Title: Cortona Villas from CA $130 | 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://images.trvl-media.com/place/601360/f4054673-52dd-4f97-8d57-389d1f349940.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Search Cortona Villa Rentals from CA $130

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## Check prices for these dates

Next weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=601360&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Cortona villas

![Exterior](https://images.trvl-media.com/lodging/40000000/39140000/39138300/39138214/144c6347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/40000000/39140000/39138300/39138214/f3d4501e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/40000000/39140000/39138300/39138214/5cb185bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/40000000/39140000/39138300/39138214/17368504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Cortona

[](https://www.expedia.ca/Cortona-Hotels-VILLA-CORTONESE-Fifteen-Bedroom-Villa.h39138214.Hotel-Information)

CA $8,646

CA $8,646 total

includes taxes & fees

Dec 25 - Dec 26

[](https://www.expedia.ca/Cortona-Hotels-VILLA-CORTONESE-Fifteen-Bedroom-Villa.h39138214.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/113000000/112100000/112093300/112093273/21c57ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112100000/112093300/112093273/d6356e07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/113000000/112100000/112093300/112093273/534b658d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112100000/112093300/112093273/2f8c0019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Cortona

[](https://www.expedia.ca/Cortona-Hotels-Villa-Residenza-2-With-Shared-Pool.h112093273.Hotel-Information)

CA $499

CA $566 total

includes taxes & fees

Jan 8 - Jan 9, 2026

[](https://www.expedia.ca/Cortona-Hotels-Villa-Residenza-2-With-Shared-Pool.h112093273.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33960000/33950400/33950320/8e3ae797.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace, books, music library, stereo](https://images.trvl-media.com/lodging/34000000/33960000/33950400/33950320/65121f59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33960000/33950400/33950320/3c64c478.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33960000/33950400/33950320/7bfcd509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Cortona

[](https://www.expedia.ca/Cortona-Hotels-Tuscan-Dream-Gorgeous-Private-Cortona-House-With-Fantastic-Views.h33950320.Hotel-Information)

10/10

Exceptional

(27)

"Great location with gorgeous views over the Chiana hills, and nearby restaurants. We enjoyed discovering Cortona and several hill towns in the ares"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Patricia H.

CA $462

CA $527 total

includes taxes & fees

Dec 31 - Jan 1, 2026

[](https://www.expedia.ca/Cortona-Hotels-Tuscan-Dream-Gorgeous-Private-Cortona-House-With-Fantastic-Views.h33950320.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)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112100000/112093300/112093264/8c5208e3.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)

![TV, fireplace](https://images.trvl-media.com/lodging/113000000/112100000/112093300/112093264/2bc1fcaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Cortona

[](https://www.expedia.ca/Cortona-Hotels-Villa-Loft-With-Shared-Pool.h112093264.Hotel-Information)

CA $736

CA $804 total

includes taxes & fees

Jan 8 - Jan 9, 2026

[](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)

![Standard Triple Room | Bathroom](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/c721d6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/27000000/26500000/26500000/26499959/4f173bce.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)

### Villa in Foiano della Chiana

[](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information)

8.4/10

Very good

(24)

"Good house for one night. "

![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg)

Heiner

CA $115

CA $130 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Agriturismo-Artisti-Del-Cavallo.h26499959.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/87000000/86170000/86163100/86163088/62520007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/87000000/86170000/86163100/86163088/6f9d8ac1.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/e34058f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in La Valle

[](https://www.expedia.ca/Magione-Hotels-Villa-Graziella.h86163088.Hotel-Information)

9.6/10

Exceptional

(7)

"excellent stay. Beautiful pool, well equipped kitchen, very friendly host.Perfect for the visit of the surrondigns: Perugia, the lake, Montepulciano."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

cinzia c.

CA $157

CA $270 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Magione-Hotels-Villa-Graziella.h86163088.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/39000000/38720000/38715500/38715449/5fda0375.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)

![Exterior](https://images.trvl-media.com/lodging/39000000/38720000/38715500/38715449/e8b12160.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)

### Villa in Campiglia d'Orcia

[](https://www.expedia.ca/Castiglione-DOrcia-Hotels-A-Delicious-Farmhouse-In-The-Countryside-Where-Only-The-Wind-Blows.h38715449.Hotel-Information)

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 $1,534

CA $2,509 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Castiglione-DOrcia-Hotels-A-Delicious-Farmhouse-In-The-Countryside-Where-Only-The-Wind-Blows.h38715449.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/d6476b51.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)

![Terrace/patio](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/ff9693c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/a8ccbf55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Sinalunga

[](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information)

10/10

Exceptional

(59)

"Amazing property! Could not recommend more."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Annika P.

CA $240

CA $274 total

includes taxes & fees

Dec 27 - Dec 28

[](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.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)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122120000/122116900/122116830/a8294550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/123000000/122120000/122116900/122116830/9e6a1fb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122120000/122116900/122116830/5fd644fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Toscana

[](https://www.expedia.ca/San-Casciano-Dei-Bagni-Hotels-Vrbo-Property.h122116830.Hotel-Information)

CA $4,036

CA $5,023 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/San-Casciano-Dei-Bagni-Hotels-Vrbo-Property.h122116830.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/123000000/122410000/122401000/122400965/cafcc7f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/123000000/122410000/122401000/122400965/21f1fe18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122410000/122401000/122400965/a6ceac70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Travel crib, free WiFi](https://images.trvl-media.com/lodging/123000000/122410000/122401000/122400965/26ce7e12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Subbiano

[](https://www.expedia.ca/Subbiano-Hotels-Stunning-Villa-For-2-People-With-Pool.h122400965.Hotel-Information)

CA $257

CA $307 total

includes taxes & fees

Jan 10 - Jan 11, 2026

[](https://www.expedia.ca/Subbiano-Hotels-Stunning-Villa-For-2-People-With-Pool.h122400965.Hotel-Information)

![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/35000000/34020000/34019700/34019647/3e5050b8.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)

![Fitness facility](https://images.trvl-media.com/lodging/35000000/34020000/34019700/34019647/3a6ddb8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/35000000/34020000/34019700/34019647/008ec77f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Sansepolcro

[](https://www.expedia.ca/Sansepolcro-Hotels-Villa-In-Tuscany-With-View.h34019647.Hotel-Information)

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 $1,776

CA $2,607 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Sansepolcro-Hotels-Villa-In-Tuscany-With-View.h34019647.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33600000/33593500/33593401/ccf38dca.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)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33600000/33593500/33593401/3dde7670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bar (on property)](https://images.trvl-media.com/lodging/34000000/33600000/33593500/33593401/d1daa29b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Sansepolcro

[](https://www.expedia.ca/Sansepolcro-Hotels-Villa-Santarsa.h33593401.Hotel-Information)

10/10

Exceptional

(16)

"We had a great time, despite the heat. It's a bit of a drive up the mountain to Santarsa specifically, so make sure you have enough cars!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Donnacha F.

CA $1,526

CA $2,365 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Sansepolcro-Hotels-Villa-Santarsa.h33593401.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/42000000/41980000/41976900/41976843/2982989f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/42000000/41980000/41976900/41976843/1be40e4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oven, dishwasher](https://images.trvl-media.com/lodging/42000000/41980000/41976900/41976843/4838d05a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/42000000/41980000/41976900/41976843/4b7d1945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Siena

[](https://www.expedia.ca/Buonconvento-Hotels-POGGIO-AL-SOLE-Five-Bedroom-Villa.h41976843.Hotel-Information)

8.0/10

Very good

(1)

"Villa magnifique dans un environnement superbe. Les chambres sont d'un grand confort. S'agissant d'une maison récemment rénovée, quelques réglages sont à réaliser pour atteindre la perfection : nombre de fauteuils bain de soleil insuffisant, améliorer la protection solaire sur la terrasse extérieure et le nombre de fauteuils ; petites difficultés liées à l'usage du lave linge mais très vite réglées. Globalement c'est un très agréable séjour dans une magnifique demeure, rénovée avec goût et...

![France](https://a.travel-assets.com/egds/marks/flags/fr.svg)

Pierre V.

CA $2,882

CA $3,366 total

includes taxes & fees

Jan 3 - Jan 4, 2026

[](https://www.expedia.ca/Buonconvento-Hotels-POGGIO-AL-SOLE-Five-Bedroom-Villa.h41976843.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/111000000/110150000/110141200/110141199/239f0463.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)

![Interior](https://images.trvl-media.com/lodging/111000000/110150000/110141200/110141199/1995ccbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/111000000/110150000/110141200/110141199/3c6e2f31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Trequanda

[](https://www.expedia.ca/Trequanda-Hotels-Vrbo-Property.h110141199.Hotel-Information)

CA $888

CA $1,474 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Trequanda-Hotels-Vrbo-Property.h110141199.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/0ac9183c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/bed5a9c6.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)

![Dining](https://images.trvl-media.com/lodging/90000000/89590000/89589300/89589245/44cc70c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Rapolano Terme

[](https://www.expedia.ca/Rapolano-Terme-Hotels-Villa-Il-Fornacino-With-Pool.h89589245.Hotel-Information)

9.0/10

Wonderful

(4)

"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."

![Netherlands](https://a.travel-assets.com/egds/marks/flags/nl.svg)

Toon M.

CA $1,008

CA $1,408 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Rapolano-Terme-Hotels-Villa-Il-Fornacino-With-Pool.h89589245.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/95000000/94880000/94877600/94877519/4301d1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/95000000/94880000/94877600/94877519/87be7d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/95000000/94880000/94877600/94877519/8c9b224e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/95000000/94880000/94877600/94877519/4f1f9f71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Piegaro

[](https://www.expedia.ca/Piegaro-Hotels-Entire-Villa-For-Exclusive-Use-With-Infinity-Pool-And-Professional-Kitchen.h94877519.Hotel-Information)

CA $1,755

CA $2,141 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Piegaro-Hotels-Entire-Villa-For-Exclusive-Use-With-Infinity-Pool-And-Professional-Kitchen.h94877519.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/96000000/95200000/95197700/95197667/0421c5f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95200000/95197700/95197667/7062471e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/96000000/95200000/95197700/95197667/a871a368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/96000000/95200000/95197700/95197667/55e759fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Arezzo

[](https://www.expedia.ca/Arezzo-Hotels-Villa-Bottaia-Homelike-Villas.h95197667.Hotel-Information)

[](https://www.expedia.ca/Arezzo-Hotels-Villa-Bottaia-Homelike-Villas.h95197667.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/37000000/36110000/36109900/36109853/e3845e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/37000000/36110000/36109900/36109853/bfb796da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/37000000/36110000/36109900/36109853/26b1f97d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/37000000/36110000/36109900/36109853/311f00a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Cortona

[](https://www.expedia.ca/Castiglion-Fiorentino-Hotels-VILLA-LEOPOLDINA-Nine-Bedroom-Villa.h36109853.Hotel-Information)

10/10

Exceptional

(1)

"The villa was simply awesome and perfect for our family holiday."

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Caroline H.

CA $1,153

CA $1,153 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Castiglion-Fiorentino-Hotels-VILLA-LEOPOLDINA-Nine-Bedroom-Villa.h36109853.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112370000/112368800/112368731/e89790c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112370000/112368800/112368731/0584a19e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112370000/112368800/112368731/4fcbe3dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112370000/112368800/112368731/f9d2ab10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Montepulciano

[](https://www.expedia.ca/Sarteano-Hotels-VILLA-CORTE-ANTICA-Seven-Bedroom-Villa.h112368731.Hotel-Information)

CA $3,746

CA $3,746 total

includes taxes & fees

Jan 9 - Jan 10, 2026

[](https://www.expedia.ca/Sarteano-Hotels-VILLA-CORTE-ANTICA-Seven-Bedroom-Villa.h112368731.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)

![4 bedrooms, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106910000/106903800/106903701/8f519c17.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)

### Villa in Foiano della Chiana

[](https://www.expedia.ca/Foiano-Della-Chiana-Hotels-Wonderful-Villa-With-Private-Pool-Near-Arezzo.h106903701.Hotel-Information)

CA $1,841

CA $2,559 total

includes taxes & fees

Dec 26 - Dec 27

[](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.

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## Top Cortona Hotel Reviews

![Monastero di Cortona Hotel & Spa](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/cea3a0e9_y.jpg)

### Monastero di Cortona Hotel & Spa

10/10 Excellent

"Everything was perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!"

[](https://expedia.ca/Cortona-Hotels-Monastero-Di-Cortona-Hotel-Spa.h23264410.Hotel-Information)

![Hotel Italia](https://images.trvl-media.com/lodging/2000000/1670000/1664000/1663916/22c9fd1e_y.jpg)

### Hotel Italia

10/10 Excellent

"The hotel amenities, comfort, hospitality are top notch. Should easily be a 4-star hotel! "

[](https://expedia.ca/Cortona-Hotels-Hotel-Italia.h1663916.Hotel-Information)

![Villa Santa Margherita](https://images.trvl-media.com/lodging/84000000/83490000/83480500/83480427/0897360d_y.jpg)

### Villa Santa Margherita

10/10 Excellent

"The room was large and very clean. Breakfast was very good. Will stay there if I return to Cortona"

[](https://expedia.ca/Cortona-Hotels-Villa-Santa-Margherita.h83480427.Hotel-Information)

![Il Falconiere - Relais e Chateaux](https://images.trvl-media.com/lodging/1000000/530000/528500/528472/2334a48c_y.jpg)

### Il Falconiere - Relais e Chateaux

10/10 Excellent

"Excellent staff and experiences! We had a wonderful time."

[](https://expedia.ca/Cortona-Hotels-Relais-Il-Falconiere.h528472.Hotel-Information)

![Hotel Villa Marsili](https://images.trvl-media.com/lodging/1000000/930000/922700/922648/c5455b25_y.jpg)

### Hotel Villa Marsili

10/10 Excellent

"Most comfortable room and bed beds that we stayed in the whole time we were in Italy! Also, the breakfast was 10 out of 10! Much better than the five star hotel that we stayed at in Rome and Florence. "

[](https://expedia.ca/Cortona-Hotels-Hotel-Villa-Marsili.h922648.Hotel-Information)

![Villa di Piazzano - Small Luxury Hotel of the World](https://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)

![B&B Piccolo Hotel](https://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)

![Locanda agli Amici](https://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](https://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)

## Find out more about Cortona

## Cortona Villas information

| Number of reviews | 114        |
| ----------------- | ---------- |
| Accommodation     | 499 Villas |
| Lowest Price      | CA $130    |
| Highest Price     | CA $8,646  |

## Frequently asked questions

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