Title: Cortona Villas from CA $120 | Expedia.ca [Cortona Travel Guide](https://expedia.ca/Cortona.dx601360)[Hotels in Cortona](https://expedia.ca/Cortona-Hotels.d601360.Travel-Guide-Hotels)[Vacation Rentals in Cortona](https://expedia.ca/Cortona-Vacation-Rentals.d601360.Travel-Guide-VacationRentals)[Flights to Cortona](https://expedia.ca/Cheap-Flights-To-Cortona.d601360.Travel-Guide-Flights)[Things to do in Cortona](https://expedia.ca/Things-To-Do-In-Cortona.d601360.Travel-Guide-Activities)[Cortona Car Rentals](https://expedia.ca/Car-Rentals-In-Cortona.d601360.Car-Rental-Guide)[Cortona Vacation Packages](https://expedia.ca/Cortona.d601360.Destination-Travel-Guides) ![Cortona showing a city and farmland](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/157000/157531-Arezzo-Province.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Cortona Villa Rentals from CA $120 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Cortona Villas ![Exterior](https://images.trvl-media.com/lodging/113000000/112100000/112093300/112093273/21c57ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112100000/112093300/112093273/52dc2b50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112100000/112093300/112093273/8a63955c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112100000/112093300/112093273/2b578eb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning Cortona CA $503 CA $571 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Cortona-Hotels-Villa-Residenza-2-With-Shared-Pool.h112093273.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89730000/89722400/89722378/a406b090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![9 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89730000/89722400/89722378/e9868e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/90000000/89730000/89722400/89722378/de8afb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/90000000/89730000/89722400/89722378/9e2662cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo Cortona CA $812 CA $820 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Cortona-Hotels-Agriturismo-Pierle-Cuiano-Villa-With-Mountain-View.h89722378.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112100000/112093300/112093264/4e4955e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/113000000/112100000/112093300/112093264/96093821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112100000/112093300/112093264/ad9f4727.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/113000000/112100000/112093300/112093264/36ac7799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 'Loft' with Shared Pool, Wi-Fi and Air Conditioning Cortona CA $742 CA $810 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Cortona-Hotels-Villa-Loft-With-Shared-Pool.h112093264.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/8208f9d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/e04fd69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/e80eba77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/100f6cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Artisti del Cavallo Tourism Foiano della Chiana 8.4/10 Very good (24) "Ottimo agriturismo silenzioso con persone molto gentilissime " ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) GIANCARLO CA $106 CA $120 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/87000000/86170000/86163100/86163088/4ea4295f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/87000000/86170000/86163100/86163088/304acfc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/87000000/86170000/86163100/86163088/e7d80660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/87000000/86170000/86163100/86163088/118d8355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Graziella, Romantic Perugia La Valle 9.6/10 Exceptional (7) "Perfekte Lage um Umbrien zu erkunden und einen Abstecher in die Toskana zu machen. Die Unterkunft war wie beschrieben. Die Kommunikation mit dem Vermieter lief gut. Kleiner Makel, bei einem Aufenthalt von 14 Tagen sollte zur Hälfte der Zeit die Bettwäsche und die Handtücher gewechselt werden. In der 2.Woche waren die Nächte relativ kühl (15), da hat die Überdecke zum Laken gefehlt. Sonst alles prima." ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Joerg R. CA $158 CA $273 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Magione-Hotels-Villa-Graziella.h86163088.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/6a82a5cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/8099b959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/cc976759.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/f6eed317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Il Poggio dell'Eremita Sinalunga 10/10 Exceptional (57) "Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vivian K. CA $192 CA $224 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38720000/38715500/38715449/f30bb46d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/39000000/38720000/38715500/38715449/efafc033.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/39000000/38720000/38715500/38715449/39cefede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38720000/38715500/38715449/67e96970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### '...a delicious farmhouse in the countryside where only the wind blows...' Campiglia d'Orcia 10/10 Exceptional (7) "We had a wonderful stay at the villa - we were a group of 10 adults and 2 children and used the villa as our home base for a week to explore the area (Pienza, Siena, Montalcino, Montelpulciano, etc). There are 4 apartments ranging from 1-3 bedrooms which were fantastic for the families, plus an additional communal kitchen and living room for everyone to gather. It was the perfect setup as it gave everyone the ability to have some privacy as well as for everyone to congregate and eat meals... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Li-Shen L. CA $1,543 CA $2,523 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Castiglione-DOrcia-Hotels-A-Delicious-Farmhouse-In-The-Countryside-Where-Only-The-Wind-Blows.h38715449.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/123000000/122120000/122116900/122116830/651722a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/123000000/122120000/122116900/122116830/b5551068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122120000/122116900/122116830/b8844922.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122120000/122116900/122116830/e4816817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Godiluva, wine villa Toscana CA $4,061 CA $5,032 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/San-Casciano-Dei-Bagni-Hotels-Vrbo-Property.h122116830.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/93000000/92020000/92017400/92017313/cb2e18d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92020000/92017400/92017313/a0cc75da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92020000/92017400/92017313/42b859d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92020000/92017400/92017313/b0affea6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa "Il Rancho Grande" with Private Pool, Private Terrace & Wi-Fi Città di Castello 10/10 Exceptional (1) "Pros: Mi è piaciuto tutto" ![Italy](https://a.travel-assets.com/egds/marks/flags/it.svg) Anonymous traveller CA $1,569 CA $1,770 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Citta-Di-Castello-Hotels-Villa-Il-Rancho-Grande-With-Private-Pool.h92017313.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/99000000/98680000/98678000/98677913/aad9a61e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/99000000/98680000/98678000/98677913/b1fb6b00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/99000000/98680000/98678000/98677913/12a15a02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/99000000/98680000/98678000/98677913/93826d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w Trequanda CA $351 CA $428 total includes taxes & fees Nov 15 - Nov 16 [](https://www.expedia.ca/Trequanda-Hotels-Vrbo-Property.h98677913.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/97000000/96930000/96929600/96929584/b8becf6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/97000000/96930000/96929600/96929584/dc1accab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96930000/96929600/96929584/67e881db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96930000/96929600/96929584/391c8e56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa il Moro, splendid landscapes in the heart of Tuscany Montalcino 10/10 Exceptional (2) "What an absolute gem in the Tuscan hills. Beautiful home, all the comforts we needed, well stocked kitchen, lots of bathrooms, lovely pool and spectacular views. Caretake Luca is on site which is very helpful. Stella made check-in a breeze. Would not hesitate to come back " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Sharon E. [](https://www.expedia.ca/Montalcino-Hotels-Villa-Il-Moro.h96929584.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110150000/110141200/110141199/3c6e2f31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110150000/110141200/110141199/e9dc4843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110150000/110141200/110141199/239f0463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110150000/110141200/110141199/67aa0495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Heart - relax with those you love in Tuscany. Trequanda CA $893 CA $1,490 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Trequanda-Hotels-Vrbo-Property.h110141199.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/47000000/46080000/46073000/46072990/7e0e6f3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/47000000/46080000/46073000/46072990/187c2360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, internet](https://images.trvl-media.com/lodging/47000000/46080000/46073000/46072990/0bd47223.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/47000000/46080000/46073000/46072990/f3fb0ed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### VILLA FELICE - Three Bedroom Villa, Sleeps 6 Perugia CA $3,866 CA $3,866 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Perugia-Hotels-VILLA-FELICE-Three-Bedroom-Villa.h46072990.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/103000000/102320000/102314800/102314787/4b0b6e16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102320000/102314800/102314787/40b449e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102320000/102314800/102314787/0379f724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102320000/102314800/102314787/d30adf33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Podere Manafiore - historical villa with swimming pool Monticchiello 10/10 Exceptional (1) "the villa was all we hoped for. Directions finding the villa was not clear, it took us for ever to locate the villa. The road to the villa was hardly drivable. It was wonderfully furnished. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caroline R. [](https://www.expedia.ca/Pienza-Hotels-Podere-Manafiore-Historical-Villa-With-Swimming-Pool.h102314787.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/1654ecb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/24ff1535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/0ac9183c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/f9f06ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa "Il Fornacino" with Pool, Garden & Wi-Fi Rapolano Terme 9.0/10 Wonderful (4) "Pros: Die Villa war mit viel Liebe zum Detail eingerichtet. Jedes Schlafzimmer verfügt über ein eigenes Bad. Besonders hervorzuheben ist der tolle Pool, der uns während der Hitzewellw in der letzten Woche genügend Abkühlung verschafft hat. Benedetta ist eine sehr nette Gastgeberin, die alle 2 Tage zum Pool säubern vorbei kam. Alles in allem ein toller Urlaub, in dem auch viel in der bezaubernden Küche gekocht wurde. Cons: Die vielen Mücken" ![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg) Anonymous traveller CA $792 CA $1,195 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Rapolano-Terme-Hotels-Villa-Il-Fornacino-With-Pool.h89589245.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/40000000/39950000/39940300/39940283/88595684.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/40000000/39950000/39940300/39940283/180-c242e5f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39950000/39940300/39940283/4a11a5f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/40000000/39950000/39940300/39940283/180-a5801bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo Arezzo 10/10 Exceptional (18) "The property had beautiful gardens, well appointed apartments and a gracious and always helpful host. Children enjoyed the pool a great deal during hot afternoons. Conveniently located for day trips by train or car to Florence and historic and scenic hill towns." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John N. CA $2,745 CA $3,794 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Arezzo-Hotels-Spacious-Villa-Noble-With-All-The-Comfort.h39940283.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/123000000/122090000/122085700/122085615/9fb80fd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/123000000/122090000/122085700/122085615/c66f1b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122090000/122085700/122085615/77ba9d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122090000/122085700/122085615/7401c4ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa 'Tiberini - Casale Il Pecino' with Lake View, Private Pool and Wi-Fi Torrita di Siena [](https://www.expedia.ca/Torrita-Di-Siena-Hotels-Villa-Tiberini-Casale-Il-Pecino-With-Lake-View.h122085615.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34020000/34019700/34019647/296f6cf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34020000/34019700/34019647/cbcc1729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34020000/34019700/34019647/d235ccce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/35000000/34020000/34019700/34019647/3a6ddb8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Cantone with view, private pool and private SPA, perfect for groups! Sansepolcro 10/10 Exceptional (15) "Villa Cantone was perfect for our family group of 22 people. It meet all our needs and provided us with the holiday of a lifetime. The hosts were very attentive and nothing seemed too much for them." ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Geoffrey P. CA $1,787 CA $2,627 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Sansepolcro-Hotels-Villa-In-Tuscany-With-View.h34019647.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33600000/33593500/33593401/4d7bb041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33600000/33593500/33593401/5a1a5ae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/34000000/33600000/33593500/33593401/d2b1f996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33600000/33593500/33593401/196c638f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Santarsa, 31 people, magnificent views and private pool, no neighbors Sansepolcro 10/10 Exceptional (16) "Chiara hosted our wedding weekend. I can not stress enough that pictures on here don't do the property justice. It is one of the most spectacular villas we have ever seen. Chiara (the host) is so lovely and very attentive. The place it swlf has got so much space, so much offer and is so wonderful, we're hoping to go back for our 10 year anniversary." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Monika L. CA $1,535 CA $2,378 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Sansepolcro-Hotels-Villa-Santarsa.h33593401.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106910000/106903800/106903701/7fe649ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106910000/106903800/106903701/3d53eb9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/107000000/106910000/106903800/106903701/1fea1aac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106910000/106903800/106903701/64ad74f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wonderful villa with private pool near Arezzo Foiano della Chiana CA $1,852 CA $2,575 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Wonderful-Villa-With-Private-Pool-Near-Arezzo.h106903701.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24®ionId=601360&adults=2&lodging=VILLA&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FCortona-Villas.d601360-aaVillas.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCortona-Villas.d601360-aaVillas.Travel-Guide-Accommodation) ## Top Cortona Hotel Reviews ![Villa di Piazzano - Small Luxury Hotel of the World](//images.trvl-media.com/lodging/1000000/980000/972000/971985/473f66a9_y.jpg) ### Villa di Piazzano - Small Luxury Hotel of the World 10/10 Excellent "Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly " [](https://expedia.ca/Cortona-Hotels-Villa-Di-Piazzano-Small-Luxury-Hotel-Of-The-World.h971985.Hotel-Information) ![Monastero di Cortona Hotel & Spa](//images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/cea3a0e9_y.jpg) ### Monastero di Cortona Hotel & Spa 10/10 Excellent "What a unique place. Near the top of the hill. Staff service and amenities were all great. Not an easy place to drive to. The taxis drive-in backwards the last eighth of a mile." [](https://expedia.ca/Cortona-Hotels-Monastero-Di-Cortona-Hotel-Spa.h23264410.Hotel-Information) ![Hotel Villa Marsili](//images.trvl-media.com/lodging/1000000/930000/922700/922648/c5455b25_y.jpg) ### Hotel Villa Marsili 10/10 Excellent "Everything about this hotel was fabulous! Very helpful and friendly staff, beautiful spacious room with an amazing view, and the food!!! Breakfast, happy hour and night time cookie snacks - all just the best. Can’t recommend this hotel enough. Would definitely stay here again!" [](https://expedia.ca/Cortona-Hotels-Hotel-Villa-Marsili.h922648.Hotel-Information) ![Il Falconiere - Relais e Chateaux](//images.trvl-media.com/lodging/1000000/530000/528500/528472/2334a48c_y.jpg) ### Il Falconiere - Relais e Chateaux 10/10 Excellent "What an incredible stay at Il Falconiere! Exceptional service and unforgettable experiences — from Silvia Baracchi’s amazing cooking class to an unbelievable dinner at the Michelin-starred restaurant. Breakfast in the glass room overlooking the Tuscan hills was pure magic. We loved wandering through Cortona — charming streets, fantastic restaurants, and surprisingly great shopping. Already dreaming of our next visit! " [](https://expedia.ca/Cortona-Hotels-Relais-Il-Falconiere.h528472.Hotel-Information) ![B&B Piccolo Hotel](//images.trvl-media.com/lodging/13000000/12240000/12234700/12234603/ab339a34_y.jpg) ### B&B Piccolo Hotel 10/10 Excellent "We were able to drive up to the door and leave our car with staff. Staff was amazing. Breakfast had many options and always replenished. It is right off the main piazza. Would stay again for sure!" [](https://expedia.ca/Cortona-Hotels-BB-Piccolo-Hotel.h12234603.Hotel-Information) ![Hotel San Luca](//images.trvl-media.com/lodging/3000000/2700000/2691400/2691302/5cf5bba0_y.jpg) ### Hotel San Luca 10/10 Excellent "great view, very clean, friendly staff" [](https://expedia.ca/Cortona-Hotels-Hotel-San-Luca.h2691302.Hotel-Information) ![Locanda agli Amici](//images.trvl-media.com/lodging/91000000/90310000/90300600/90300548/5a958be8_y.jpg) ### Locanda agli Amici 10/10 Excellent "Very clean and beautiful room. Amazing views! Breakfast and staff were the best!" [](https://expedia.ca/Cortona-Hotels-Locanda-Agli-Amici.h90300548.Hotel-Information) ![Villa Borgo San Pietro](//images.trvl-media.com/lodging/2000000/1680000/1677700/1677691/12bc3783_y.jpg) ### Villa Borgo San Pietro 10/10 Excellent "Excellent staff. They went above and beyond. Someone in our party was ill and they suggested they would call a doctor and he would come to the resort. Within an hour the Dr arrived assessed situation provided prescription so our vacation was not disrupted. Excellent. " [](https://expedia.ca/Cortona-Hotels-Villa-Borgo-San-Pietro.h1677691.Hotel-Information) ![Luxury Cortona view hilltop Villa](//images.trvl-media.com/lodging/29000000/28850000/28840500/28840420/73d0cc6c_y.jpg) ### Luxury Cortona view hilltop Villa 10/10 Excellent "Beautiful villa of your dreams on a hillside near Cortona. Everything was exactly as described and the villa is very large. We had 4 couples each in the 4 master bedrooms which are huge and very nicely separated. Be aware the road up to the villa is very challenging! This is not walking distance or walkable to anything but within 10-15 minutes to Cortona. Not a problem for us at all. Very quiet, very beautiful, fantastic location to explore Tuscany and Umbria. Very large kitchen! We had the team there prepare us all a dinner one night and it was one of our favorite meals of the entire trip." [](https://expedia.ca/Cortona-Hotels-Luxury-Cortona-View-Hilltop-Villa.h28840420.Hotel-Information) ## Find out more about Cortona ## Cortona Villas information | Number of reviews | 110 | | --- | --- | | Accommodation | 508 Villas | | Lowest Price | CA $120 | | Highest Price | CA $3,866 | ## Frequently asked questions ### How much do villas in Cortona cost? > Rates for villas in Cortona range between CA $120 and CA $3,866 per night. Whatever your budget, you can find someplace that fits your needs with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### How many villas are there in Cortona? > Cortona has 508 villas to choose from. Find a stay that's right for you quickly and easily by checking the "Villa" box under the "Property type" tab in our handy filter tool. ### Why book your villa in Cortona with Expedia? > Use Expedia to find your ideal villa in Cortona. Taking the kids on vacation? Make the most of our helpful filters to search for stays with amenities like WiFi and a pool. If you need to stick to a budget, choose how much you're willing to spend and the star rating of the property. We'll help you find a perfect place that suits your taste and style. ### How can I find cheap villas in Cortona? > With Expedia's filter tool, scoring cheap villas in Cortona is easy. To discover options that'll make your wallet smile, fine-tune your search by amenities, star rating and budget. ### What is there to do near my villa in Cortona? > You'll find loads of impressive things to see and do in Cortona. Don't miss renowned attractions like [Palazzo Comunale](https://www.expedia.ca/Palazzo-Comunale-Cortona-Old-Town.d6102852.Vacation-Attraction), [Cathedral of Cortona](https://www.expedia.ca/Cathedral-Of-Cortona-Cortona-Old-Town.d6102846.Vacation-Attraction) and [Santa Maria Nuova](https://www.expedia.ca/Santa-Maria-Nuova-Cortona.d6102858.Vacation-Attraction). 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[Car rental Terontola](https://www.expedia.ca/Car-Rentals-In-Terontola.d6025579.Car-Rental-Guide) - [Car rental Torrita di Siena](https://www.expedia.ca/Car-Rentals-In-Torrita-Di-Siena.d6046345.Car-Rental-Guide) - [Things to do in Brolio](https://www.expedia.ca/Things-To-Do-In-Brolio.d6361222.Travel-Guide-Activities) - [Things to do in Lucignano](https://www.expedia.ca/Things-To-Do-In-Lucignano.d6048408.Travel-Guide-Activities) - [Things to do in Terontola](https://www.expedia.ca/Things-To-Do-In-Terontola.d6025579.Travel-Guide-Activities) - [Book Villas in Cortona on Expedia.it](https://www.expedia.it/Cortona-Ville.d601360-aaVille.Guida-Viaggi-Alloggi)