House vacation rentals in Cortona

We spent a week here- half for work and half for leisure. Traveling with two children under 6 can sometimes feel challenging but we immediately felt at home at Rosella’s. The beautiful home greeted us with a welcome basket full of coffee and goodies- the pool was devine and the bedding was really really comfortable. We have already recommended this listing to a few friend and we would welcome the chance to come back. Thank you for a wonderful stay.

What a wonderful stay. Perfect house for a family holiday with plenty of space for everyone. The house is beautiful and the beds all king size and comfy. The outdoor space and pool are perfect for relaxing after exploring the local area. Within easy reach of exploring the Tuscan gems of Siena and Montipluciano as well as lesser known villages such as spectacular Montone. Alessandro was so responsive and helpful providing recommendations for wine tours and a local chef. The local restaurant Mimmi is not to be missed - authentic home cooked food that was one of the best meals we ate - and the bar was set high. Thank you Alessandro for a wonderful and memorable stay.

We stayed 5 amazing days at Il Gufo and loved every minute. Jacopo is an amazing host and went out of his way throughout to make our stay great. Even meeting us locally and showing us the way to the house. We highly recommend staying at The Owl. The location, high in a valley provides spectacular views and is perfect to relax and unwind. We do not know what was better. The location, accommodations or the fact that we met Jacopo and became immediate friends. That combination made for the greatest memories. Also Luba, their beautiful dog, immediately loved us and greeted us ever time we returned. A little secret, he is an amazing chef and if you get a chance to go to his restaurant do it. Also his dinner recommendations were great. We had dinner at Corte Dei Frati 2 times. Thank you Jacopo for making our 30th Anniversary trip so amazing. We feel privileged to have met you and we will return on our next trip to Italy. You are an amazing person and host. Love Steve & Vicki

This home is the epitome of a classic villa in the chianti region. Lecchi is very a small village that is walkable to a market, bar & cafe, and one of the best dinner spots we visited in our entire trip to Italy - the Malborghetto restaurant is a must! We rented a car for this week of our trip, and would highly recommend doing so. There are many nearby villages with great trattorias and shopping options - and gorgeous views everywhere you turn. Casa di Lyndall is a roomy, well appointed home with all the amenities you could need. Very clean, and very comfortable, and the view out the front windows is beyond compare. Lyndall was very responsive and provided us with excellent recommendations of things to do during our stay. Clementina greeted us when we arrived and was so sweet and helpful. There is nothing we would change about our stay!

Our group of ten absolutely loved staying at Nella's house this June. Nella was good at communicating and set us up in advance with a local driver and for the local chef to come up and cook for us one evening. When we arrived the house was in perfect condition and we quickly felt right at home. The house has a gorgeous view of the sunset in the evening and we were perfectly located to be able to walk into Cortona. Thank you Nella!

Norma was an absolute treasure, and her home and family were lovely. The property sits overlooking a lovely castle and a beautiful church with great views on the other side. The property has a great pool with plenty of privacy or interaction with the family, I only wish I spoke more Italian to be able to sit and chat with her lovely in-laws! Norma offered great recommendations for day trips, and overall the local area was great to explore. My only advice would be the usual: rent a smaller car to make life easier! Sitting on the patio overlooking the castle, with a glass of wine, is a memory we will never forget, and is highly recommended. Whether during the day or after the sun has gone down and the fireflies comes out (weather permitting) it's a Tuscan treat you won't want to miss. We truly felt like a part of the family and would love to return to her home the next time we come back. Truly a wonderful experience!

We had an awesome time at Lucy's and Tommy's, the house was spacious and beautifully decorated. The garden and surroundings are amazing, very peaceful and inspiring. Lucy and Tommy are great hosts who provided very helpful recommendations for off-the-beaten-track activities.

Always in love with Cortona, we spent 4 days in Giovanni's farmhouse, a stone's throw from the historic center and in a position that allowed us to enjoy the views and tranquility of the Tuscan countryside. The farmhouse is carefully renovated and perfectly matches the photos. They were greeted with kindness and we appreciated the flexibility and the small details (a bottle of fresh water, the oil produced in-house, the things that make you feel at home). The pool is definitely the highlight of a farmhouse that makes you feel perfectly immersed in nature and the authentic spirit of Tuscany. Everything is wonderful!

first I love his neighbors who checked us in. Cinzia was amazing. She not only showed us our place but took our kids to show us her farm. she also makes her own olive oil and gifted us with some! Wonderful Italian neighbors!! I contacted Rocky in advance and he provided me with specific recommendations for where we should go during a long drive we took. we went where he suggested and was not disappointed! Amazing quiet location with great near by wineries. would 100% recommend to everyone!

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!

Franco is very welcoming, the apartment is a beautiful renovation equipped with every comfort. Highly recommended! Luca and Noélie

Sarah was in touch with us before arrival, recommended restaurants and inform us about the parking place, as you can't park inside the old town. the apartment was as in the pictures, beautiful view

To value this property, you have to start with the HOST, a professional in every sense. From the minute 0 of the reservation, until check-out; always attentive, very friendly and very professional. It's a pleasure to meet serious people and this gives the app value. The beach house is a paradise in Italy. Easy access, attention to detail, peace, nature, comfort. Our trip was as a family with our two poodles and I think they were the ones who enjoyed the property the most, seeing them run and jump through the green areas of the property and live with many birds, rabbits is priceless. Our daughter enjoyed her stay studying and with the peace and quiet of the place, it was easy for her to concentrate. We, on the other hand, did some sightseeing in the area, everything is very close and well connected by road. It is a very well-kept, safe property and above all, enjoying its sunset, sitting on a lounger, enjoying a good wine (from the area) is an unrepeatable experience. Thank you Maurizio.

We stayed 4 days and it was just fantastic. The arrival was hassle-free and Flavia welcomed us very warmly on site. After a short tour of the house and a short briefing, the holiday could begin. A note with restaurant recommendations and excursion destinations was ready on the table. After a short thunderstorm, we had a power outage, but Flavia was immediately available and within 5 minutes we had electricity again. Shopping and restaurants are easily accessible by car. I would recommend this place to anyone who longs for peace and wants to enjoy nature. We will be happy to come back!

We had a wonderful week-long visit. I wish we had stayed longer. The villa is beautiful. It is spacious, clean, with modern amenities and appliances but also has some very nice antique furniture and decor. The outdoor patio is really amazing, with views of distant Tuscan hills and farms, olive and cypress trees - a great place to eat and relax outdoors. Nearby Arezzo is a great place to visit. There are many interested museums, churches and places to visit in the older section of the town (including the Basilica di San Francesco with frescoes by Piero della Francesca), but there are also more modern parts of town with shops and restaurants, and ample parking. The villa is also within easy driving distance of many other surrounding towns (such as Cortona) and places to visit. Our hosts were super helpful and friendly, and we especially enjoyed the olive oil that is provided and made from the trees growing on the property. We would definitely stay here again.

Beautiful home in a more secluded area overlooking Lake Trasimeno. The trains and a highway are below but not invasive. The views are beautiful. The home was clean and tastefully updated but still clearly old and had a lot of character. We did not have a car and the train station is an hour walk away. There are a couple buses that pass through but not enough to be a reliable means of getting to and from the house. Even the taxi was busy and we had to be flexible on when we went to the train station but it worked out fine. We walked to and from Tuoro for groceries and visited La Puntabella for a great dinner with a view. It was an adventure and we enjoyed it despite our plan not being very good for this location. Sonia was patient and helpful in working out our means of travel and figuring out the bus schedule. Natolino reminded us of home and he is fun to watch and listen to.

We spent two weeks at Rolando and Patrizia's with our two one-year-old and three-year-old children. The place is absolutely beautiful with a sublime view. They had a lot of little touches for our children throughout the stay. It was always a pleasure to chat with them. Accommodating, very considerate. The kids were always happy to see them. As for the house, it is very nice and easy to live in. The two terraces are a real plus. And again the views filled us throughout our stay.

Amazing place and would definitely be our number one place to stay when we return. Clean and spotless with luxuries like slippers are provided and some breakfast items too. Even a UK-Italy plug converter! Loved it! Thank you to Lucia, Luca and your mum! xx

The stay "Casa Elisa" was better than we expected. It is a large house with even a basement with sauna. The pool in the garden (with outdoor shower and toilet) and the house itself were sparkling clean. There was no dust or cobweb to be discovered (not even behind a closet that we moved to be able to reach an outlet). The view from the balcony was breathtaking and the surroundings were fantastic. You are so in towns such as Siena, Arezzo, Perugia and there is also a large lake nearby where we rented a boat for a day (recommended). In short, we can recommend everyone to book with Lorenzo. The communication with Lorenzo was also excellent, easy to reach via app and speaks good English. His father comes to check and clean the pool every day and his mother's day baked a delicious cake very sweetly.

Paola was a lovely, gracious and attentive host. The location was perfect, with in a short drive to everything Cortona has to offer.. We enjoyed exploring the area and found plenty of great dining options nearby. Overall, our experience was nothing short of amazing. We cannot recommend Paola and her property highly enough. Thank you for a wonderful stay.

Suitable for those wanting a peaceful getaway in Tuscany which is close to Cortona and Castiglion Fiorentina. Great views over the valley to enjoy with public transport [ trains and buses] not far away to take you further afield. You do your own transport to get there as up a hill, which whilst walkable, but not with luggage. Modern kitchen, comfortable beds, good internet and a Smart TV ensure you don't miss your home comforts. But oh so peaceful!

Parking with great view was smooth. Since it is a house right near the entrance door of the city, transportation was very convenient. Everything was available in the house. We had a very peaceful and calming holiday. Thank you

We can’t say enough good about Paola’s place. It is absolutely beautiful and the location is so pretty. The scenery & sunsets are breathtaking. Paola is so very kind, always checking to make sure everything is to your liking. She had wonderful restaurant recommendations and even made our reservations for us which was very helpful. If you’re not good on your feet, the walk up to the main area of Montepulciano, is a bit of a hike up as well as from parking area just so you’re prepared. You’ll have everything you need at Paola’s as she has everything. You’ll be right at home. Make sure you go to the Fruit Cafe for coffee and any breakfast or snacks. The owner is such a nice man and his coffee and food are so good. The bed is comfy at Paola’s and the shower is nice and hot and lasts. It was one of our nicest stays. Thanks for everything Paola!!

Bianca is one of the best hosts I ever encountered. She is very friendly, welcoming and social. She is very passionate about her house and guests. She treated us like friends and I think we already became friends for life. Her house is very special, magical, clean and beautiful. Its very spacious felt right at home and had everything we needed. Its private and peaceful yet walking distance from Grassina town down the hill, around 10 minutes walk. The town has everything you need from restaurants to bars, Farmacia, little boutique shops and beauty salons. The location is perfect and outside the city but only 20-30 minutes from Florence. I am defiantly coming back to this place.