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Villa holiday rentals in Cortona

Find and book unique villas on Airbnb

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Popular amenities for Cortona villa rentals

Private villa rentals

Guest favourite
Villa in Umbertide
4.92 out of 5 average rating, 12 reviews

Villa Comunaglia - Design Villa with Private Pool

SebastianRating, 5 stars7 months ago
Andrea is a great host. The stay was amaizing and the support received from Andrea during stay was priceless. The place is wonderfull with great view and outstanding privacy. I will recommend Andrea as a host and his place as great choice for holidays.
Superhost
Villa in Chiusi
4.88 out of 5 average rating, 8 reviews

Villa Febea - Villa Febea 16

YonitRating, 5 stars21 months ago
Nestled in a stunning landscape, the villa is a marvelous retreat that captivates with its beauty and generous space. Meticulously maintained to uphold high standards, the villa's kitchen is thoughtfully equipped with all the essentials for a comfortable stay. Furthermore, each room is fitted with its own shower and toilet, ensuring privacy and convenience for all guests. The pool adds an extra touch of wonder to the experience. As for the hosts, Alice and Jacopo, they are simply delightful, providing warm hospitality throughout your stay. I wholeheartedly recommend this exceptional villa for an unforgettable getaway
Top Guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 20 reviews

Montemarcoli

RobertRating, 5 stars1 week ago
Our stay at Villa Montemarcoli was fantastic. So peaceful. No noice from cars and really no air traffic noise whatsoever. Just the birds singing. Just want to mention you will need to drive to everything but the roads are so beautiful you won’t mind! I would recommend a small SUV or car with all wheel drive as the villa is located up a gravel road and roads in the area can be narrow and parking can be tight in places. I would definitely recommend Brigitta’s Villa and hope to come back again someday 😎🍷
Guest favourite
Villa in Reggello
4.87 out of 5 average rating, 30 reviews

Villa Arianna, your villa in Tuscany

JulianaRating, 5 stars6 months ago
Oscar was very friendly and kind to us! His house is beautiful and comfortable, we were in a group of 13 people and we were peacefully hosted. Beautiful decorations and landscapes. 10-star rating.
Guest favourite
Villa in Toscana
4.88 out of 5 average rating, 60 reviews

Chianti Villa at Mulino del Cerchiaio

MathildeRating, 5 stars6 months ago
Thank you!! We enjoyed our vacation with 9 friends! A little humid because of the weather, but the place is ideal in summer and comforting by the fire when the good weather is not present!
Guest favourite
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio in the Tuscan countryside

LizRating, 5 stars7 months ago
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!!
Superhost
Villa in Montepulciano
5 out of 5 average rating, 3 reviews

Terra Antica Suites & Villas - Villa Vino - Private Jacuzzi

HeatherRating, 5 stars4 months ago
Our stay at Terra Antica was a dream. The location is perfect and the property and villa are exceptional. We were close enough to town to get to restaurants and shopping and then come back for some quiet relaxing time. There are numerous wineries to visit in the area. Day trips to other local towns are easy to do as well. The private jacuzzi was an extra bonus & we used it several times during our stay. We will be back again!
Top Guest favourite
Villa in Paciano
4.97 out of 5 average rating, 39 reviews

Villa Fortuna with Hot-Tub and pool near Tuscany

AndrewRating, 5 stars6 months ago
We stayed here for 4 weeks and it really felt like home. The house is wonderful, kitchen has everything you need for cooking in, bedrooms are comfortable, small laundry room, and you can tell the house has been really well cared for. The outdoor area is spacious and private. We were there in Autumn so the hot tub was open, really beautiful at night. The front yard overlooks the lake, beautiful views everywhere you look. Finally, the house is just 5 minutes from lovely Paciano and only 20 from several other larger towns, and you don’t need to go far to find great food and things to do.

Luxury villa rentals

Guest favourite
Villa in Sodo
4.95 out of 5 average rating, 22 reviews

The House of the Sole del Sodo

ClaireRating, 5 stars7 months ago
We chose Il Sole del Sodo because it had 6 en-suite rooms, a pool, was close to a town and a train station and had a well- regarded host who could provide extras like breakfast, dinners, cooking classes and olive oil tastings e.g. Claudia! While rustic, the villa’s charm and peaceful spaces draw you right in and Claudia’s hospitality is unsurpassed. The villa fronts to the road to Cortona and backs to a field of sunflowers. Our family and friends dined on the private patio and found a back way to walk up to Cortona for exercise. A unique and wonderful experience!
Guest favourite
Villa in Montepulciano
4.91 out of 5 average rating, 121 reviews

Villa in Montepulciano with a Pool

LindaRating, 5 stars1 week ago
We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!
Top Guest favourite
Villa in Montone
4.94 out of 5 average rating, 17 reviews

Villa San Lorenzo | Private Pool, AC & Jacuzzi

JacquelineRating, 5 stars6 months ago
The house was great with amazing countryside views. The rooms and common areas were spacious. Our favorite spot was the enclosed patio dining area where we had breakfast every morning overlooking the rolling hills. The hosts were great, very responsive and helpful.. One of the hairdryers was not working but Maurizio got us 2 new ones in no time. He also gave us recommendations for restaurants. Awesome hosts!
Guest favourite
Villa in Passignano sul Trasimeno
4.9 out of 5 average rating, 30 reviews

Villa with panoramic pool • Lake Trasimeno

DonRating, 5 stars7 months ago
Thank you Paola for a wonderful week in you family Villa . The views are amazing and the house felt like home. Great place to stay with our family of 8 adults and a baby.
Superhost
Villa in San Leo Bastia
4.92 out of 5 average rating, 12 reviews

Villa Elisa | Private Pool, Air/Co & Amazing View

Carlos Rating, 5 stars6 months ago
Villa Elisa is the best place I have stayed so far. Its construction style is old and special, the care of the Villa is down to the details, whether it is the exterior or interior, everything works is impressive even though some parts of the house are original from that time such as the doors, the windows, the floor tiles,The view is magnificent, magical whether with the radiant sun, under a torrential rain, under the clouds, under the mist or under the stars with the moon as a companion.Absolutely everything in detail and scrupulously organized, all thanks to its hosts Luciano and Christina. Now I will make an important section, if the Villa is majestic, they are also splendid and kind; I had the pleasure and pride of meeting them personally, people like few I have ever met and who are now scarce. Natural, simple and kind, always at hand unconditionally for whatever was needed.I recommend this place to everyone who wants to enjoy a great place and excellent company and 100 percent.
Superhost
Villa in Torrita di Siena
5 out of 5 average rating, 4 reviews

Villa Scianellone

NickRating, 5 stars35 months ago
We had an excellent time staying at this family home with an amazing view of Torrita di Siena. Great access to many popular hill towns (Cortona, Montepulciano, Pienza, Montalcino, etc). The house and property are beautiful, very private and populated with song birds and olive trees. The hosts are charming and very welcoming. They provided us with all the recommendations we needed and were readily available whenever we wanted to communicate with them. The house is well appointed and has multiple ways to cook from gas range to pizza oven and wood fired grill. I really liked using the giant pinecones as fire starter. We would definitely return and hope to. Such a precious slice of paradise.
Top Guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 47 reviews

Sestuccia

RebeccaRating, 5 stars6 months ago
We had a marvelous stay at Villa Sestuccia. The house is spacious, as are the grounds. Both are well maintained. There is ample room with different areas to relax indoors and outside. We communicated with Briggita who was quick to respond, always friendly and always helpful. We particularly liked the location which has easy access to many spots of interest and restaurants. We enjoyed collecting eggs in the morning for our breakfast - such a fun touch. We highly recommend Villa Sestuccia and would not hesitate to stay here again.
Superhost
Villa in Pierle
4.88 out of 5 average rating, 26 reviews

Historic Villa Getaway with 6BR/9BA, Pool, Views

GeoffRating, 5 stars6 months ago
This place is a must see! Great for large groups, if you book this villa you MUST ask about having Gimmi the sommelier come out for a meal and wine pairings, it was the highlight of our entire trip.

Villa rentals with a pool

Villa in Marciano
5 out of 5 average rating, 7 reviews

Villa Signana with pool for 20+ people by LLL

DmitriRating, 5 stars7 months ago
We rented Jacopo’s place with 17 people for anniversary and had an outstanding time! He stopped by frequently to check on us and give local recommendations. The villa is amazing. So good we were considering buying it!
Top Guest favourite
Villa in Località Poggio Olivo
4.98 out of 5 average rating, 57 reviews

Beautiful villa with swimming pool in Tuscany

RoccoRating, 5 stars6 months ago
Our stay at the villa was absolutely incredible! The property (villa, surrounding grounds and the pool area) and the view were beautiful. The photos do not do it justice. it is exactly what you envision when thinking of a Tuscan villa. The house is large and clean, and it easily accommodated five adults with lots of extra room. The location is also very convenient, being close to a large grocery store and to the A1 highway. There are many restaurants and wineries nearby as well. Marco was a fantastic host who was very communicative and responsive. His parents (Ario and Santina), who live nearby, were lovely and friendly, while also giving us our space and privacy. Thank you very much Marco, Ario and Santina!!! We were sad to leave your beautiful villa and hope to be back soon!!
Guest favourite
Villa in Castiglion Fiorentino
4.95 out of 5 average rating, 39 reviews

Villa Il Sogno di Pietro, private pool and AC

SheebaniRating, 5 stars7 months ago
We loved our stay at this beautiful place! It was extremely peaceful and our family had a great time!
Superhost
Villa in Greve in Chianti
4.82 out of 5 average rating, 28 reviews

Romantic Villa with private pool and fabulous view

MenkoRating, 5 stars7 months ago
This an absolutely wonderful house with so many qualities inside as well as outside. Extremely well decorated and dreamy wonderful house inside, superb and beautiful views outside in a big and calming garden. Janine is fantastic, super friendly and extremely helpful. We forgot our passport and it was brought to Florence. This is just one example. Nothing to add, amazing to stay here.
Guest favourite
Villa in Monte San Savino
4.99 out of 5 average rating, 69 reviews

CHARMING TUSCANY VILLA PRIVATE POOL

Tsz Kwan CarrieRating, 5 stars6 months ago
Francesco is nice:) He brought us welcome pizzas and dessert. His response is instant. The place is quiet which provide you completely private place. Just a bit far from town if you cannot drive yourselves. If you have cars, it is not a problem, just few minutes drive from town. The place looks exactly the same as the pictures, clean and tidy. Definitely enough space for 8 adults. Recommend.
Villa in Castiglione del Lago
4.78 out of 5 average rating, 9 reviews

A Beautiful Original Villa

RobertRating, 5 stars8 months ago
We really enjoyed our one week family holiday staying in this villa. The house, garden and pool are as described and absolutely gorgeous! The weather was extremely hot so we particularly appreciated the beautiful pool as well as the possibility to eat outside in the well shaded area overlooking the pool. Also, there is a plentiful supply of tableware for outdoor use which is very practical. The location was ideal for visiting destinations such as Assisi and Montepulciano, but it was also great just taking it easy and enjoying the garden, pool and views. The villa is 10 mins by car from CDL although the last part is on unmade roads which can be quite bumpy. We found Google Maps worked best for navigating to/from the villa but led us astray on occasions - Beware! Alessandra was a great host. She was there to welcome us on arrival and explain everything we needed to know. Throughout our stay she was very responsive to our questions and recommendation requests. We recommend this villa!
Superhost
Villa in Provincia di Siena
4.76 out of 5 average rating, 29 reviews

Villa Limone - 3 bedroom villa in Tuscany

MeirRating, 5 stars6 months ago
Amazing place Our only regret is that we didn't stay loner
Top Guest favourite
Villa in Ortignano Raggiolo
4.94 out of 5 average rating, 69 reviews

Private Villa with swimming pool in Tuscany

TomášRating, 5 stars6 months ago
We had a wonderful stay at the villa in Tuscany and felt at home right away. The hosts, Silvana, Iacoppo, and Bruno, took excellent care of us and were always attentive to our needs. The villa itself is spacious and well-equipped with everything one could ask for. The beautiful pool with its stunning views and the cozy fireplace area were definite highlights. It was the perfect place to unwind and enjoy the Tuscan countryside. Thank you again for an unforgettable stay!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Arezzo
  5. Cortona
  6. Villa rentals