Skip to main content

Holiday Rentals in Cortona

Find the holiday rentals that appeal to you the most

Holiday Rentals for every style

Find the right holiday rental for you in Cortona

Top picks for Cortona hotels

Explore our most popular hotels in Cortona

Filter by:

Review score

Casa Dreosti

Cortona Old Town, Cortona

Set within 32 km of Piazza Grande and 38 km of Terme di Montepulciano, Casa Dreosti offers rooms with air conditioning and a private bathroom in Cortona.

J
Joseph
From
Italy
Excellent location, fantastic breakfast and a host who goes above and beyond.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 188 reviews
Price from
US$145.94
1 night, 2 adults

La Renaia

Cortona

Featuring a seasonal outdoor swimming pool and views of mountain, La Renaia is a farm stay situated in a historic building in Cortona, 33 km from Piazza Grande.

Z
Zsofia
From
Hungary
Lovely agriturismo near Cortona, tucked away in a secluded area. The location is excellent — perfect for exploring the surrounding region by car. Carola is very kind and a fantastic host, making sure you enjoy every moment of your stay. Our room was super comfortable and spotless, equipped with everything we needed: a huge, cozy bed; a kitchenette and fridge stocked with breakfast essentials; a coffee machine with capsules, and more. The bathroom was spacious and well-supplied with toiletries. There was even a patio. Parking was conveniently located right in front of the room, with shade. We’d gladly return anytime!
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 261 reviews
Price from
US$97.17
1 night, 2 adults

Casa del Loggiato

Cortona Old Town, Cortona

Set in Cortona, 32 km from Piazza Grande and 37 km from Terme di Montepulciano, Casa del Loggiato offers accommodation with free WiFi in a historic building.

N
Nelda
From
South Africa
Beautiful apartment giving us a real 'Tuscan' feel. Wish we could stay longer to enjoy the apartment. Location is perfect!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 156 reviews
Price from
US$106.01
1 night, 2 adults

Le Residenze Ristori

Cortona Old Town, Cortona

Set in a 17th-century building, Le Residenze Ristori offers self-catering apartments and rooms with free WiFi in the historic centre of Cortona.

S
Sloba
From
Serbia
The apartment exudes the soul of Cortona
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 852 reviews
Price from
US$84.81
1 night, 2 adults

Agriturismo Il Borgo

Cortona

Agriturismo Il Borgo is located in Cortona and features a pool with a view and garden views. This property offers access to a terrace and free private parking.

a
ann-marie
From
United Kingdom
the property was in a quiet location, it was small and unique and perfect for 2 people.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 103 reviews
Price from
US$127.21
1 night, 2 adults

Casale l'Antico Carro

Cortona

Set in Cortona, 33 km from Piazza Grande, Casale l'Antico Carro has pool with a view, parking on-site and rooms with free WiFi access.

D
Dunn
From
United Kingdom
Quite peaceful location. Family run Renovated 17th century to high standard. Great Pool and lovely large garden areas. Good continental choice breakfast. Restaurant on site and Ma Ma was doing the cooking - all freshly prepared eat inside or out. Lovely staff who made yo feel welcome.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 107 reviews
Price from
US$141.34
1 night, 2 adults

Monastero San Silvestro

Cortona

Set within 32 km of Piazza Grande and 49 km of Perugia Cathedral, Monastero San Silvestro provides rooms with air conditioning and a private bathroom in Cortona.

H
Hanna
From
Poland
Everything was perfect. Comfortable and beautiful apartaments, big garden and great pool. You can really feel Tuscany.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 336 reviews
Price from
US$145.94
1 night, 2 adults

B&B Il Mandorlo

Cortona

Offering a garden and garden view, B&B Il Mandorlo is situated in Cortona, 28 km from Piazza Grande and 38 km from Terme di Montepulciano.

R
Robert
From
Australia
Cannot recommend this B&B enough. Our stay was amazing, if you want a true Tuscan experience, this is it. The hosts were just beautiful, the property was stunning, room was huge, comfortable beds and spacious bathroom. It was immaculately clean. Views over Cortona and the valley. 10 minutes to Cortona, local wineries and sights. Loved this place!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 44 reviews
Price from
US$84.81
1 night, 2 adults

MAGNOLIA

Cortona

Featuring garden views, MAGNOLIA provides accommodation with a garden and a patio, around 38 km from Terme di Montepulciano.

M
Magdalena
From
Poland
We were traveling with friends (two couples). Everything was top notch. The beds are super comfortable, there is a well-equipped kitchen (induction hob, oven, dishwasher, microwave), a bathroom with a shower and bidet (great :)) and an additional restroom. We could freely use the garden and patio, where we ate breakfast and spent evenings surrounded by astonishing greenery. The owners are very friendly people who were more than happy to answer all our questions. Magnolia is located within perfect distance, ca. 30 min walk from Cortona (once again thanks to the hosts for pointing us a shortcuts). It's perfect solution for both people who want to spend time in the city, but also want to relax in secluded spot. We highly recommend and thank you for lovely time.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 59 reviews
Price from
US$163.72
1 night, 2 adults

La Casa di Laura

Cortona Old Town, Cortona

Offering lake views, La Casa di Laura is an accommodation set in Cortona, 37 km from Terme di Montepulciano and 47 km from Perugia Train Station.

F
Franciszek
From
Poland
There is a beautiful view from the apartment. Bruno and his daughter were super friendly and brought us from the train station to the city. The apartment is well equipped.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 35 reviews
Price from
US$129.56
1 night, 2 adults
All holiday rentals in Cortona

The best holiday rentals in Cortona

Check out our pick of great holiday rentals in Cortona

Filter by:

Review score

Casa Dreosti

Cortona Old Town, Cortona

Set within 32 km of Piazza Grande and 38 km of Terme di Montepulciano, Casa Dreosti offers rooms with air conditioning and a private bathroom in Cortona.

J
Joseph
From
Italy
Excellent location, fantastic breakfast and a host who goes above and beyond.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 188 reviews
Price from
US$145.94
1 night, 2 adults

La Renaia

Cortona

Featuring a seasonal outdoor swimming pool and views of mountain, La Renaia is a farm stay situated in a historic building in Cortona, 33 km from Piazza Grande.

Z
Zsofia
From
Hungary
Lovely agriturismo near Cortona, tucked away in a secluded area. The location is excellent — perfect for exploring the surrounding region by car. Carola is very kind and a fantastic host, making sure you enjoy every moment of your stay. Our room was super comfortable and spotless, equipped with everything we needed: a huge, cozy bed; a kitchenette and fridge stocked with breakfast essentials; a coffee machine with capsules, and more. The bathroom was spacious and well-supplied with toiletries. There was even a patio. Parking was conveniently located right in front of the room, with shade. We’d gladly return anytime!
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 261 reviews
Price from
US$97.17
1 night, 2 adults

Casa del Loggiato

Cortona Old Town, Cortona

Set in Cortona, 32 km from Piazza Grande and 37 km from Terme di Montepulciano, Casa del Loggiato offers accommodation with free WiFi in a historic building.

N
Nelda
From
South Africa
Beautiful apartment giving us a real 'Tuscan' feel. Wish we could stay longer to enjoy the apartment. Location is perfect!
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 156 reviews
Price from
US$106.01
1 night, 2 adults

Le Residenze Ristori

Cortona Old Town, Cortona

Set in a 17th-century building, Le Residenze Ristori offers self-catering apartments and rooms with free WiFi in the historic centre of Cortona.

S
Sloba
From
Serbia
The apartment exudes the soul of Cortona
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 852 reviews
Price from
US$84.81
1 night, 2 adults

Agriturismo Il Borgo

Cortona

Agriturismo Il Borgo is located in Cortona and features a pool with a view and garden views. This property offers access to a terrace and free private parking.

a
ann-marie
From
United Kingdom
the property was in a quiet location, it was small and unique and perfect for 2 people.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 103 reviews
Price from
US$127.21
1 night, 2 adults

Casale l'Antico Carro

Cortona

Set in Cortona, 33 km from Piazza Grande, Casale l'Antico Carro has pool with a view, parking on-site and rooms with free WiFi access.

D
Dunn
From
United Kingdom
Quite peaceful location. Family run Renovated 17th century to high standard. Great Pool and lovely large garden areas. Good continental choice breakfast. Restaurant on site and Ma Ma was doing the cooking - all freshly prepared eat inside or out. Lovely staff who made yo feel welcome.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 107 reviews
Price from
US$141.34
1 night, 2 adults

Monastero San Silvestro

Cortona

Set within 32 km of Piazza Grande and 49 km of Perugia Cathedral, Monastero San Silvestro provides rooms with air conditioning and a private bathroom in Cortona.

H
Hanna
From
Poland
Everything was perfect. Comfortable and beautiful apartaments, big garden and great pool. You can really feel Tuscany.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 336 reviews
Price from
US$145.94
1 night, 2 adults

B&B Il Mandorlo

Cortona

Offering a garden and garden view, B&B Il Mandorlo is situated in Cortona, 28 km from Piazza Grande and 38 km from Terme di Montepulciano.

R
Robert
From
Australia
Cannot recommend this B&B enough. Our stay was amazing, if you want a true Tuscan experience, this is it. The hosts were just beautiful, the property was stunning, room was huge, comfortable beds and spacious bathroom. It was immaculately clean. Views over Cortona and the valley. 10 minutes to Cortona, local wineries and sights. Loved this place!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 44 reviews
Price from
US$84.81
1 night, 2 adults

MAGNOLIA

Cortona

Featuring garden views, MAGNOLIA provides accommodation with a garden and a patio, around 38 km from Terme di Montepulciano.

M
Magdalena
From
Poland
We were traveling with friends (two couples). Everything was top notch. The beds are super comfortable, there is a well-equipped kitchen (induction hob, oven, dishwasher, microwave), a bathroom with a shower and bidet (great :)) and an additional restroom. We could freely use the garden and patio, where we ate breakfast and spent evenings surrounded by astonishing greenery. The owners are very friendly people who were more than happy to answer all our questions. Magnolia is located within perfect distance, ca. 30 min walk from Cortona (once again thanks to the hosts for pointing us a shortcuts). It's perfect solution for both people who want to spend time in the city, but also want to relax in secluded spot. We highly recommend and thank you for lovely time.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 59 reviews
Price from
US$163.72
1 night, 2 adults

La Casa di Laura

Cortona Old Town, Cortona

Offering lake views, La Casa di Laura is an accommodation set in Cortona, 37 km from Terme di Montepulciano and 47 km from Perugia Train Station.

F
Franciszek
From
Poland
There is a beautiful view from the apartment. Bruno and his daughter were super friendly and brought us from the train station to the city. The apartment is well equipped.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 35 reviews
Price from
US$129.56
1 night, 2 adults
All holiday rentals in Cortona

Most booked holiday rentals in Cortona and surroundings in the past month

See all

Popular with guests booking holiday rentals in Cortona

Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 336 reviews

Popular with guests booking holiday rentals in Cortona

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 103 reviews

Popular with guests booking holiday rentals in Cortona

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 156 reviews

Popular with guests booking holiday rentals in Cortona

Scored out of 10, guest rating 7.6
Good - What previous guests thought, 221 reviews

Popular with guests booking holiday rentals in Cortona

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 384 reviews

Popular with guests booking holiday rentals in Cortona

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 297 reviews

Popular with guests booking holiday rentals in Cortona

Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 261 reviews

Popular with guests booking holiday rentals in Cortona

Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 404 reviews

Popular with guests booking holiday rentals in Cortona

Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 406 reviews

Popular with guests booking holiday rentals in Cortona

Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 853 reviews

Highly rated holiday rentals in Cortona and nearby

La Casa di Iole

Cortona
8.0+ review score
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 37 reviews

Set in Cortona, 30 km from Piazza Grande and 37 km from Terme di Montepulciano, La Casa di Iole offers accommodation with free WiFi in a historic building.

From US$176.68 per night

Casa Ambra

Cortona
8.0+ review score
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 56 reviews

Located in Cortona, 30 km from Piazza Grande, Casa Ambra has free bikes, private parking and rooms with free WiFi access.

From US$170.79 per night

La Corte Di Ambra

Cortona
8.0+ review score
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 82 reviews

La Corte Di Ambra is located in Cortona's historical centre. Free Wi-Fi access is available in all areas.

From US$235.57 per night

Locanda Petrella

Cortona
8.0+ review score
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 406 reviews

With a quiet location in Cortona's pedestrian area, Locanda Petrella is a 5-minute walk from Cortona Cathedral. It is set on the second floor of a historic building dating back to the 1800s.

From US$153.12 per night

Casa Teatro

Cortona
8.0+ review score
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 28 reviews

Set in Cortona, 37 km from Terme di Montepulciano and 48 km from Perugia Train Station, Casa Teatro offers air conditioning.

From US$155.77 per night

SIGNORELLI HOUSE

Cortona
8.0+ review score
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 9 reviews

SIGNORELLI HOUSE is situated in the Cortona Old Town district of Cortona, 48 km from Perugia Train Station, 50 km from Corso Vannucci and 35 km from Magione Motorspeedway.

From US$765.60 per night
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 51 reviews

Offering city views, Casa Vacanze Beppina Cortona is an accommodation set in Cortona, 37 km from Terme di Montepulciano and 48 km from Perugia Train Station. The property has quiet street views.

From US$134.27 per night

B&B Il Rosmarino

Cortona
8.0+ review score
Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 24 reviews

Offering a garden and lake view, B&B Il Rosmarino is located in Cortona, 37 km from Terme di Montepulciano and 48 km from Perugia Train Station.

From US$200.23 per night

Enjoy breakfast in Cortona and nearby

Scored out of 10, guest rating 7.9
Good - What previous guests thought, 68 reviews

Nestled amid the hills on the Umbria - Tuscany border, the farm house is immersed in nature, just 6 km away from the historic town of Cortona.

From US$208.48 per night
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 62 reviews

Set within 23 km of Piazza Grande and 42 km of Terme di Montepulciano, Agriturismo Borgo tra gli Olivi offers rooms with air conditioning and a private bathroom in Castiglion Fiorentino.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 55 reviews

Featuring free WiFi, parking on-site and an infinity pool, the recently renovated property of Agriturismo Annibale, offers accommodation in Tuoro sul Trasimeno, 39 km from Perugia Cathedral and 40 km...

From US$176.68 per night
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 228 reviews

Set within 20 km of Piazza Grande and 44 km of Terme di Montepulciano, San Michele al Castello offers rooms with air conditioning and a private bathroom in Castiglion Fiorentino.

From US$106.01 per night

Casa Annateresa

Cortona
Breakfast options
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 5 reviews

Located in Cortona, 30 km from Piazza Grande and 37 km from Terme di Montepulciano, Casa Annateresa provides accommodation with amenities such as free WiFi and a TV.

Scored out of 10, guest rating 6.7
Pleasant - What previous guests thought, 3 reviews

Appartamento del Capitano is situated in the Cortona Old Town district of Cortona, 48 km from Perugia Train Station, 50 km from Corso Vannucci and 35 km from Magione Motorspeedway.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 34 reviews

Offering city views, Appartamento Il Loggiato is an accommodation located in Cortona, 37 km from Terme di Montepulciano and 48 km from Perugia Train Station.

Raggi di Sole

Cortona
Breakfast options
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 73 reviews

Offering city views, Raggi di Sole is an accommodation located in Cortona, 30 km from Piazza Grande and 37 km from Terme di Montepulciano.

From US$159.25 per night

These holiday rentals in Cortona and nearby have options with free cancellation

L'Antico Lavatoio

Cortona
Free cancellation options available

Set in Cortona, 31 km from Piazza Grande and 37 km from Terme di Montepulciano, L'Antico Lavatoio offers air-conditioned accommodation with a terrace and free WiFi.

From US$193.17 per night

Agriturismo Il Torrino

Cortona
Free cancellation options available
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 7 reviews

Set in Cortona, 31 km from Piazza Grande and 50 km from Perugia Cathedral, Agriturismo Il Torrino offers air conditioning.

From US$270.91 per night

Il Centrale

Cortona
Free cancellation options available
Scored out of 10, guest rating 7.6
Good - What previous guests thought, 221 reviews

Il Centrale is situated in Cortona, 30 km from Piazza Grande, 50 km from Perugia Cathedral, and 50 km from San Severo Church - Perugia.

From US$82.45 per night

Margherita Holiday Home

Cortona
Free cancellation options available
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 53 reviews

Boasting pool with a view and views of pool, Margherita Holiday Home is a farm stay set in a historic building in Cortona, 28 km from Piazza Grande.

From US$179.74 per night

Casa Vacanze Papà Giuseppe

Cortona
Free cancellation options available
Scored out of 10, guest rating 7.2
Good - What previous guests thought, 48 reviews

Casa Vacanze Papà Giuseppe is located in Cortona, 34 km from Piazza Grande, 49 km from Perugia Cathedral, as well as 49 km from San Severo Church - Perugia.

From US$88.34 per night

Casa del Nonno Bingheri

Cortona
Free cancellation options available
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Situated in Cortona, 36 km from Piazza Grande and 49 km from Perugia Cathedral, Casa del Nonno Bingheri offers a garden and air conditioning.

From US$1,705.36 per night

Podere La Vecchia Fornace

Cortona
Free cancellation options available
Scored out of 10, guest rating 7.5
Good - What previous guests thought, 254 reviews

Located in Cortona, in a historic building, 37 km from Piazza Grande, Podere La Vecchia Fornace is an aparthotel with a seasonal outdoor swimming pool and garden.

From US$119.26 per night
Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 1 review

Borgo Dolci Colline Resort Cipresso provides a hot tub and free private parking, and is within 21 km of Piazza Grande and 44 km of Terme di Montepulciano.

From US$214.62 per night

Holiday Rentals with swimming pools in Cortona and nearby

Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 43 reviews

Located in Cortona in the Tuscany region and Piazza Grande reachable within 32 km, Podere Casorbica provides accommodation with free WiFi, a children's playground, pool with a view and free private...

From US$129.56 per night
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 26 reviews

Set just 24 km from Piazza Grande, La Maestà Tuscan Sun provides accommodation in Castiglion Fiorentino with access to a rooftop pool, a garden, as well as luggage storage space.

From US$121.20 per night
Scored out of 10, guest rating 7.5
Good - What previous guests thought, 22 reviews

Boasting pool views, Maine case vacanza features accommodation with patio, around 37 km from Piazza Grande. With mountain views, this accommodation provides a balcony and a swimming pool.

From US$358.30 per night
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 27 reviews

Borgo Sanguineto is situated in Tuoro sul Trasimeno, 39 km from Perugia Cathedral, 40 km from San Severo Church - Perugia, and 43 km from Piazza Grande.

From US$180.92 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

Borgo Dolci Colline Resort Granaio offers a hot tub and free private parking, and is within 21 km of Piazza Grande and 44 km of Terme di Montepulciano.

From US$515.09 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Boasting a year-round outdoor pool, a sauna and a hot tub, Borgo Dolci Colline Resort Loggia is situated in Castiglion Fiorentino, 21 km from Piazza Grande and 44 km from Terme di Montepulciano.

From US$227.63 per night

Villa Chiara

Cortona
Swimming pool
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Set only 32 km from Piazza Grande in Cortona, Villa Chiara offers accommodation fitted with a terrace, garden and seasonal outdoor pool.

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 23 reviews

Situated within 31 km of Piazza Grande and 37 km of Terme di Montepulciano, CORTONA SUITE - THE HOUSE WITH WELL and THE FRESCOS PALACE provides rooms with air conditioning and a private bathroom in...

FAQ about holiday rentals in Cortona

Holiday rentals that guests love in Cortona

See all
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 80 reviews
Christina was very hospitable and we loved the decor, location and history of the old renovated Italian villa, dipped in charm and the sound of a church bell in the distance.
Guest review by
Heather
Family with young children
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 4 reviews
Fantastic small villa for a family of 4 or 2 couples. Very quiet location in the countryside near Cortona with a view on the mountains. Ideal spot to go and check the central part of Tuscany. Villa has a great pool and garden. House is cosy, but has everything you need.
Guest review by
Ben
Family with young children
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 103 reviews
The villa we stayed in was classic and beautiful. Each room had its own bathroom, providing ample space for everyone. The kitchen was well-furnished with all the necessary amenities. The garden was stunning, and there was plenty of parking space.
Guest review by
Fjo
Group
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 111 reviews
We love this beautiful holiday home and the well-maintained gardens in the surroundings. The compound is conveniently located in between several historical cities and towns, and one can park right in front of his house door. Supermarkt is also close by.
Guest review by
Dingnan
Group