List your home
Apply filters
£ to

368 Holiday homes in Cortona

Reset search

Show results on map

Filter your search

Price per night

£ to

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Province of Arezzo Clear
  • Cortona Clear
  • All locations
  • Bagnolo (11)
  • Capezzine (2)
  • Cegliolo (6)
  • Centoia (9)
  • Farinaio (2)
  • Fratta Sant'Agata (2)
  • Fratta Santa Caterina (9)
  • Fratticciola (4)
  • Localita Mucchia (4)
  • Mercatale di Cortona (20)
  • Montalla (7)
  • Montanare (6)
  • Montecchio, San Lorenzo (5)
  • Poggioni (4)
  • Ruffignano (2)
  • Teverina (2)

more +

less -

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
4,149 properties
Florence
1,420 properties
Milan
503 properties
Cefalu
393 properties
Catania
354 properties
Naples
303 properties
Ostuni
294 properties
Venice
245 properties
Noto
240 properties
Montaione
237 properties
Turin
220 properties
Bologna
183 properties
Praiano
180 properties
Sciacca
159 properties
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
368 Results  |  
21 Photos

Condo | 1 Bedroom | sleeps 4

Excellent 5/5 

1 night min stay

Add to shortlist

from £22 /night

£153 - £240 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Some pets are welcome - please contact the owner
* air conditioning and heating included in price * washer located in bathroom * fully equipped kitchen * wireless internet * outdoor dining on private terrace * private parking space in front of condo * within walking distance to train station and bus stop provided: * towels & linens * bath, dish & laundry soap * paper towels & toilet tissue * hair dryer  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £335 /night

£2339 - £3428 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Stunning Luxury villa in walking distance from Cortona, the famous and well know medieval village thanks to the "under the Tuscan sun" book and movie.  …see more

21 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £85 /night

£593 - £783 / week

View

Key info:

  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Charming small villa near Cortona, large gardens and olive grove with views of the surrounding hills. A/C and Wi-Fi throughout. The perfect base to explore Tuscany and Umbria. Very comfortable, fully equipped. Stunning countryside. Free GPS, Italian cell phone,laptop. Swimming pools/thermal spas. Great restaurants. Short walk to village.  …see more

Featured properties

23 Photos

Villa | 10 Bedrooms | sleeps 20

1 night min stay

Add to shortlist

from £553 /night

£3871 - £5184 / week

View

Key info:

  • Nearest beach 2 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Villa Under the Tuscan Sun walk to Town of Cortona. Amaziong view, beautiful swimming pool and tennis Court for exclusive use.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £248 /night

£1732 - £2142 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Pets welcome
  • Private garden
Villa in Cortona with 3 bedrooms sleeps 6  …see more

11 Photos

Villa | 4 Bedrooms | sleeps 8

Short stays welcome

Add to shortlist

from £328 /night

£2295 - £4195 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Fonte Vecchia is Situated Deep in the Heart of Piero della Francesca Country in the Niccone Valley and is rated one of the top 15 villas to stay in Italy  …see more

26 Photos

Farmhouse | 6 Bedrooms | sleeps 12

2 Nights min stay

Add to shortlist

from £196 /night

£1371 - £2255 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • 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

27 Photos

Villa | 6 Bedrooms | sleeps 15

7 Nights min stay

Add to shortlist

from £420 /night

£2936 - £4421 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This incredible structure offers to its guests two different accommodations completely independent : the Villa and the cottage.  …see more

22 Photos

Farmhouse | 12 Bedrooms | sleeps 22

2 Nights min stay

Add to shortlist

from £369 /night

£2581 - £4113 / week

View

Key info:

  • Nearest beach 12 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Cuiano is a sprawling farmhouse with marvelous panoramic views of the Niccone Valley and the mountains of Umbria. The farmhouse has been divided in self-cointained apartments, that possible to rent separated too. Four fireplaces in flats and pizza oven outdoor. Villa with Pool, Terrace, Cook service, Playground, BBQ: sleeps 2 to 24 in 6 flat renting separated too.  …see more

22 Photos

Villa | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £88 /night

£614 - £1009 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
The Orangery, charming villa with private swimming pool is placed in the magnificent Tuscan countryside, surrounded by olive trees and vineyard: the perfect setting in an atmosphere of complete relaxation and comfort but also only 400 mt far from the stunning Cortona  …see more

16 Photos

Villa | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £149 /night

£1041 - £1734 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
3 bedrooms Tuscan country villa in panoramic location with private swimming pool , private garden and parking . Five minutes away from the beautiful medieval city of Cortona and the famous cooking school I Gustasapori  …see more

17 Photos

Villa | 4 Bedrooms | sleeps 8

6 Nights min stay

Add to shortlist

from £315 /night

£2200 - £3200 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa San Martino offers not just another holiday in Tuscany or Umbria; this is a really special place. The villa is beautifully presented and has an exquisite pool with spectacular views across the famous Niccone Valley towards Mercatale di Cortona. Only 15 minutes from the villa you can easily access the Etruscan town of Cortona.  …see more

22 Photos

Farmhouse | 3 Bedrooms | sleeps 5

Short stays welcome

Add to shortlist

from £81 /night

£565 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • 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

23 Photos

Villa | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £150 /night

£1049 - £2017 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • 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

11 Photos

Villa | 2 Bedrooms | sleeps 5

7 Nights min stay

Add to shortlist

from £93 /night

£646 - £1291 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
This lovely small villa is located at 400 m from the charming town of Cortona It is situated in a wonderful panoramic position, surrounded by the typical Tuscan countryside and olive groves, in a perfect location for a lovely and relaxing holiday, yet with the advanta  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £99 /night

£688 - £1185 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
The beautifully decorated Tuscan-villino is surrounded by cypresses, old pines and olive trees, the residences offer magnificent views of the enchanting Valdichiana, a rolling countryside of sunflowers and vineyards. Excellent Restaurant by the pool .  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

Add to shortlist

from £75 /night

£525 / week

View

Key info:

  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
Casina via Iannelli offers you the opportunity to stay in the historic center of Cortona in a house of historical and artistic interest created and preserved until the beginning of 1300.  …see more

17 Photos

Apartment | 2 Bedrooms | sleeps 4

Short stays welcome

Add to shortlist

from £47 /night

£323 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
Elegantly furnished apartment a few meters away from the main sites of the city. At 50 meters from the apartment you will find the public parking where you can leave your car.  …see more

22 Photos

Villa | 4 Bedrooms | sleeps 6

6 Nights min stay

Add to shortlist

from £77 /night

£533 - £888 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great 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

6 Photos

Guest house | 6 Bedrooms | sleeps 25

1 night min stay

Add to shortlist

from £74 /night

£517 - £807 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
La Fiorita is a farmhouse nestled in the beautiful Tuscan countryside, on the border between the provinces of Arezzo and Siena.  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 10

1 night min stay

Add to shortlist

from £173 /night

£1210 - £2541 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Villa La Pergola is an authentic private villa in Tuscany, very close to the Etruscan town of Cortona. La Pergola is situated in a cosy village consisting of two other villas each with private swimming pool.  …see more

14 Photos

Apartment | 2 Bedrooms | sleeps 4

4 Nights min stay

Add to shortlist

from £71 /night

£495 - £1050 / week

View

Key info:

  • Nearest beach 12 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
On the Tuscany / Umbria border, the old farm of Azienda Pilari is only a short drive to Cortona and Lake Trasimeno. A walk across the field takes you to an old market town with a few shops, bars and restaurants Wine and olive oil produced on the farm are available for purchase.  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £125 /night

£871 - £1573 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
cortona farmhouse agriturismo  …see more

15 Photos

Cottage | 1 Bedroom | sleeps 2

4 Nights min stay

Add to shortlist

from £58 /night

£404 - £505 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Car advised
  • No pets allowed
Character detached chestnut beamed cottage just below Cortona with terracotta tiles to sleep two with shared pool.  …see more

14 Photos

Villa | 5 Bedrooms | sleeps 10

4 Nights min stay

Add to shortlist

from £162 /night

£1130 - £1412 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
IL CASALE DI CARMINA is the place for those who love nature and tranquility of the Tuscan hills.  …see more

23 Photos

Cottage | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £87 /night

£609 - £1433 / week

View

Key info:

  • Nearest beach 25 km
  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Beautiful 2 bedroom cottage with the most stunning views Pool and Wifi. Close to villages. Niccone Valley, ideally situated for a relaxing family holiday and for seeing Umbria and Tuscany. Baby-sitters or cooks can be available on request for an additional cost.  …see more

24 Photos

Lodge | 1 Bedroom | sleeps 4

2 Nights min stay

Add to shortlist

from £52 /night

£363 - £557 / week

View

Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Fattoria Borgonuovo - La Rosa Charming indipendent apartment, 60 square meters, ground floor with an outside area and an outdoor swimmingpool (6x12m). The owners speak and understand fluent English.  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 8

1 night min stay

Add to shortlist

from £277 /night

£1936 - £2517 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Bella is a stunning, luxury villa nestled in the Valdichiana valley just a few kilometres from Cortona. An ideal destination for exploring the beautiful regions of Tuscany and Umbria.  …see more

24 Photos

Villa | 7 Bedrooms | sleeps 14

1 night min stay

Add to shortlist

from £277 /night

£1936 - £2541 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Recently restored Tuscan Villa with traditional Terracotta tiled floors, plunged in the greenery of southern Tuscany.  …see more

24 Photos

Studio | sleeps 2

2 Nights min stay

Add to shortlist

from £48 /night

£330 - £411 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Casale Il Granaio is in a evocative hamlet in the countryside, in the heart of Valdichiana, bordering on Umbria, a few km from Trasimeno Lake. The former Tavern of the property is nowadays a studio-flat offering exposed-beam ceilings and wooden furnishings, suitable for  …see more

18 Photos

Hotel apartment | 2 Bedrooms | sleeps 5

2 Nights min stay

Add to shortlist

from £91 /night

£633 - £1011 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
  • Private garden
Residence in Cortona with 2 bedrooms sleeps 5  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 10

1 night min stay

Add to shortlist

from £173 /night

£1210 - £2259 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Teresa, Distinguished Panoramic Villa Overlooking a Breathtaking Landscape  …see more

12 Photos

Cottage | 5 Bedrooms | sleeps 10

1 night min stay

Add to shortlist

from £173 /night

£1210 - £2017 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Stone cottage in a wonderful hilly position, just a few minutes from the medieval town of Cortona. Gorgeous panoramic view from the private pool, and beautiful walks to explore including the ancient Roman road. Dip into the magical peace of the Tuscan countryside.  …see more

19 Photos

Apartment | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £68 /night

£470 - £610 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Holiday apartments near Cortona in Tuscany. These self-contained apartments have a large pool, BBQ and Picnic area. There is ample parking space and the surrounding gardens are particularly beautiful, with colour and scent from the many rose bushes, jasmine & lavender. We can arrange special days or tours such as; Wine Tasting Cooking Cycling Painting Walking Weddings  …see more

20 Photos

Hotel apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

Add to shortlist

from £91 /night

£633 - £1011 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Residence in Cortona with 2 bedrooms sleeps 4  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

Add to shortlist

from £70 /night

£484 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 20 km
  • Ask owner if suitable for children
  • Car not necessary
  • No pets allowed
Central apartment in the heart of Cortona, Tuscany, ideal for two person elegant and quiet, near the best restaurant and grocery, shops and free parking. A perfect place to visiting Cortona and Tuscany tow like Arezzo, Siena, Firenze, Pienza, valdorcia, San Gimignano. Only 3 minute from main square and grocery, and just 4 minutes walk from public free and safe parking.  …see more

24 Photos

Villa | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £84 /night

£587 - £889 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Pets welcome
  • Private garden
Villa in Cortona with 1 bedrooms sleeps 2  …see more

24 Photos

Villa | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £84 /night

£587 - £889 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
Villa in Cortona with 1 bedrooms sleeps 2  …see more

20 Photos

Hotel apartment | 1 Bedroom | sleeps 3

2 Nights min stay

Add to shortlist

from £83 /night

£578 - £889 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Residence in Cortona with 1 bedrooms sleeps 3  …see more

24 Photos

Hotel apartment | 1 Bedroom | sleeps 2

2 Nights min stay

Add to shortlist

from £82 /night

£568 - £842 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
  • Private garden
Residence in Cortona with 1 bedrooms sleeps 2  …see more

24 Photos

Hotel apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

Add to shortlist

from £91 /night

£633 - £1011 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Residence in Cortona with 2 bedrooms sleeps 4  …see more

18 Photos

Hotel apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

Add to shortlist

from £91 /night

£633 - £1011 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Residence in Cortona with 2 bedrooms sleeps 4  …see more

24 Photos

Hotel apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

Add to shortlist

from £91 /night

£633 - £1011 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Residence in Cortona with 2 bedrooms sleeps 4  …see more

24 Photos

Hotel apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

Add to shortlist

from £91 /night

£633 - £1011 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Residence in Cortona with 2 bedrooms sleeps 4  …see more

24 Photos

Hotel apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

Add to shortlist

from £91 /night

£633 - £1011 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Residence in Cortona with 2 bedrooms sleeps 4  …see more

18 Photos

Hotel apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

Add to shortlist

from £91 /night

£633 - £1011 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
Residence in Cortona with 2 bedrooms sleeps 4  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £35 /night

£242 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
The apartment Sant'Angelo is located just below the Etruscan City of Cortona in a beautiful residential complex which has been tastefully restored, maintaining the traditional characteristics of the antique oil mill that it once was. Video footage of apartment on Youtube is available on:http://youtu.be/wR2cgZSvDOM  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £73 /night

£508 - £795 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
La Fiorita is a farmhouse nestled in the beautiful Tuscan countryside. From every corner of the estate you have magnificent views of bucolic flavor with wide open spaces overlooking the hills of Montepulciano and Cortona  …see more

21 Photos

Apartment | 3 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £100 /night

£696 - £1129 / week

View

Key info:

  • Nearest beach 200 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Private independent accommodation with private garden area, private parking and independent entrance. The shared swimming pool area is very large and used from no more than 3 family at the time.  …see more

24 Photos

Studio | sleeps 4

1 night min stay

Add to shortlist

from £47 /night

£323 - £444 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
Cozy, spacious, clean, comfortable, canopy bed, fireplace, kitchen, bathroom, wifi  …see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page