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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

AnneRating, 5 stars8 months ago
Superbe emplacement en hauteur de la campagne et des collines d’Ombrie. Vues magnifiques depuis la maison et le jardin. Équipement parfait et les 2 maisons permettent de séparer les adultes des plus jeunes ce qui a participé au déroulement très agréable des vacances familiales.
Guest favorite
Villa in Orvieto
4.9 out of 5 average rating, 31 reviews

Villa spettacolare panorama ed infinity pool

JokeRating, 5 stars8 months ago
De villa is prachtig gelegen op een heuvel met een adembenemend uitzicht. Hij is heel mooi en luxueus ingericht De 6 slaapkamers zijn erg ruim en elk voorzien van een douche. Enkel de uitrusting van de keuken mocht wat beter. Zo werkte de vaatwasser niet naar behoren en was de BBQ oud en versleten. Maar dat zijn dan ook de enige minpunten. Ook het terras is heel ruim en volledig overkapt wat de nodige bescherming biedt op warme dagen. Er waren 2 lounge sets en 2 grote tafels aanwezig. Het zwembad werd regelmatig gereinigd. Dat gebeurde 's morgens vroeg zodat we daar geen last van hadden. Er waren voldoende ligbedden en parasols alsook handdoeken aanwezig.
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.
Guest favorite
Villa in Pian di SCO
5 out of 5 average rating, 26 reviews

Villa il Palagio nelle campagne toscane

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 Suite & Ville - 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.
Top guest favorite
Villa in Todi
4.99 out of 5 average rating, 97 reviews

Villa in Todi with Pool CIN: IT054052C21M032265

MaryaRating, 5 stars6 months ago
Bellissima! This spacious Italian villa in the lush Umbrian Hills is part of an olive estate owned by the gracious hosts, Claudia and Alessandro. It has a magnificent view of the countryside and the distant hills, including the charming medieval hilltop town of Todi. The region is lush and green and even in October is perfumed with the scent of wild mint, lavender, rosemary and thyme. The beds and linens were very comfortable and the kitchen was the best stocked I have ever seen in a vacation rental (even with a teapot, bless you!) We were lucky to stay there during the olive harvest and were able to buy some delicious olive oil straight off the press. Grazie mille per tutto, Claudia and Alessandro; we will think of Passo della Polomba while we enjoy our olive oil back in Canada! Arrivederci e alla prossima!

Luxury villa rentals

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

La Casa del 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!
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 con piscina panoramica • Lago Trasimeno

LaurentRating, 5 stars9 months ago
Très très belle maison pleine de charme avec une superbe vue sur le lac. Hôtes très réactifs et proposant de nombreuses options bien appréciable. Au plaisir d’y revenir un jour !
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.
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 a 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!✨
Top guest favorite
Villa in La Cima
4.93 out of 5 average rating, 30 reviews

Lake View Country Villa w Pool

YedongRating, 5 stars6 months ago
A short while ago, we (4 adults of the same family) stayed in this house. It is located nearby lake Trashmeno and you can have a great view from the house. The traditional house is surrounded with a beautiful garden with a private swimming pool. The house is specious, a big living room and a well equipped kitchen. It is clean. Above all, The hosts Sheetal and Vittorio are super helpful. They waited us at the door steps, gave us all the detailed information about What to do, Where to eat & drink, supermarket, etc. and also helped us to make a restaurant reservation. They responded to our questions throughout with detailed information and links. They are the best hosts to us. Sheetal and Vittorio, many thanks. If we could, we'd like to spend our holiday here again. It is highly recommended.
Guest favorite
Villa in Montepulciano
4.91 out of 5 average rating, 122 reviews

Villa a Montepulciano con Piscina

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, piscina privata e AC

ChanitahRating, 5 stars7 months ago
Het huis was prachtig. Bijna alles was geweldig een paar kleine puntjes. De keuken wat klein voor een grote groep. Er miste schaaltjes voor bijvoorbeeld yoghurt… of die hebben wij niet gevonden. Er was een stopcontact in een slaapkamer wat onveilig en er miste een douchegordijn in de gedeelde badkamer. Maar verder was het geweldig alles heel schoon en groot prachtige zwembad met tuin eromheen. Erg genoten
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.
Guest favorite
Villa in Toscana
4.88 out of 5 average rating, 60 reviews

Chianti Villa Mulino del Cerchiaio

MathildeRating, 5 stars7 months ago
Merci !! Nous avons bien profité de nos vacances entre copines à 9 ! Un peu d’humidité du fait du temps, mais l’endroit est idéal en été et réconfortant au coin du feu quand le beau temps n’est pas présent !
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