! Last but not least, Sergio is very friendly, full of attention but at the same time very discreet, and as a man of culture he will give you all the information you would like. For a rental in the heart of Umbria and southern Tuscany, look no further, this is where you want to come. Annette and Michel

Nice scenary, quiet romantic Town, Nice small cafe beside the river. But what impress Me marco property I felt like Home right away. Secured electeric gate leaving Me no worries. Kids love it and kitchen are well equip!! Thanks marco for your beautiful place and hosting us!!! I recommend this place for quiet country side place.

Tuscan retreat = THIS. Set in a lovely, quiet area with gorgeous views of the landscape. Easy to get to Arezzo and only 1 hour from Florence. So many amazing local restaurants and Vineyards. The property itself has a traditional vibe to it. The kitchen is not well equipped, so just bare that in mind! minimal pots, pans etc. But otherwise looks exactly like the photos.

We had a great time at this beautiful place. The farm has several apartments, each with their own privacy. The pool was very clean and warm, there was shade available and a shower and toilet right next door. The apartment was as shown in the pictures, there was no air conditioning but it was very cool inside during the day. A few days before our arrival, Isabella sent us all the necessary information and it was her brother Piero who welcomed us very warmly upon arrival. The place was very clean, the kitchen well-equipped and towels were provided. There are many things to do and see in the area, we even had recommendations available. Overall we are really happy and would definitely recommend this place!

Wonderful place, very nice host. Thank you for your hospitality, Silvia

The place is really a dream! We had a lovely, relaxing time with Deborah. The pool and location are great and Deborah gives great recommendations, is totally warm and you feel right at home. And we liked it so much that we want to come back!

We had a lovely stay here - there were 8 of us in total across 4 spacious bedrooms and 3 bathrooms. It is a beautiful old villa with a big garden and a cute pool and barbecue area. It is possible to walk into the city of Florence (30 - 40 minute stroll) but we found a car was necessary to ensure that we could get around and eg buy groceries. There is a cash deposit required for check in, so it’s useful to withdraw that before you arrive. Our host was very responsive and helpful throughout our stay. Overall, we had a lovely time!

My fiance and I loved our stay here. beautiful views and prestige grounds. there were also a few friendly cats which made my fiancé's day. You need a car when staying here. you can find good restaurants and a grocery store a few minutes away in San casciano. It's centrally located in tuscany. 30 minutes to florence, 45 mins to siena. With lots of historic towns and wineries close by. The apartment was well accommodated, clean, and we'll equipped for cooking. We did pick up a few extra necessities from the grocery store and found the shower a little small, but otherwise found the stay comfortable and relaxing. Would totally recommend to friends and come back.

Chiara and Giovanni’s place is absolutely stunning. The accommodation is rustic and comfy; however the real gem are the grounds. Their land is beautiful and the pool is really special. They were kind and helpful hosts, we would definitely recommend this property to anyone staying in the area. Thank you both

Incredible location and hosts! The house was immaculate and exactly as described. We really had the best time and made use of all of the recommended restaurants and towns to visit nearby. We had an incredible trip and could not be more thankful to such kind hosts that made sure we had everything we needed and more.

Based on the previous wonderful reviews of Antiqua degli D’ulivi, a year ago we booked a three week stay in the outskirts of Cortona in Pergo. We had our kids, grandkids and dear friends with us and as we drove through the gates into the Villa, we entered a magical place filled with generosity, laughter, relaxation, wonderful food, a refreshing pool and golden light. Massi was always there to help us with any questions we had and refill our olive oil bottle with the amazing green liquid made from his olives. We enjoyed the most delicious lunch with his family and they also were such giving, lovely people. We learned so much about Italy and Tuscany from them: porcini mushrooms, Perugia soccer teams, local markets, hot springs near Montepulciano, nearby restaurants, vineyards, hikes and more. We highly recommend an extended stay at this Tuscan home—we were so fortunate to experience it for three glorious weeks. The memories will be long lasting and always treasured. Mille Grazie to Massi

We had a wonderful stay and Rita is a fantastic host. Beautiful and accommodating! Would recommend - only 10 min outside city center.

We (7 girlfriends) enjoyed the stay in the villa very much! The house, especially the front yard and pool, are wonderful. Maria is great! She has sent us a lot of tips about the area (also the necessary things, such as shopping). In addition, we were surprised with a very fine cake and if you needed anything, there was a very quick response. The villa is well equipped and the surroundings beautiful. Parking has enough. Only the potholes and the access to the villa are a bit challenging - but doable!

A paradise! Difficult access that is rewarded. A fantastic villa with spectacular views of the Tuscan hills. Greatly restored with modern and classic parts, plus an absolute calm, all around beautiful nature. A highlight: The spacious indoor Jacuzzi, we had a wonderful week, thank you!!

The place I stayed at this time was really artistic and beautiful. Thanks to the carefully placed objects and the unique interior, I felt like I was staying in a small gallery. From the natural light coming in through the window, to the colors that go well with it, to the quiet and cozy atmosphere — I was satisfied with everything. In particular, the details filled with the sensibility of the accommodation were impressive, so every moment felt special throughout my stay. This is a place I'd like to recommend to those who want to escape from everyday life and heal in an artistic atmosphere.

Stunning home in the middle of a lovely vineyard (Probably one of the best homes on AirBnB). It's even more beautiful in person - full of art, thoughtful design/luxury finishes, and Tuscan charm. Highly reccomend!!

Giovanna was such a wonderful host. It felt like a home away from home, with special touches added such as some food and wine in the apartment on arrival, and even a farewell drink before we left. The cottage is in breathtaking surroundings and in a perfect location to get around and explore different parts of Tuscany (with a car). I would highly recommend to anyone visiting the area ! We hope we can go back again one day!! Thank you Giovanna and Luigi !!