Cortona Vacation Rentals

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Browse Select Cortona Vacation Homes

Indoor pool, outdoor pool
Private Pool & Cottage for 6 in Secluded Hamlet Spectacular Views 7 km to Corton
10.0 out of 10, Exceptional, (8)
"We were greeted upon arrival by Rafaello, our host, who was very helpful in getting us situated for our 5 night stay. The house is lovely, surrounded by the olive trees. The pool is pristine because Raffi comes to clean it every day. We did laundry in the unique washer and hung out the clothes on the drying rack that was provided. The views of the Tuscan countryside are lovely. Central location makes it easy to visit other Tuscan towns like Cortona, Siena, Montepulciano. I would recommend this...
Private Pool & Cottage for 6 in Secluded Hamlet Spectacular Views 7 km to Corton
Pool
Belvilla by OYO Sparsa Girasole
10.0 out of 10, Exceptional, (1)
Belvilla by OYO Sparsa Girasole
Pool
Belvilla by OYO Loggia
10.0 out of 10, Exceptional, (7)
Belvilla by OYO Loggia
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Pool
beautiful tuscan villa with pool, ideal for groups
10.0 out of 10, Exceptional, (21)
"If you are looking for a perfect Villa in Tuscany, this is it. Set in a magical hillside location, the view from the pool is a magnificent panorama of the Tuscan countryside. The house itself easily has four large double bedrooms and one twin. It's ideal for groups - there's space for large social gatherings as well as different areas to provide privacy for separate groups. We can't wait to go back one day!"
beautiful tuscan villa with pool, ideal for groups
Property grounds
La Pergola typical Tuscan house with wonderful panorama
10.0 out of 10, Exceptional, (7)
"This Villa was amazing, Irene was always in touch through the whole process. The villa is every bit as stunning as in the pictures. You pass Cortona and drive up a old Roman gravel road. (You will need a car for this property, I recommend a suv type vehicle). When you reach to top of the hill sits the villa, overlooking the whole valley. We were greeted with wine and olive oil. The villa consists of an upstairs where bedrooms, bathroom, and sitting room are located. Downstairs is the kitchen,...
La Pergola typical Tuscan house with wonderful panorama
Pool
Cosy cottage with large private pool and perfectly mantained garden - 2-BR
10.0 out of 10, Exceptional, (1)
"The management company welcomed us to the property. The amenities were excellent with a private swimming pool. Written instructions for the washing machine, dishwasher and garbage disposal would have been helpful"
Cosy cottage with large private pool and perfectly mantained garden - 2-BR
Fridge, microwave, oven, dishwasher
Belvilla by OYO Cicerchia
10.0 out of 10, Exceptional, (8)
"Beautiful apartment with all the amenities you would hope for. Amazing gift basket of brioche, pastries, bread, crackers, jams, honey, coffee and milk. Surrounded by gorgeous pasture and olive groves. Close to Cortona and local grocery store and restaurants. Easy to drive to Arrizo, Perugia and all the beautiful villages around Umbria. Our host Carola was so wonderful and so very helpful. She went above and beyond to make sure we were well taken care of. I wish we could have stayed longer."
Belvilla by OYO Cicerchia
Property grounds
Elegante Appartamento nel Centro Storico di Cortona
10.0 out of 10, Exceptional, (2)
"Beautiful apartment right in the centre of cortona. Lots of churches, museum and restaurants close by with interesting architecture and good food. Shops selling local linen, leather items and Italian cashmere. Wonderful place to experience Italian culture and cuisine"
The price is CA $142
CA $168 total
includes taxes & fees
May 29 - May 30
Elegante Appartamento nel Centro Storico di Cortona
Outdoor dining
Maya Luxury Home - private garden for breathtaking view, nearby the centre
10.0 out of 10, Exceptional, (2)
"I've stayed at many different properties in Cortona. This one is more modern than I prefer but it was fantastic! My back appreciated the wonderful bed and my love of cooking appreciated the larger sized refrigerator, freezer and cooking appliances. But most of all...the view...how can I describe? At the risk of not being able to get this property because it's so good, I have to tell you the view is stunning! I love Casa Maya!"
Maya Luxury Home - private garden for breathtaking view, nearby the centre
Interior
The Old Fashion House
10.0 out of 10, Exceptional, (1)
"I recently had the pleasure of staying in this vacation rental, and I cannot say enough good things about it. From start to finish, my experience was absolutely fantastic. First and foremost, the apartment itself is a gem. It's beautifully decorated, spacious, and immaculately clean. As soon as I walked in, I was struck by the tasteful design and attention to detail. The living area is cozy and inviting, perfect for relaxing after a day of exploring. The kitchen is well-equipped with all the...
The Old Fashion House
Exterior
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
9.8 out of 10, Exceptional, (52)
"The property was built in 1500 but updated recently. It definitely has its quirks related to gas and electricity. More written instructions in the home would be useful. The home is spacious with the exception of the galley style kitchen. There is a lovely courtyard that seems to be very unique to properties within the walls of Cortona. There are a couple of nice walks around Cortona. You are not too far from Sienna for a day trip."
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Exterior
Bramasole by Interhome
9.8 out of 10, Exceptional, (9)
"great"
Bramasole by Interhome
Pool
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga
9.6 out of 10, Exceptional, (4)
"The villa was so comfortable and lovely. Michele was very responsive and helpful. 10/10 experience."
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga
Aerial view
Martina by Interhome
9.4 out of 10, Exceptional, (13)
"Lovely farm, quiet and peaceful. A good location as a home base to explore Tuscany and Umbria by car. A few amenities in the house would have been helpful such as cleaning supplies, soap, salt, sugar, pepper, laundry detergent, so that we didn't have to buy essentials which we had to leave behind."
Martina by Interhome
Exterior
Podere Casorbica with free parking, large garden, swimming pool.
9.2 out of 10, Wonderful, (9)
"We are a family of five and found the property ideal for our needs, the children occupied the first floor whilst mum and dad occupied the ground floor, both have a kitchen area and lovely bathrooms with ample space to dine together on the ground floor. The property was clean and is very well maintained. The owner Giorgio met us on our arrival and managed to answer any questions we had with the help of google translate and actually came to the property every morning to clean the pool, this was...
Podere Casorbica with free parking, large garden, swimming pool.
Exterior
Nice house in the country of Cortona.
9.2 out of 10, Wonderful, (9)
"The house was neatly kept and quiet. Cortana was visible on the hill. Marzi was friendly and helpful in meeting our needs The down side was a pot holed rural road to get here and cool living room temperatures the first few days as it took the masonry walls time to warm up in the cool March temperatures."
Nice house in the country of Cortona.
Outdoor pool
Casa Fontelunga Tuscan holiday villa with private pool
9.2 out of 10, Wonderful, (7)
"2 couples used this as our base to visit nearby places- Montepulciano, Assisi. Gorgeous place, wonderful landlord. Secluded, beautiful views"
Casa Fontelunga Tuscan holiday villa with private pool
Outdoor pool
"Gabolandia", a holiday home in Cortona
9.2 out of 10, Wonderful, (5)
"We were pleasantly suprised by the hospitality of our hosts - nothing was an exra mile for them in trying to help or please their guests. Many special thanks to Marzia and Massiamo and all their big and friendly family for being the wonderful hosts. The house we stayed in is spacious and clean and had everything we need. The place is a real countryside gem - quiet and full of active leasure options. We really enjoyed our holiday at this place and would recommend it to anyone wishing a restful...
"Gabolandia", a holiday home in Cortona
Pool
Small stone farmhouse overlooking Cortona with private pool and garden
9.0 out of 10, Wonderful, (2)
"Nous avons passé un très bon séjour dans cette maison. pour une maison pouvant héberger 4 personnes, la piscine est d'une taille formidable, (12*4 environ je pense). la vue de la piscine sur toute la vallée est incroyable et permet de profiter de coucher de soleil merveilleux sur Cortone. la maison est bien équipée pour la cuisine, dans les chambres il n'y a pas ou peu de rangements c'est dommage. et ce qui nous a vraiment gêné ce sont les chiens des voisins enfermés toute la journée et qui...
Small stone farmhouse overlooking Cortona with private pool and garden
Pool
La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno
7.4 out of 10, Good, (3)
"Un luogo che ha lasciato tutti noi (sia adulti che bambini) a bocca aperta: un paradiso terrestre! Per chi ama la natura, vuole staccare dalla caotica vita quotidiana e godere del tempo con i propri cari , questo è il posto che offre tutto ciò e di più! Non conoscendo bene la zona siamo arrivati un po’ impreparati ma tutto si è risolto con un viaggio al supermercato vicino Cortona! *essendo immersi nella natura c’è’ da far conto di insetti e possibili cervi e cinghiali, che rendono questo posto...
La Fattoria, a farmhouse in Cortona with a panoramic view of Lake Trasimeno
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Cortona

Pool
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, (55)
"Where to even begin? We loved everything about our stay. Stefania was wonderful, and responsive to our many questions before we even arrived. Upon arrival, it felt like a dream. The Villa is beautiful, private, and expansive. The property is huge, with lots of olive trees, fig trees, and places for the kids to play and explore. And not to mention the stunning pool, which overlooks the most incredible views of Cortona. We were pleased to find a ping pong table, and just absolutely loved the pool...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Outdoor dining
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.8 out of 10, Exceptional, (54)
"This is a wonderful property in a quiet area, but only a short walk to the piazza and restaurants. The only improvement I would recommend is the shower caddy; all of my travel sized items kept falling out of it."
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
La Finestra sul Teatro
9.8 out of 10, Exceptional, (29)
"This unit met and exceeded our expectations! The host was extremely friendly and helpful, and this well-stocked home has a perfect location within the best area of Cortona. I highly recommend this unit to anyone wishing for a clean, 'light & bright' home within walking distance to everything you would ever want to do here. Thank you, Rossana, for sharing your home with us, we look forward to our next visit!"
The price is CA $214
CA $310 total
includes taxes & fees
Jun 2 - Jun 3
La Finestra sul Teatro
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Cortona Vacation Homes information

Number of reviews
80
Accommodation
190 Vacation Homes
Lowest Price
Highest Price

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