List your home
Apply filters
£ to

47 Holiday homes in Cortona

Reset search

Show results on map

Also consider

Coastal Cottages
222 properties
Sardinia
478 properties
Tuscany
3,181 properties
Lake Garda Area
103 properties
Lake Como Area
494 properties
Sicily
634 properties
Rome
2,609 properties
Florence
1,034 properties
Venice, Veneto
588 properties
Amalfi Coast
519 properties
Trapani
429 properties
Sorrento, Campania
354 properties
Lucca
348 properties
Palermo
332 properties
Cortona
302 properties
Cefalu
284 properties
Taormina
236 properties
Massa Lubrense
215 properties
Milan
213 properties
Positano
206 properties

Filters applied: Smokers (47)

47 Results  |  
23 Photos

Villa | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £151 /night

£1052 - £2191 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
The house is ideal for a relaxing, comfortable and romantic. An old farmhouse dating back to 1200 recently renovated very close to monuments, delicious restarants, all the comfort s for your relax  …see more

22 Photos

Villa | 4 Bedrooms | sleeps 8

6 Nights min stay

Add to shortlist

from £83 /night

£579 - £964 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
The villa "Meridiana" is very easy to reach, is settled in the quiet Brolio Tuscany village Villa with private garden and private swimming pool Tennis table in garden. Fenced private garden. Ground floor 2-3 days a week stays the owner in order to take care to the garden and swimming pool.  …see more

23 Photos

Farmhouse | 6 Bedrooms | sleeps 12

2 Nights min stay

Add to shortlist

from £213 /night

£1490 - £2483 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
The location is vry convenient to visit many of the most beautiful location of central Italy, Tuscany and Umbria, still stayng in a relaxing and peaceful country place.Cortona, the awesom art city, made famous also from teh movie "under the Tuscan Sun" is very close  …see more

Featured properties

12 Photos

Villa | 1 Bedroom | sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £51 /night

£351 - £658 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
Swimming pool, beach or lakeside relaxation, air conditioning, car necessary, may take pets - please enquire, Cortona,  …see more

17 Photos

Farmhouse | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £76 /night

£526 - £833 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
Swimming pool, beach or lakeside relaxation, air conditioning, car essential, internet wifi  …see more

17 Photos

Villa | 2 Bedrooms | sleeps 6

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £76 /night

£526 - £833 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • May take pets – please enquire
Swimming pool, beach or lakeside relaxation, air conditioning, car essential, may take pets - please enquire, Cortona, panoramic  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 16

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £188 /night

£1315 - £2191 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Cortona farmhouse,Swimming pool, balcony/terrace, private garden, pets allowed, beach or lakeside relaxation, air conditioning, car essential.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 14

Very Good 4/5 

Min stay varies

Add to shortlist

from £39 /night

£272 - £2191 / week

View

Key info:

  • Nearest beach 150 km
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Villa Giarradea is the perfect choice for all the people want to spend a beautiful vacancy completely immersed in the peace of the Tuscan nature, without give up to the comfort. The Villa is really near to beautiful trekking, but at just 10 minutes by car from Cortona  …see more

7 Photos

Apartment | 1 Bedroom | sleeps 4

Min stay varies

Add to shortlist

from £107 /night

£745 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
'Vecchio Frantoio' is only a five minute drive from the medieval hilltop town of Cortona. The main A1 motorway is a fifteen minute drive from the apartment and the mainline train station is only a five minute drive away.  …see more

21 Photos

Farmhouse | 3 Bedrooms | sleeps 7

7 Nights min stay

Add to shortlist

from £142 /night

£992 - £1488 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Charming country house with private pool to rent at 1 mile from Cortona – sleeps 6+1 From 1200€ to 1800€ a week  …see more

14 Photos

House | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £84 /night

£583 - £742 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Located in the heart of the Tuscan countryside, Borgo di Vagli is a quaint, meticulously restored 14th century Hamlet surrounded by a protected area of olive groves, fruit trees and ancient oaks.  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £63 /night

£437 - £623 / week

View

Key info:

  • Nearest beach 165 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
The apartment Angelo is part of a larger building once an ancient mill which has been carefully restored to the highest standards and transformed into a country residence with 30 apartments enjoying stunning views, immersed in a green setting only 3 km from Cortona.  …see more

14 Photos

Farmhouse | 10 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £48 /night

£333 - £1577 / week

View

Late Deal: save up to €896 (approx. £740)

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
Prestigious country house immersed in the green countryside offers joyful days of rest  …see more

21 Photos

House | 4 Bedrooms | sleeps 10

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £107 /night

£744 - £1405 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Tuscany property in a village with swimming pool and garden close to Cortona , Montepulciano and the Wine valley. one hour from Florence and two hours from Rome.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 15

7 Nights min stay

Add to shortlist

from £284 /night

£1984 - £2893 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Luxurious detached villa with private pool in southern Tuscany near Cortona. Panoramic and quiet location. 5 bedrooms, 11 bed places + 2 double sofa beds. Air conditioning and Wi-fi internet connection.  …see more

21 Photos

Farmhouse | 5 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £201 /night

£1405 - £2852 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This charming Tuscan Farmhouse with a new salt water pool is ideal for family holidays as it is tucked away in a large garden in lovely, unspoilt Southern Tuscany near the Etruscan hill town of Cortona, amongst olive groves and sunflower fields.  …see more

16 Photos

Cottage | 2 Bedrooms | sleeps 5

Short stays welcome

Add to shortlist

from £48 /night

£331 - £496 / week

View

Key info:

  • Nearest beach 10 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Cortona,Panoramic view, close to town, garden, barbecue.  …see more

24 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £67 /night

£463 - £645 / week

View

Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
"Il Villino di Cortona", is a cozy house nestled in the heart of val di chiana: in an area rich in history and cultural attractions. Tuscany holiday house. (exclusive use property, house, pool, garden). The veranda is ideal to enjoy a rich and tasty breakfast, or to immerse yourself in the reading a good book.  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £38 /night

£263 - £526 / week

View

Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Holiday apartment 2 km from Cortona in the country, equipped with every comfort ,silent An excellent base for excursions nearby (Lake Trasimeno, Montepulciano, Pienza, Siena, Gubbio, etc..), from the house you can also put your shoes on and go for a walk in the woods  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £61 /night

£421 - £675 / week

View

Key info:

  • Nearest beach 149 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Old Tuscan farm-houses recently restored. No so far to Cortona, beautiful Etruscan town, is the ideal place for your next holiday; where you can look at art, nature and culture. Internet free in the garden.  …see more

24 Photos

House | 6 Bedrooms | sleeps 10

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £163 /night

£1139 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Nestled in the foothills of Cortona, overlooking the Val di Chiana and Mount Amiata. The perfect base for exploring the beautiful regions of Tuscany and Umbria or simply relaxing, surrounded by nature.  …see more

10 Photos

Farmhouse | 1 Bedroom | sleeps 4

Very Good 4/5 

2 Nights min stay

Add to shortlist

from £53 /night

£368 - £526 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
The apartments is independent, and has beautiful piece of ancient furniture own heating system, some of them have a fire-place.  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £71 /night

£491 - £859 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
2 bedrooms, full kitchen, living room with sofa bed, bathroom with shower.  …see more

10 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

Add to shortlist

from £54 /night

£372 - £654 / week

View

Key info:

  • Nearest beach 140 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Beautifulapartment with swimming pool situated in the vicinity of Cortona, Tuscany.  …see more

22 Photos

Farmhouse | 3 Bedrooms | sleeps 5

Short stays welcome

Add to shortlist

from £151 /night

£1052 - £1315 / week

View

Key info:

  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
trekking strategic point, silent, beautiful country house, stone view walls, Unfortunately is not possible to use BBQ by law during summer season because woods are too near the house...  …see more

16 Photos

Villa | 8 Bedrooms | sleeps 14

Min stay varies

Add to shortlist

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
The villa is composed of 2 buildings. Main building: ground floor: with dining room, kitchen, bathroom and 3 bedrooms. I° floor: with dining room, kitchen, bathroom and 3 bedrooms. II° building: small house with 2 bedrooms, bathrooms, dining room, living room  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 16

Min stay varies

Add to shortlist

from £300 /night

£2100 - £3700 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Villa Ruffignano is a luxury property, recently reconstructed respecting the traditional characteristics combined with the necessities of modern life.  …see more

16 Photos

Villa | 5 Bedrooms | sleeps 12

Min stay varies

Add to shortlist

from £354 /night

£2475 - £3765 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Villa Torre degli Elci is set in the greens of the Tuscan countryside, midst olives and cypress trees and just 4 km from Cortona. The name of the Villa derives from the old sighting tower which has testimonials from 13th and 14th century and which became a monastery  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £506 /night

£3540 - £4685 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
CoCortona Tuscan Villa with pool- rural views and two independent annexes within walking distance of the medieval walled town of Cortona.  …see more

18 Photos

Villa | 6 Bedrooms | sleeps 14

1 night min stay

Add to shortlist

from £169 /night

£1182 - £2067 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Casa Delia is an antique villa which lies at the bottom of a green hill of Cortona in a quiet and panoramic position. The villa is surrounded by a big park, partly shaded by trees, and with its beautiful swimming pool looks onto the Chiana valley and Cortona  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £93 /night

£650 - £1164 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Villa La Fontana is at the heart of prestigious places of historical interest and artistic national and world: ROME, the capital city with all its historical and architectural merit is about u'ora machine, FLORENCE, capital of the Renaissance is about an hour's journey. CORTONA is located just 15 minutes, ORVIETO 30 minutes, 40 min. SIENA, PERUGIA 20 min., Assisi 30 min.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 18

Short stays welcome

Add to shortlist

from £51 /night

£351 - £3873 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
around the Villa La Fontana: The Parco del Trasimeno runs along the perimeter of Trasimeno lake and is the largest regional park in Umbria. The park includes three islands: the largest is Polvese Island, which is under the control of the Province of Perugia. Stunning Luxury villa in walking distance from Cortona  …see more

22 Photos

Apartment | 3 Bedrooms | sleeps 5

2 Nights min stay

Add to shortlist

from £51 /night

£351 - £439 / week

View

Key info:

  • Suitable for over 5s only
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
La Mansarda del Sodo, a top floor apartment in a typical two storey old stone house one kilometer from the ancient Etruscan village of Cortona. We will be happy to provide assistence, a guided tour of this beautiful area or any information needed.  …see more

16 Photos

House | 2 Bedrooms | sleeps 4

2 Nights min stay

Add to shortlist

from £57 /night

£395 - £544 / week

View

Key info:

  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
Accogliente, caratteristica abitazione in pietra, situata nel centro storico della città etrusca di Cortona, celebre per il suo passato che ancora vive tra i suoi vicoli. Base ideale per visitare Arezzo, Montepulciano, Pienza e le suggestive campagne toscane e umbre.  …see more

13 Photos

Farmhouse | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £22 /night

£149 - £1052 / week

View

Key info:

  • Swimming pool
  • Suitable for over 5s only
  • Car essential
  • Pets welcome
  • Private garden
Ca de Carlicchi is a lovingly restored farmhouse in Tuscany, bordering Umbria. We think that quiet and nature are the starting points to find the well-being of body and soul, especially in a world where the old virtue of "being idle" is apparently forgotten. Would you like to take a dive into the pool, sunbathe, or simply read, day dream and relax undisturbed?  …see more

6 Photos

Farmhouse | 2 Bedrooms | sleeps 6

Min stay varies

Add to shortlist

from £63 /night

£439 - £745 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • May take pets – please enquire
case vacanze, casa vacanza, appartamenti, appartamento, studi, studio monolocali turistici, monolocale turistico, case, casa, vista lago, vacanze, vacanza, turismo, campagna toscana cortona mangiare casale camino barbeque relax capodanno  …see more

12 Photos

Apartment | 3 Bedrooms | sleeps 5

3 Nights min stay

Add to shortlist

from £68 /night

£474 - £789 / week

View

Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
This place and the atmosphere will be the ideal ingredients to spend a peaceful and relaxing holiday immersed in the Tuscan countryside and at the same time to visit the most beautiful cities of historical and cultural interest and gastronomic center of Italy.  …see more

12 Photos

Guest house | 2 Bedrooms | sleeps 3

3 Nights min stay

Add to shortlist

from £61 /night

£421 - £701 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
This place and the atmosphere will be the ideal ingredients to spend a peaceful and relaxing holiday immersed in the Tuscan countryside and at the same time to visit the most beautiful cities of historical and cultural interest and gastronomic center of Italy.  …see more

15 Photos

Farmhouse | 5 Bedrooms | sleeps 10

4 Nights min stay

Add to shortlist

from £188 /night

£1315 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Swimming pool
  • Suitable for over 5s only
  • Car advised
  • Pets welcome
  • Private garden
Una dimora immersa nel verde e nel silenzio delle colline toscane, dotata di tutti i comfort, vicinissima alle principali mete turistiche dell'Italia centrale, a due passi dalle fresche acque del lago Trasimeno.  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

Add to shortlist

from £66 /night

£456 - £1039 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
During the day besides going for a swim in the pool, basking in the sun and reading a good book in the shade of a nearby grove, you will be able to take a tour of a our farm consisting of woods, tilled land, lawns, ponds, olive groves, vineyards, vegetable gardens, orchards, a chicken farm and a small flock of sheep.  …see more

18 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £50 /night

£350 / week

View

Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
L'arredo della casa è semplice, per non alterare l'atmosfera delle antiche case di campagna, ma molto curato. Gode di due giardini privati, uno sul davanti, di circa 400 metri quadri con una pergola e un antico forno a legna, l'altro sul retro di circa 1000 metriquadri. Parcheggio privato. La struttura è adatta a famiglie con bambini ai quali possono essere forniti lettini.  …see more

18 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

Add to shortlist

from £36 /night

£250 - £386 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
La splendida vista della dolce collina cortonese, il tranquillo parco e la quiete della campagna della Val di Chiana vi permetteranno di apprezzare l'armonia del vostro “nido” di vacanza. Il nido è, per noi, simbolo di dimora accogliente.  …see more

14 Photos

Apartment | 2 Bedrooms | sleeps 3

7 Nights min stay

Add to shortlist

from £82 /night

£570 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
La sua posizione strategica permette agli ospiti di assaporare appieno la tranquillità della vita di campagna e di raggiungere facilmente centri storici ed artistici dell'Italia centrale.  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

Add to shortlist

from £36 /night

£250 - £386 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
  • Private garden
La villa di campagna “I Nidi di Cortona” è situata in campagna, presso il piccolo borgo rurale di San Marco in Villa (sec. XIV), ai piedi della collina su cui si distende la cittadina etrusca di Cortona.  …see more

15 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

Add to shortlist

from £56 /night

£386 - £570 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
L'edificio è circondato da un parco attrezzato con panchine, sdraio, dondolo, amaca ed illuminazione esterna. Tra abeti, cipressi ed altri alberi d'alto fusto nidificano varie specie d'uccelli che col loro cinguettio animano la quiete circostante.  …see more

18 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

Add to shortlist

from £36 /night

£250 - £386 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
La sua posizione strategica permette agli ospiti di assaporare appieno la tranquillità della vita di campagna e di raggiungere facilmente centri storici ed artistici dell'Italia centrale. “I Nidi di Cortona” è punto di partenza ideale per escursioni.  …see more

12 Photos

House | 6 Bedrooms | sleeps 12

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £126 /night

£877 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • May take pets – please enquire
  • Private garden
-  …see more