We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Cortona

Where to?
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Neighbourhood

Distance from

1 km
1138 rentals in Cortona.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
villa ai cedri, holiday rental in Cortona
villa ai cedri, holiday rental in Cortona
villa ai cedri, holiday rental in Cortona

villa ai cedri

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

La Terrazza sulla Valle, holiday rental in Cortona
La Terrazza sulla Valle, holiday rental in Cortona
La Terrazza sulla Valle, holiday rental in Cortona

La Terrazza sulla Valle

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Casa del Balestriere In Centro Storico , holiday rental in Cortona
Casa del Balestriere In Centro Storico , holiday rental in Cortona
Casa del Balestriere In Centro Storico , holiday rental in Cortona

Casa del Balestriere In Centro Storico

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Casa Dolce Vita: refined apartment in Cortona, holiday rental in Cortona
Casa Dolce Vita: refined apartment in Cortona, holiday rental in Cortona
Casa Dolce Vita: refined apartment in Cortona, holiday rental in Cortona

Casa Dolce Vita: refined apartment in Cortona

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Casa Contea Il Leccio Cortona swim-pool, holiday rental in Cortona
Casa Contea Il Leccio Cortona swim-pool, holiday rental in Cortona
Casa Contea Il Leccio Cortona swim-pool, holiday rental in Cortona

Casa Contea Il Leccio Cortona swim-pool

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Charming small villa near Cortona,garden,olive grove.A/C.Free Wifi - LA COLONICA, holiday rental in Cortona
Charming small villa near Cortona,garden,olive grove.A/C.Free Wifi - LA COLONICA, holiday rental in Cortona
Charming small villa near Cortona,garden,olive grove.A/C.Free Wifi - LA COLONICA, holiday rental in Cortona

Charming small villa near Cortona,garden,olive grove.A/C.Free Wifi - LA COLONICA

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Villino Cortona - Holiday home with private pool, wifi, a/c, based in Tuscany, holiday rental in Cortona
Villino Cortona - Holiday home with private pool, wifi, a/c, based in Tuscany, holiday rental in Cortona
Villino Cortona - Holiday home with private pool, wifi, a/c, based in Tuscany, holiday rental in Cortona

Villino Cortona - Holiday home with private pool, wifi, a/c, based in Tuscany

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Borgo Valecchie, Exclusive Villa set with private pool, Cortona, Tuscany , holiday rental in Cortona
Borgo Valecchie, Exclusive Villa set with private pool, Cortona, Tuscany , holiday rental in Cortona
Borgo Valecchie, Exclusive Villa set with private pool, Cortona, Tuscany , holiday rental in Cortona

Borgo Valecchie, Exclusive Villa set with private pool, Cortona, Tuscany

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

"Villa Stefania" Old  Tuscan Farmhouse - Great View on Cortona, holiday rental in Cortona
"Villa Stefania" Old  Tuscan Farmhouse - Great View on Cortona, holiday rental in Cortona
"Villa Stefania" Old  Tuscan Farmhouse - Great View on Cortona, holiday rental in Cortona

"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

To Stones, holiday rental in Cortona
To Stones, holiday rental in Cortona
To Stones, holiday rental in Cortona

To Stones

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

City / Village Apartment in Cortona with 2 bedrooms sleeps 4, holiday rental in Cortona
City / Village Apartment in Cortona with 2 bedrooms sleeps 4, holiday rental in Cortona
City / Village Apartment in Cortona with 2 bedrooms sleeps 4, holiday rental in Cortona

City / Village Apartment in Cortona with 2 bedrooms sleeps 4

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Casa Mia a CORTONA: Overlook Valdichiana & Tuscany, holiday rental in Cortona
Casa Mia a CORTONA: Overlook Valdichiana & Tuscany, holiday rental in Cortona
Casa Mia a CORTONA: Overlook Valdichiana & Tuscany, holiday rental in Cortona

Casa Mia a CORTONA: Overlook Valdichiana & Tuscany

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Il Roseto - Special prices for 2022-23! !  Get a quote ! !  "Plan your dream", holiday rental in Cortona
Il Roseto - Special prices for 2022-23! !  Get a quote ! !  "Plan your dream", holiday rental in Cortona
Il Roseto - Special prices for 2022-23! !  Get a quote ! !  "Plan your dream", holiday rental in Cortona

Il Roseto - Special prices for 2022-23! ! Get a quote ! ! "Plan your dream"

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Under the Tuscan Sun, holiday rental in Cortona
Under the Tuscan Sun, holiday rental in Cortona
Under the Tuscan Sun, holiday rental in Cortona

Under the Tuscan Sun

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

CHARMING COTTAGE NEAR CORTONA, GARDEN, DINING PATIO, OLIVE GROVE, AC,WiFI , holiday rental in Cortona
CHARMING COTTAGE NEAR CORTONA, GARDEN, DINING PATIO, OLIVE GROVE, AC,WiFI , holiday rental in Cortona
CHARMING COTTAGE NEAR CORTONA, GARDEN, DINING PATIO, OLIVE GROVE, AC,WiFI , holiday rental in Cortona

CHARMING COTTAGE NEAR CORTONA, GARDEN, DINING PATIO, OLIVE GROVE, AC,WiFI

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Luxury Peaceful Villa With Vine Covered Pergola Enjoying Panoramic Views., holiday rental in Cortona
Luxury Peaceful Villa With Vine Covered Pergola Enjoying Panoramic Views., holiday rental in Cortona
Luxury Peaceful Villa With Vine Covered Pergola Enjoying Panoramic Views., holiday rental in Cortona

Luxury Peaceful Villa With Vine Covered Pergola Enjoying Panoramic Views.

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out

Villa Nobile, holiday rental in Cortona
Villa Nobile, holiday rental in Cortona
Villa Nobile, holiday rental in Cortona

Villa Nobile

Holiday Rental House
9 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Sun-Soaked Private View Terrace in the Historical Centre of Cortona., holiday rental in Cortona
Sun-Soaked Private View Terrace in the Historical Centre of Cortona., holiday rental in Cortona
Sun-Soaked Private View Terrace in the Historical Centre of Cortona., holiday rental in Cortona

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Charming apartment located in historic centre of Cortona, WiFi, Air/Con, 2 baths, holiday rental in Cortona
Charming apartment located in historic centre of Cortona, WiFi, Air/Con, 2 baths, holiday rental in Cortona
Charming apartment located in historic centre of Cortona, WiFi, Air/Con, 2 baths, holiday rental in Cortona

Charming apartment located in historic centre of Cortona, WiFi, Air/Con, 2 baths

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Apartment in Cortona with 1 bedrooms sleeps 4, holiday rental in Cortona
Apartment in Cortona with 1 bedrooms sleeps 4, holiday rental in Cortona
Apartment in Cortona with 1 bedrooms sleeps 4, holiday rental in Cortona

Apartment in Cortona with 1 bedrooms sleeps 4

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool, holiday rental in Cortona
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool, holiday rental in Cortona
Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool, holiday rental in Cortona

Luxury Cortona view hilltop Villa,great for families/groups; A/C & heatable pool

Holiday Rental House
6 bedrooms
9 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Bed & Breakfast in Cortona with 2 bedrooms sleeps 4, holiday rental in Cortona
Bed & Breakfast in Cortona with 2 bedrooms sleeps 4, holiday rental in Cortona
Bed & Breakfast in Cortona with 2 bedrooms sleeps 4, holiday rental in Cortona

Bed & Breakfast in Cortona with 2 bedrooms sleeps 4

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Beautiful villa with spectacular views in a rural location, holiday rental in Cortona
Beautiful villa with spectacular views in a rural location, holiday rental in Cortona
Beautiful villa with spectacular views in a rural location, holiday rental in Cortona

Beautiful villa with spectacular views in a rural location

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Stunning Tuscan villa with five bedrooms near Cortona, private pool and Wi-Fi!, holiday rental in Cortona
Stunning Tuscan villa with five bedrooms near Cortona, private pool and Wi-Fi!, holiday rental in Cortona
Stunning Tuscan villa with five bedrooms near Cortona, private pool and Wi-Fi!, holiday rental in Cortona

Stunning Tuscan villa with five bedrooms near Cortona, private pool and Wi-Fi!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Cortona Charme - La Terrazza Cortonese, holiday rental in Cortona
Cortona Charme - La Terrazza Cortonese, holiday rental in Cortona
Cortona Charme - La Terrazza Cortonese, holiday rental in Cortona

Cortona Charme - La Terrazza Cortonese

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Vasciano - lovely old farmhouse, stunning views, Tuscany/Umbria border, holiday rental in Cortona
Vasciano - lovely old farmhouse, stunning views, Tuscany/Umbria border, holiday rental in Cortona
Vasciano - lovely old farmhouse, stunning views, Tuscany/Umbria border, holiday rental in Cortona

Vasciano - lovely old farmhouse, stunning views, Tuscany/Umbria border

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out

Villa in Cortona with 2 bedrooms sleeps 6, holiday rental in Cortona
Villa in Cortona with 2 bedrooms sleeps 6, holiday rental in Cortona
Villa in Cortona with 2 bedrooms sleeps 6, holiday rental in Cortona

Villa in Cortona with 2 bedrooms sleeps 6

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Independent Accommodation in Villa with Private Pool and uninterrupted views, holiday rental in Cortona
Independent Accommodation in Villa with Private Pool and uninterrupted views, holiday rental in Cortona
Independent Accommodation in Villa with Private Pool and uninterrupted views, holiday rental in Cortona

Independent Accommodation in Villa with Private Pool and uninterrupted views

Condo/Apartment
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Bed & Breakfast in Cortona with 1 bedrooms sleeps 2, holiday rental in Cortona
Bed & Breakfast in Cortona with 1 bedrooms sleeps 2, holiday rental in Cortona
Bed & Breakfast in Cortona with 1 bedrooms sleeps 2, holiday rental in Cortona

Bed & Breakfast in Cortona with 1 bedrooms sleeps 2

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Borgo di Vagli, holiday rental in Cortona
Borgo di Vagli, holiday rental in Cortona
Borgo di Vagli, holiday rental in Cortona

Borgo di Vagli

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Villa Mulinoavento with magnificent view 5 minutes walking downtown, holiday rental in Cortona
Villa Mulinoavento with magnificent view 5 minutes walking downtown, holiday rental in Cortona
Villa Mulinoavento with magnificent view 5 minutes walking downtown, holiday rental in Cortona

Villa Mulinoavento with magnificent view 5 minutes walking downtown

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Six bedroom traditional Tuscan villa 5 minutes’ walking distance to Cortona!, holiday rental in Cortona
Six bedroom traditional Tuscan villa 5 minutes’ walking distance to Cortona!, holiday rental in Cortona
Six bedroom traditional Tuscan villa 5 minutes’ walking distance to Cortona!, holiday rental in Cortona

Six bedroom traditional Tuscan villa 5 minutes’ walking distance to Cortona!

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out

Under the Tuscan sun: at Casa Mia A Cortona!, holiday rental in Cortona
Under the Tuscan sun: at Casa Mia A Cortona!, holiday rental in Cortona
Under the Tuscan sun: at Casa Mia A Cortona!, holiday rental in Cortona

Under the Tuscan sun: at Casa Mia A Cortona!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

Typical house with private pool and a stunning view, holiday rental in Cortona
Typical house with private pool and a stunning view, holiday rental in Cortona
Typical house with private pool and a stunning view, holiday rental in Cortona

Typical house with private pool and a stunning view

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

Vacatoin Rentals at Le Celle Del Farinaio in Short, holiday rental in Cortona
Vacatoin Rentals at Le Celle Del Farinaio in Short, holiday rental in Cortona
Vacatoin Rentals at Le Celle Del Farinaio in Short, holiday rental in Cortona

Vacatoin Rentals at Le Celle Del Farinaio in Short

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Set in the majestic Tuscan hills, six bedroom farmhouse with outdoor pool, private garden and gorgeous views, holiday rental in Cortona
Set in the majestic Tuscan hills, six bedroom farmhouse with outdoor pool, private garden and gorgeous views, holiday rental in Cortona
Set in the majestic Tuscan hills, six bedroom farmhouse with outdoor pool, private garden and gorgeous views, holiday rental in Cortona

Set in the majestic Tuscan hills, six bedroom farmhouse with outdoor pool, private garden and gorgeous views

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

THE HOUSE OF GRANDPARENTS, holiday rental in Cortona
THE HOUSE OF GRANDPARENTS, holiday rental in Cortona
THE HOUSE OF GRANDPARENTS, holiday rental in Cortona

THE HOUSE OF GRANDPARENTS

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Private Villa with WIFI, A/C, private pool, TV, patio, pets allowed, panoramic, holiday rental in Cortona
Private Villa with WIFI, A/C, private pool, TV, patio, pets allowed, panoramic, holiday rental in Cortona
Private Villa with WIFI, A/C, private pool, TV, patio, pets allowed, panoramic, holiday rental in Cortona

Private Villa with WIFI, A/C, private pool, TV, patio, pets allowed, panoramic

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Super Panoramic Private Terrace in the Historical Centre of Cortona, holiday rental in Cortona
Super Panoramic Private Terrace in the Historical Centre of Cortona, holiday rental in Cortona
Super Panoramic Private Terrace in the Historical Centre of Cortona, holiday rental in Cortona

Super Panoramic Private Terrace in the Historical Centre of Cortona

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Villa Ivana - Exclusive Luxury Tuscan Villa in Cortona - Italy, holiday rental in Cortona
Villa Ivana - Exclusive Luxury Tuscan Villa in Cortona - Italy, holiday rental in Cortona
Villa Ivana - Exclusive Luxury Tuscan Villa in Cortona - Italy, holiday rental in Cortona

Villa Ivana - Exclusive Luxury Tuscan Villa in Cortona - Italy

Holiday Rental House
9 bedrooms
12 bathrooms
Sleeps 18
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Villa Diana's Garden, holiday rental in Cortona
Villa Diana's Garden, holiday rental in Cortona
Villa Diana's Garden, holiday rental in Cortona

Villa Diana's Garden

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Built in 1251 yet totally remodeled in 2014- Located in Historic Cortona City, holiday rental in Cortona
Built in 1251 yet totally remodeled in 2014- Located in Historic Cortona City, holiday rental in Cortona
Built in 1251 yet totally remodeled in 2014- Located in Historic Cortona City, holiday rental in Cortona

Built in 1251 yet totally remodeled in 2014- Located in Historic Cortona City

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out

Romantic Suite Caminetto, holiday rental in Cortona
Romantic Suite Caminetto, holiday rental in Cortona
Romantic Suite Caminetto, holiday rental in Cortona

Romantic Suite Caminetto

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out

Casa Rina Cortona with large pool, large private terrace, beautiful views, WiFi, holiday rental in Cortona
Casa Rina Cortona with large pool, large private terrace, beautiful views, WiFi, holiday rental in Cortona
Casa Rina Cortona with large pool, large private terrace, beautiful views, WiFi, holiday rental in Cortona

Casa Rina Cortona with large pool, large private terrace, beautiful views, WiFi

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out

Villa in Il Castagno with 3 bedrooms sleeps 8, holiday rental in Cortona
Villa in Il Castagno with 3 bedrooms sleeps 8, holiday rental in Cortona
Villa in Il Castagno with 3 bedrooms sleeps 8, holiday rental in Cortona

Villa in Il Castagno with 3 bedrooms sleeps 8

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out

La Finestra sul Teatro, holiday rental in Cortona
La Finestra sul Teatro, holiday rental in Cortona
La Finestra sul Teatro, holiday rental in Cortona

La Finestra sul Teatro

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out

Apartment 'Leonardo'in cortona's country (2bd), holiday rental in Cortona
Apartment 'Leonardo'in cortona's country (2bd), holiday rental in Cortona
Apartment 'Leonardo'in cortona's country (2bd), holiday rental in Cortona

Apartment 'Leonardo'in cortona's country (2bd)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Gorgeous Comfortable House with Garden & Pool - Its all yours., holiday rental in Cortona
Gorgeous Comfortable House with Garden & Pool - Its all yours., holiday rental in Cortona
Gorgeous Comfortable House with Garden & Pool - Its all yours., holiday rental in Cortona

Gorgeous Comfortable House with Garden & Pool - Its all yours.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out

Stefy apartment, Cortona, holiday rental in Cortona
Stefy apartment, Cortona, holiday rental in Cortona
Stefy apartment, Cortona, holiday rental in Cortona

Stefy apartment, Cortona

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check-in
Check-out

Villa at the Foot of Cortona in Tuscany, holiday rental in Cortona
Villa at the Foot of Cortona in Tuscany, holiday rental in Cortona
Villa at the Foot of Cortona in Tuscany, holiday rental in Cortona

Villa at the Foot of Cortona in Tuscany

Holiday Rental House
9 bedrooms
8 bathrooms
Sleeps 18
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Showing results 1-50 of 1,138
Frequently Asked Questions about Cortona