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House holiday rentals in Cortona

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Popular amenities for Cortona house rentals

House rentals with a pool

Top Guest favourite
Home in Castiglion Fiorentino
5 out of 5 average rating, 35 reviews

Hidden gem in Tuscany

MitchellRating, 5 stars3 weeks ago
Where to start? I truly can't say enough good things about this property. It exceeded expectations in every way. From start to finish, our time here was a delight. Amanda was responsive, helpful, and accommodating. The location is remote, and a bit of adventure to get to, but Amanda had communicated that and we were prepared with the proper rental car that made it a breeze. The house is beautifully appointed, has every amenity, and lots of perfect spaces for both quiet moments and areas to gather with your group. The outdoor spaces and pool area are lovely, beautifully landscaped, and the views are spectacular. Book this place; you won't be sorry.
Top Guest favourite
Home in Cortona
4.97 out of 5 average rating, 89 reviews

Traditional stone house in Tuscany

HannahRating, 5 stars2 weeks ago
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.
Superhost
Home in Figline Valdarno
4.96 out of 5 average rating, 107 reviews

The Owl: view, pool and garden

StephenRating, 5 stars1 month ago
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
Guest favourite
Home in Lecchi in Chianti
4.96 out of 5 average rating, 136 reviews

Casa di Lyndall - Entire house with exclusive pool

TerriRating, 5 stars7 months ago
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!
Guest favourite
Home in Cortona
4.91 out of 5 average rating, 43 reviews

Country charm walking distance from Cortona centre

MargaretRating, 5 stars1 week ago
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!
Top Guest favourite
Home in Subbiano
4.99 out of 5 average rating, 82 reviews

Romantic cosy flat - Toscana Italy

JoeRating, 5 stars1 week ago
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!
Guest favourite
Home in Cortona
4.93 out of 5 average rating, 29 reviews

Beautifully restored villa with private pool

GaëlRating, 5 stars1 month ago
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.
Guest favourite
Home in Cortona
4.92 out of 5 average rating, 13 reviews

[L'Antico Casale] Timeless Retreat in Cortona 5*

EmanueleRating, 5 stars1 week ago
Da sempre innamorati di Cortona, abbiamo passato 4 giorni nel casale di Giovanni, a due passi dal centro storico e in posizione che ci ha permesso di godere dei panorami e della tranquillità della campagna toscana. Il casale è ristrutturato con cura e corrisponde perfettamente alle foto. Siano stati accolti con gentilezza e abbiamo apprezzato la flessibilità e i piccoli dettagli (una bottiglia di acqua fresca, l'olio di produzione propria, le cose che ti fanno sentire a casa). La piscina è sicuramente il punto di forza di un casale che ti fa sentire perfettamente immerso nella natura e nello spirito autentico della Toscana. Tutto meraviglioso!

Weekly house rentals

Guest favourite
Home in Castelmuzio
4.98 out of 5 average rating, 40 reviews

Casa Ora d"Oro - Panoramic Views

Jason AllenRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Asciano
4.97 out of 5 average rating, 33 reviews

Family Forest - Piscina nelle Crete Senesi

SylviaRating, 5 stars1 week ago
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!
Guest favourite
Home in Arezzo
4.88 out of 5 average rating, 24 reviews

Colonial house immersed in a natural park.

MarieRating, 5 stars9 months ago
Nous avons passé deux semaines chez Rolando et Patrizia avec nos deux enfants d’un an et trois ans. L’endroit est absolument magnifique avec une vue sublime. Ils ont eu beaucoup de petites attention pour nos enfants tout au long du séjour. C’était toujours un plaisir de discuter avec eux. Arrangeants, très prévenants. Les enfants étaient toujours contents de les voir. Pour ce qui est de la maison, elle est très agréable et facile à vivre. Les deux terrasses sont un vrai plus. Et à nouveau les vues nous ont comblés tout au long de notre séjour.
Guest favourite
Home in Castiglion Fiorentino
4.94 out of 5 average rating, 81 reviews

La piccola torretta

LucaRating, 5 stars2 weeks ago
Franco è molto accogliente, l’appartamento è una bellissima ristrutturazione dotata di ogni comfort. Consigliatissimi! Luca e Noélie
Top Guest favourite
Home in Magione
5 out of 5 average rating, 19 reviews

Beach House, sulle rive del Lago Trasimeno

Juan DiegoRating, 5 stars1 week ago
Para valorar esta propiedad, hay que empezar por el ANFITRIÓN, un profesional en toda regla. Desde el minuto 0 de la reserva, hasta la salida; siempre atento, muy amable y muy profesional. Es un placer conocer gente seria y esto la da un valor a la aplicación. La beach house, es un paraíso en Italia. Fácil acceso, cuidado al detalle, paz, naturaleza, comodidad. Nuestro viaje era en familia con nuestros dos caniches y creo que fueron los que más disfrutaron de la propiedad, verlos correr y saltar por las zonas verdes de la propiedad y convivir con muchas aves, conejos no tiene precio. Nuestra hija disfrutó su estancia estudiando y con la paz y tranquilidad del lugar, no le costó nada concentrarse. Nosotros en cambio, hicimos turismo por la zona, todo muy cerca y bien comunicado por carretera. Es una propiedad muy cuidada, segura y sobretodo disfrutar de sus puesta de sol, sentado en una tumbona, disfrutando de un buen vino (de la zona) es una experiencia irrepetible. Gracias Maurizio.
Top Guest favourite
Home in Arezzo
5 out of 5 average rating, 12 reviews

Villa Medici Donnini Superior Apartment

RobertRating, 5 stars3 weeks ago
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.
Top Guest favourite
Home in Tuoro sul Trasimeno
5 out of 5 average rating, 53 reviews

l'oasi delle volpi

AbbyRating, 5 stars1 week ago
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.
Superhost
Home in Lucignano
4.85 out of 5 average rating, 39 reviews

La Casetta

LauraRating, 5 stars1 month ago
Beautiful, peaceful stay. Amazing, secluded location. The hosts were very friendly and welcoming - made us feel right at home. Lots of great walks around, including the nearby winery. The only downside is it does get rather cold in the stone apartment but during warmer weather the coolness in the apartment would probably be perfect. They provided a portable heater & a hot water bottle though which was nice. Thank you Tebea for being such a lovely host!

Private house rentals

Top Guest favourite
Home in Loc. Casalini - Comune Panicale
4.99 out of 5 average rating, 95 reviews

Casolare immerso nella natura

AlanRating, 5 stars4 days ago
Stayed here last week for 5 days. On arrival we were met with a welcome basket of food a bottle of wine a bottle of homemade olive oil and also bottles of water on arrival. The pictures don’t do it justice it felt like a place out of a fairytale, the property is surrounded by tons of olive trees and greenery. If you want a quiet relaxing holiday this is place to go. Rosella was amazing with quick responses and extremely welcoming, we are definitely going again next year.
Superhost
Home in Montepulciano
4.9 out of 5 average rating, 29 reviews

Agriturismo I Fuochi | Casa Susino

ClementineRating, 5 stars10 months ago
Nous avons passé 2 semaines très agréables dans cet agritourismo; la piscine est très grande, bien entretenue et la température parfaite! Les enfants ont appréciés les jeux prêtés. Le logement au rez de chaussée parfait pour une famille avec ses 2 chambres. La situation, au milieu des vignes et oliviers correspond à l’image que l’on se fait de la Toscane. Le calme dépendra des autres touristes qui partagent le logement….
Top Guest favourite
Home in Città della Pieve
4.97 out of 5 average rating, 75 reviews

La Terrazza di Vittoria

NickyRating, 5 stars1 month ago
Alessandro ist ein super netter Typ. Die Unterkunft ist einfach nur traumhaft schön. Der Ausblick ist einmalig und das kleine Haus ist sehr sauber und schön eingerichtet. Wir würden jeder Zeit wieder kommen. Es war einfach ein toller Urlaub und wir haben uns dort wie Zuhause gefühlt
Top Guest favourite
Home in Monticchiello
5 out of 5 average rating, 39 reviews

Graziosa abitazione per sognare

SarahRating, 5 stars1 week ago
Nous sommes tout de suite tombés sous le charme de l’appartement et nous nous sommes sentis comme chez nous pendant nos trois nuits là-bas. C’était exactement voire mieux que ce que nous avions imaginé. Merci Sara pour cet accueil incroyable! ♥️
Superhost
Home in San Leo Bastia
5 out of 5 average rating, 31 reviews

Hamlet of San Biagio a Colle - Casa del Prete

LilaRating, 5 stars10 months ago
Was lovely to stay at one of the apartments on Renato's estate. Renato and his wife are very kind and friendly and made us feel at home. The estate is very secluded on hilltop 5km drive from the village, with beautiful grounds providing enough privacy for individual apartments as well as a restful setting. Would love to go back next time we're in the area.
Top Guest favourite
Home in Montepulciano
4.95 out of 5 average rating, 19 reviews

Hortus Conclusus House

FionaRating, 5 stars2 weeks ago
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
Guest favourite
Home in Cortona
4.97 out of 5 average rating, 59 reviews

"Casa Elisa", casa con piscina ai piedi di Cortona

DanielleRating, 5 stars1 month ago
Het verblijf 'Casa Elisa' was beter dan we hadden verwacht. Het is een groot huis met zelfs een kelder met sauna. Het zwembad in de tuin (met buitendouche en toilet) en het huis zelf waren brandschoon. Er was geen stofje of spinnenweb te ontdekken (zelfs niet achter een kast die wij verschoven om bij een stopcontact te kunnen). Het uitzicht vanaf het balkon was adembenemend en de omgeving was fantastisch. Je bent zo in plaatsjes zoals Siena, Arezzo, Perugia en er is vlakbij ook een groot meer waar wij een dag een bootje hebben gehuurd (aanrader). Kortom, we kunnen het iedereen aanraden om bij Lorenzo te boeken. De communicatie met Lorenzo was ook uitstekend, goed te bereiken via app en spreekt goed Engels. Zijn vader komt elke dag even het zwembad checken en schoonmaken en zijn moederdag heel lief een heerlijke taart gebakken.
Top Guest favourite
Home in Arezzo
5 out of 5 average rating, 13 reviews

Santa Flora Home • Swimming pool • Gym

DanielRating, 5 stars1 month ago
Letizia and Virginia were absolutely great! The place is much bigger than we expected. Letizia takes great care of the garden and was prompt to respond. Virginia gave us great tips of places to visit. Would definitely recommend.

Destinations to explore

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