List your home
Apply filters
£ to

144 Holiday homes in Cortona

Reset search

Show results on map

Filter your search

Price per day

£ to

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Arezzo Province Clear
  • Cortona Clear
  • All suburbs
  • Bagnolo (1)
  • Cegliolo (1)
  • Centoia (3)
  • Cignano (17)
  • Fratta Santa Caterina (1)
  • Fratticciola (10)
  • Mercatale di Cortona (6)
  • Montalla (1)
  • Montanare (1)
  • Montecchio, San Lorenzo (2)
  • Poggioni (1)
  • Ruffignano (1)
  • San Pietro a Cegliolo (19)
  • Terontola (6)

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
2,492 properties
Florence
966 properties
Trapani
516 properties
Venice, Veneto
500 properties
Amalfi Coast
463 properties
Lucca
431 properties
Cortona
430 properties
Palermo
401 properties
Sorrento, Campania
353 properties
Cefalu
317 properties
San Gimignano
297 properties
Taormina
271 properties
Greve in Chianti
268 properties
Syracuse
257 properties

Filters applied: Smokers (144)

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
144 Results  |  
24 Photos

Farmhouse | 5 Bedrooms | sleeps 16

Excellent 5/5 

1 night min stay

Add to shortlist

from £206 /night

£1442 - £2544 / 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. Montepulciano, Perugia, Siena, Tuoro, Pienza, Passignano, Firenze, Florence, Relax, piscina, pizza even, garden, pisa, roma  …see more

23 Photos

Farmhouse | 10 Bedrooms | sleeps 10

2 Nights min stay

Add to shortlist

from £47 /night

£323 - £1527 / week

View

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. It is located in the immediate vicinity of the town of Cortona. Ralaxation room, games and reading area Private and secure parking Swimming pool BBQ Area  …see more

14 Photos

House | 2 Bedrooms | sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £84 /night

£583 - £848 / 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

Featured properties

12 Photos

Farmhouse | 4 Bedrooms | sleeps 6

2 Nights min stay

Add to shortlist

from £68 /night

£475 - £832 / 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

23 Photos

Villa | 3 Bedrooms | sleeps 6

1 night min stay

Add to shortlist

from £158 /night

£1103 - £2120 / 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

Farmhouse | 3 Bedrooms | sleeps 5

Short stays welcome

Add to shortlist

from £110 /night

£764 - £806 / week

View

Key info:

  • Suitable for children of all ages
  • 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

10 Photos

Farmhouse | 1 Bedroom | sleeps 4

Very Good 4/5 

2 Nights min stay

Add to shortlist

from £51 /night

£357 - £509 / 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

17 Photos

Farmhouse | 2 Bedrooms | sleeps 6

Excellent 5/5 

1 night min stay

Add to shortlist

from £73 /night

£509 - £806 / 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

23 Photos

Villa | 1 Bedroom | sleeps 4

Excellent 5/5 

1 night min stay

Add to shortlist

from £49 /night

£340 - £721 / 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

24 Photos

Villa | 6 Bedrooms | sleeps 14

Excellent 5/5 

1 night min stay

Add to shortlist

from £38 /night

£263 - £2120 / 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

22 Photos

Villa | 4 Bedrooms | sleeps 8

6 Nights min stay

Add to shortlist

from £80 /night

£560 - £933 / 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

24 Photos

Farmhouse | 6 Bedrooms | sleeps 12

2 Nights min stay

Add to shortlist

from £206 /night

£1442 - £2404 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • 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

21 Photos

Farmhouse | 3 Bedrooms | sleeps 7

7 Nights min stay

Add to shortlist

from £138 /night

£960 - £1440 / 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

22 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £61 /night

£423 - £603 / 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

22 Photos

Apartment | 1 Bedroom | sleeps 2

2 Nights min stay

Add to shortlist

from £79 /night

£552 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • May take pets – please enquire
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

10 Photos

Apartment | 1 Bedroom | sleeps 4

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £49 /night

£340 - £509 / 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

21 Photos

Farmhouse | 5 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £195 /night

£1360 - £2760 / 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

24 Photos

House | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £63 /night

£440 - £624 / 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

20 Photos

Villa | 5 Bedrooms | sleeps 15

7 Nights min stay

Add to shortlist

from £286 /night

£2000 - £2800 / 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

24 Photos

House | 6 Bedrooms | sleeps 10

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £134 /night

£933 - £1272 / 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

17 Photos

Villa | 2 Bedrooms | sleeps 6

Very Good 4/5 

1 night min stay

Add to shortlist

from £73 /night

£509 - £806 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • 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

6 Photos

Guest house | 6 Bedrooms | sleeps 25

1 night min stay

Add to shortlist

from £78 /night

£543 - £848 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
  • 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

10 Photos

Apartment | 1 Bedroom | sleeps 3

7 Nights min stay

Add to shortlist

from £52 /night

£360 - £633 / 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

9 Photos

Apartment | 2 Bedrooms | sleeps 3

3 Nights min stay

Add to shortlist

from £93 /night

£648 / week

View

Key info:

  • Not suitable for children
  • May take pets – please enquire
Apartment / Condo in Cortona with 2 bedrooms sleeps 3  …see more

8 Photos

Apartment | 1 Bedroom | sleeps 3

1 night min stay

Add to shortlist

from £35 /night

£240 - £320 / week

View

Key info:

  • Suitable for children of all ages
  • Pets welcome
Apartment / Condo in Cortona with 1 bedrooms sleeps 3  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £246 /night

£1716 - £3088 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Cortona with 4 bedrooms sleeps 8  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £216 /night

£1512 - £1833 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 3 bedrooms sleeps 6  …see more

12 Photos

Farmhouse | 5 Bedrooms | sleeps 12

7 Nights min stay

Add to shortlist

from £207 /night

£1448 - £2815 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Cortona with 5 bedrooms sleeps 12  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £48 /night

£334 - £561 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Cortona with 1 bedrooms sleeps 4  …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

12 Photos

Farmhouse | 2 Bedrooms | sleeps 4

3 Nights min stay

Add to shortlist

from £79 /night

£552 - £864 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 2 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 9 Bedrooms | sleeps 18

7 Nights min stay

Add to shortlist

from £338 /night

£2360 - £3432 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Cortona with 9 bedrooms sleeps 18  …see more

11 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £86 /night

£600 - £1008 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 1 bedrooms sleeps 4  …see more

10 Photos

Farmhouse | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £74 /night

£512 - £760 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 1 bedrooms sleeps 2  …see more

10 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £68 /night

£475 - £763 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Cortona with 3 bedrooms sleeps 6  …see more

11 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £48 /night

£334 - £561 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
Villa / Farmhouse / Home in Cortona with 1 bedrooms sleeps 4  …see more

10 Photos

B&B | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £66 /night

£456 / week

View

Key info:

  • Not suitable for children
  • May take pets – please enquire
Bed & Breakfast in Cortona with 1 bedrooms sleeps 2  …see more

12 Photos

Farmhouse | 3 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £86 /night

£600 - £1047 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 3 bedrooms sleeps 6  …see more

12 Photos

Farmhouse | 5 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £155 /night

£1080 - £1800 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Cortona with 5 bedrooms sleeps 14  …see more

10 Photos

Hotel apartment | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £58 /night

£400 - £720 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Residence in Cortona with 2 bedrooms sleeps 6  …see more

12 Photos

Apartment | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £196 /night

£1372 / week

View

Key info:

  • Suitable for children of all ages
  • May take pets – please enquire
Apartment / Condo in Cortona with 4 bedrooms sleeps 8  …see more

10 Photos

Farmhouse | 4 Bedrooms | sleeps 9

7 Nights min stay

Add to shortlist

from £105 /night

£732 - £1764 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Cortona with 4 bedrooms sleeps 9  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 10

3 Nights min stay

Add to shortlist

from £117 /night

£816 - £1361 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Cortona with 4 bedrooms sleeps 10  …see more

12 Photos

Farmhouse | 1 Bedroom | sleeps 4

7 Nights min stay

Add to shortlist

from £57 /night

£396 - £600 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Cortona with 1 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £59 /night

£412 - £620 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 2 bedrooms sleeps 6  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £132 /night

£920 - £2056 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Cortona with 4 bedrooms sleeps 10  …see more

11 Photos

Farmhouse | 1 Bedroom | sleeps 4

3 Nights min stay

Add to shortlist

from £48 /night

£334 - £561 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 1 bedrooms sleeps 4  …see more

12 Photos

Farmhouse | 5 Bedrooms | sleeps 9

3 Nights min stay

Add to shortlist

from £121 /night

£847 - £1608 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Camucia with 5 bedrooms sleeps 9  …see more

12 Photos

Farmhouse | 2 Bedrooms | sleeps 6

3 Nights min stay

Add to shortlist

from £59 /night

£412 - £620 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Cortona with 2 bedrooms sleeps 6  …see more

11 Photos

Farmhouse | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £54 /night

£374 - £560 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Cortona with 1 bedrooms sleeps 2  …see more