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Villa vacation rentals in Cortona

Find and book unique villas on Airbnb

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Popular amenities for Cortona villa rentals

Private villa rentals

Superhost
Villa in Chiusi
4.67 out of 5 average rating, 3 reviews

Tuscany 2 Villas sleeps 12 private heated pool

PiotrRating, 5 stars45 months ago
In reality villas present themselves a lot prettier than in photos on website. The area and surroundings are beautiful, calm and quite. Place is perfect as exit basis for exploring and sightseeing Tuscany. Rooms and beds are adequately big and clean. Kitchen and utensils are in sufficient quantity. Pool is clean, water warm. There’s no need for a battle for lawn chairs. Jacopo is very helpfull, communicative, serves his help everyday. The place is worthy of recommendation. We spent our holiday time comfortably in quaint area. All the best!
Guest favorite
Villa in Umbertide
4.92 out of 5 average rating, 12 reviews

Villa Comunaglia - Design Villa with Private Pool

SebastianRating, 5 stars8 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.
Guest favorite
Villa in Cortona
5 out of 5 average rating, 6 reviews

Villa Pietrenta

RandallRating, 5 stars8 months ago
This is a very comfortable house with beautiful views and a terrific pool. The house really consists of two apartments which works great when traveling with family. The living spaces are not large but work well- we spent most of our time outside anyway. About a 35-40 minute walk into the center of town. Parking in Cortona is tricky, so it’s nice to have the option to walk. Overall, a very good value, comfortable, well-maintained, and easy to use as a hub getting around the small villages of Tuscany and Umbria.
Top guest favorite
Villa in Gaiole in Chianti
5 out of 5 average rating, 20 reviews

Montemarcoli

RobertRating, 5 stars3 weeks 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 favorite
Villa in Toscana
4.88 out of 5 average rating, 60 reviews

Chianti Villa at Mulino del Cerchiaio

MathildeRating, 5 stars7 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 favorite
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 stars5 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!
Superhost
Villa in Provincia di Arezzo
4.91 out of 5 average rating, 43 reviews

Villa near Florence: Pool, AC, Vast natural garden

JackRating, 5 stars8 months ago
Stunning villa in a beautiful setting. Francesco gave excellent directions & the peace & tranquility out in the Tuscan countryside was wonderful. Francesco was exceptionally responsive & gave great local advice. We loved the little towns nearby and can’t wait to return soon. Highly recommended. Jack.

Luxury villa rentals

Guest favorite
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 favorite
Villa in Colombella
5 out of 5 average rating, 91 reviews

Torre Villa Belvedere Luxury & Relax with pool

VadimRating, 5 stars4 months ago
Well - I dont know where to start Basics - place is amazing. House, area, facilities, everything inside - by far the best airbnb we have been to and we will come back with friends again! You can't go wrong with this place and rating of 5 does not make justice- it should be 10 Now - this is all is nothing compared to how amazing hosts are - - i have never seen such hospitality and care before. We had a very difficult personal situation with my mom ending in the hospital and my wife getting very sick. Lavinia, Lorenzo and family were SOOOO helpful - they helped with EVERYTHING - there are real angels who helped us get through this very difficult time. I thank them all and pls come and stay here - region is great, place is second to none and hosts are just nicest people you will meet!
Top guest favorite
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 favorite
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 Paciano
5 out of 5 average rating, 4 reviews

Villa Lidia, la Dolce Vita at its Best!

IsaRating, 5 stars7 months ago
From the beginning, Marlene was an excellent host and Stijn, a most excellent property mgr. The house is even more beautiful in person. This is a magical place for tranquility and relaxation. The house is pristine and has all the amenities , we immediately felt right at home. We asked and they recommended farm to table cooking classes, and nearby towns to visit. All excellent experiences. Wonderful memories were made cooking and grilling, picking herbs from the garden. We enjoyed this truly spectacular home. The views from the hilltop where the house is located are breathtaking. There is a beautiful infinity pool and a great barbecue area. Watching sunsets and star gazing . We had just celebrated our daughter’s wedding and traveled from Rome and the serenity and Zen of the house and surroundings were just what we needed. Stijn took great care of us. We will return to this slice of heaven on earth. Thank you Marlene for sharing your beautiful home with us. It exceeded our expectation
Superhost
Villa in Torrita di Siena
5 out of 5 average rating, 4 reviews

Villa Scianellone

NickRating, 5 stars36 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 favorite
Villa in Cavriglia
4.99 out of 5 average rating, 128 reviews

Villa Poggio in Mandria in Chianti

EmilyRating, 5 stars6 months ago
We spent a week at Villa Poggio a Mandria as part of a group of six adults and had the most incredible and magical time. The photos do not do justice to how extraordinary the villa and surrounding area are — it’s nestled in an olive grove near the top of a hill just a short walk from a medieval village (Montegonzi), with utterly spectacular views in every direction. It could not be more peaceful or breathtaking. The villa was spotless, gorgeous and fully equipped, with tons of space for everyone. We had an unforgettable day with Lorenzo (contact available through Claudia and Leonardo), a local tour guide and chef who took us on an amazing wine tour and then cooked us the best meal ever that evening. And Claudia and Leonardo are the kindest, most responsive hosts, always available to answer any questions we had and even baking us a beautiful cake one evening! We can’t recommend Villa Poggio a Mandria enough. We had an unforgettable trip that truly felt like a dream. Thank you!
Top guest favorite
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.

Villa rentals with a pool

Superhost
Villa in Campagnatico
4.8 out of 5 average rating, 5 reviews

Charming villa on two levels - Casa Lola

SofiaRating, 5 stars9 months ago
Mel is a fantastic host and the place is exactly like in your most vivid Tuscany dreams.:) It's not our first time here and we absolutely loved everything about the place. We booked all three homes available at Mel's place and had an unforgettable week with the entire family - highly highly recommended! Thank you, Mel for being absolutely fabulous!✨
Guest favorite
Villa in Montepulciano
4.91 out of 5 average rating, 122 reviews

Villa in Montepulciano with a Pool

LindaRating, 5 stars2 weeks 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!
Guest favorite
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!
Villa in Gualdo Cattaneo
5 out of 5 average rating, 3 reviews

Villamari: Exclusive Villa, pool, panoramic view, Wi-Fi

CecilieRating, 5 stars33 months ago
Mario and his daughter Francesca are wonderful hosts with the most amazing property in Umbra! We were a big group of 18 friends, and Villa Mari was the perfect place for us because it is comfortable, stunning and has the fasilities for a big group who wants independency. Mario was easily in reach at any time if we had any problems. The property lies besides two other houses, but it feels very private and like you are all alone on the hill side. I cannot describe how beautiful the nature is, and the villa is also even better than in the pictures. Thank you very, very much Mario and Francesca! We hope to see you again:-)
Superhost
Villa in Greve in Chianti
4.83 out of 5 average rating, 29 reviews

Romantic Villa with private pool and fabulous view

RobertRating, 5 stars6 days ago
We absolutely enjoyed our stay. It felt like home from day one. The views are phenomenal; the garden is peaceful and fragrant. The kitchen is a delight to cook in. We walked into the beautiful village of Panzano multiple times (some hills which helped us burn off the pasta calories!). We didn’t want to leave.
Guest favorite
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.
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.
Top guest favorite
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