List your home
Apply filters
£ to

Holiday homes 589

Reset search

Show results on map

Filter your search

Price per night

Price per night

£ to per night

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Province of Arezzo Clear
  • Cortona Clear

Location

  • All locations
  • Bagnolo (9)
  • Cantalena (1)
  • Capezzine (3)
  • Cegliolo (7)
  • Centoia (6)
  • Farinaio (5)
  • Fratta Sant'Agata (1)
  • Fratta Santa Caterina (11)
  • Fratticciola (18)
  • Localita Mucchia (5)
  • Mercatale (3)
  • Mercatale di Cortona (18)
  • Montalla (9)
  • Montanare (10)
  • Montecchio (2)
  • Montecchio, San Lorenzo (4)
  • Poggioni (4)
  • Ruffignano (1)
  • Teverina (3)

more +

less -

Also consider

Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Mercatale di Cortona
18 properties
Fratticciola
18 properties
Fratta Santa Caterina
11 properties
Montanare
10 properties
Montalla
10 properties
Bagnolo
9 properties
Cegliolo
7 properties
Centoia
6 properties
Localita Mucchia
5 properties
Farinaio
5 properties
Payment Protection
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
589 Results   |  

Very Good 4/5 

28 Photos

Province of Arezzo / Cortona

Villa / 3 Bedrooms / sleeps 7

Very Good 4/5 

7 Nights min stay

Add to shortlist

from £130 / night

£909 - £1977 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • Pets welcome
RECEPTIVE STRUCTURE. “Le Volpaie” is a country house in the middle of the splendid Valdichiana landscape, 10 minutes from Cortona, a characteristic historic Tuscan centre capable of hosting a great number of foreigners during the summer time. Our holiday house is se  …see more


26 Sep 2013

4/5

"This is the Italy you've dreamed about"

This lovely farmhouse is about 200 years old and renovated to show off its charm yet has all amenities. It really feels as though you are staying at a friend's beautiful home with books and photos thr… More

See all reviews Continue

Very Good 4.5/5 

40 Photos

Province of Arezzo / Cortona

Villa / 5 Bedrooms / sleeps 12

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £220 / night

£1538 - £2602 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • Pets welcome
PRIVATE STRUCTURE. A stone parlour, where art and nature unite to form a perfect partnership: Cortona is a magical place with a timeless charm that envelops the visitor with its vibrant atmosphere, suspended between the history and legend of its origins, surprising him  …see more


6 Jul 2014

5/5

"Great place for relaxation"

This is a great place to relax but still see a lot in the little hill towns in the area. The accommodations were complete with a great kitchen and well furnished bedrooms. The caretaker stopped by… More


25 Jun 2014

5/5

"A truly relaxing place to stay"

We stayed here the second week of June. There were four couples, no children, and the villa met all our expectations. Each room was lovely, nicely appointed, and everyone had their own private bath. T… More


22 Jun 2014

4/5

"Lovely place to chill out!"

A lovely 600 year old farmhouse that has been lovingly restored and beautifully decorated in a cozy style. We were 4 couples and the house was plenty big with private space and bath for each couple. … More

See all reviews Continue

24 Photos

Province of Arezzo / Cortona

House / 4 Bedrooms / sleeps 8

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
The house has been designed with two bathrooms, country kitchen and living room on each of two floors and provides ample space for eight people, while also offering privacy between floors. Ideal for up to four couples, the house lends itself to a group of friends or int  …see more

Featured properties

32 Photos

Province of Arezzo / Cortona

House / 9 Bedrooms / sleeps 25

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Close to the main house lies a stone independent farmhouse ("Casetto"), recently renovated and equipped with all comforts. It is made up of two independent apartments, each for 4 people. A lovely stone path leads to the loggia, fully equipped for open-air meals. On the  …see more

12 Photos

Province of Arezzo / Cortona

Farmhouse / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £112 / night

£780 - £1366 / week

View

Key info:

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

10 Photos

Province of Arezzo / Cortona

Farmhouse / 2 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £48 / night

£332 - £581 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa / Farmhouse / Home in Cortona with 2 bedrooms sleeps 6  …see more

100 Photos

Province of Arezzo / Cortona

Apartment / 3 Bedrooms / sleeps 7

2 Nights min stay

Add to shortlist

from £52 / night

£363 - £472 / week

View

Key info:

  • Nearest beach 130 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
These apartments near Cortona offer living area with sofa bed and kitchen corner, double and twin bedrooms with bathroom with shower. They host up to 6 or 7 people.  …see more

20 Photos

Cortona / Bagnolo

Villa / 5 Bedrooms / sleeps 11

3 Nights min stay

Add to shortlist

from £126 / night

£876 - £1752 / week

View

Key info:

  • Nearest beach 150 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Farmhouse near Cortona, in the Chiana Valley with wonderful panoramic view. Ideal solution for relaxing holidays in the Tuscan countryside. Swimming pool, barbecue, Internet connection, table-tennis table, mountain bikes. Tennis club and riding stable nearby.  …see more

12 Photos

Cortona / Montalla

Farmhouse / 4 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £127 / night

£885 - £1549 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa in Il Castagno with 4 bedrooms sleeps 8  …see more

20 Photos

Province of Arezzo / Cortona

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £120 / night

£834 - £1812 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Berta is a spacious three-story villa surrounded by the greenery. It sleeps 12 people. From Villa Berta you will have a pleasant view of the Tuscan countryside. Villa Berta is 170 square meters (1830 square feet)  …see more

17 Photos

Province of Arezzo / Cortona

Apartment / 1 Bedroom / sleeps 4

7 Nights min stay

Add to shortlist

from £55 / night

£380 - £450 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Casa Severina is a characteristic apartment. It sleeps four people. From Casa Severina you will have a partial view of Piazza della Repubblica (Republic Square). Casa Severina is 65 square meters (700 square feet)  …see more

100 Photos

Province of Arezzo / Cortona

Apartment / 2 Bedrooms / sleeps 6

2 Nights min stay

Add to shortlist

from £46 / night

£316 - £399 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Reggia Etruria is a wonderful complex of 4 apartments in Tuscany, all fitted with modern amenities and extremely comfortable, surrounded by a splendid panoramic garden with swimming, pool, and located nearby Arezzo, Pienza, Siena, and Cortona.  …see more

32 Photos

Province of Arezzo / Cortona

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £239 / night

£1667 - £2682 / week

View

Key info:

  • Nearest beach 160 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This lovely villa near Cortona can accommodate up to 10 people. It has a swimming pool and 3 bedrooms with en-suite bathrooms.  …see more

24 Photos

Province of Arezzo / Cortona

House / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £59 / night

£407 - £776 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This pretty, rustic, air-conditioned holiday cottage is located in a small hamlet consisting of 4 stone-built houses on a hill overlooking the valley. This property is one of 3 holiday rentals and the fourth house belongs to the owner. With traditional furnishings an...  …see more

12 Photos

Province of Arezzo / Cortona

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £300 / night

£2097 - £3008 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa in Cortona with 6 bedrooms sleeps 12  …see more

24 Photos

Province of Arezzo / Cortona

Farmhouse / 4 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £172 / night

£1202 - £2138 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa in Cortona with 4 bedrooms sleeps 8  …see more

25 Photos

Province of Arezzo / Cortona

House / 3 Bedrooms / sleeps 6

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
The Villa consists of 2 floors: on the ground floor a lovely large living/dining room, the small but fully equipped kitchen with wood-burning oven, although small it has everything you need to prepare some wonderful Tuscan meals; There is a dining room and hall. These a  …see more

23 Photos

Province of Arezzo / Cortona

House / 6 Bedrooms / sleeps 6

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
The villa's furnishing combines antiques with comfort and contributes to creating a lovely atmosphere. Main Villa Ground floor: The entrance opens to a reading room and onto a combined living and dining room. This room has a couch, chairs, fireplace, and a table with c  …see more

32 Photos

Province of Arezzo / Cortona

House / 3 Bedrooms / sleeps 3

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
The property has been lovingly restored using only natural, chemical-free products to preserve the serenity this special place. There is a cork roof, the floors are made of warm Tuscan terracotta and the walls are painted with water colours. Ground floor: There is a si  …see more

17 Photos

Province of Arezzo / Cortona

House / 3 Bedrooms / sleeps 6

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
Tucked in a huge olive grove, chestnut and holm oak wood, the villa offers its guests a breathtaking view over the Valdichiana and the Cortona hills and is the ideal location for those who wish to enjoy total privacy. The ground floor is accessed through the cosy sitti  …see more

14 Photos

Province of Arezzo / Cortona

House / sleeps 6

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
The house is made up of two floors and can sleep up to 6 people. The ground floor has a spacious sitting room with an open fireplace and a comfortable sofa. The fully equipped kitchen hosts a large dining area. Bathroom and laundry room outdoor. A wooden staircase lea  …see more

39 Photos

Province of Arezzo / Cortona

House / sleeps 8

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
Casina Giallo is a charming old house, that has recently been restored, at the top of the Cortona hill commanding a wonderful view. There one can enjoy the changes of season as well as the country life and the rich vegetation of this corner of Tuscany. Casina Giallo is  …see more

21 Photos

Province of Arezzo / Cortona

House / sleeps 1

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
Tucked in the hills of Cortona, under the ancient Etruscan walls that encircle this beautiful town, lies Casina Rianna, which is surrounded by olive groves, out of which the owners make an excellent extra virgin olive oil which you may taste. Casina Rianna is an old st  …see more

33 Photos

Province of Arezzo / Cortona

House / 6 Bedrooms / sleeps 6

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
The Villa has been recently remodelled and equipped with air-conditioning and heating. The interiors are decorated in a Provençal style with soft colors and decorated wood furnishings that will make your holiday comfort unforgettable. The villa is a perfect example  …see more

18 Photos

Province of Arezzo / Cortona

House / sleeps 5

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
Recently restored old stone Villa of Casona lies up on the hill and is part of a beautiful Renaissance Villa. Located near Cortona, the villa is surrounded by old pine, cypress, lime and oak trees which provide perfect areas for relaxing and reading. The beautiful swimm  …see more

24 Photos

Province of Arezzo / Cortona

House / 8 Bedrooms / sleeps 15

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Very close to Cortona ( look up and you will see one of its iconic church domes from nearly every window). You enter the estate by a lovely pebbled drive, and before you are the two buildings that make up this large villa rental in Tuscany. It can be rented for up to 17  …see more

23 Photos

Province of Arezzo / Cortona

House / sleeps 8

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
On the border between Umbria and Tuscany, this lovely restored country house is set on the hillside with lovely views from all rooms. Very private setting. The farmhouse is about 300 square metres (3000 sq ft), surrounded by 6,5 hectares land, equipped with modern comfo  …see more

26 Photos

Province of Arezzo / Cortona

House / sleeps 5

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
The villa is built on two floors. Ground floor: comfortably furnished sitting room, fully equipped kitchen, dining room, a double room and a bathroom. A wooden staircase takes you up to the first floor where there is a little kitchen, a double room, a twin bed room and  …see more

8 Photos

Province of Arezzo / Cortona

House / 3 Bedrooms / sleeps 3

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
Vittorio Sopra is an apartment of 270 sqm in a charming farmhouse ideal for 8 people.The house is furnished according the traditional Tuscan country style: Terracotta tiled floors, exposed wooden beams and hand crafted wrought iron beds. First floor: large kitchen with  …see more

17 Photos

Province of Arezzo / Cortona

House / 10 Bedrooms / sleeps 20

7 Nights min stay

Add to shortlist

from £741 / night

£5183 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
The villa is built on three floors. The ground floor hosts two sitting rooms, a dining room with a large wooden table which seats 20, a fully equipped kitchen with dishwasher, one half-bathroom, a cellar and a laundry room. The first floor consists of two spacious doubl  …see more

33 Photos

Province of Arezzo / Cortona

House / sleeps 15

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
The accommodation consists of two terracotta-brick farmhouses, not interconnecting with each other, giving the possibility for a large group to holiday together yet retain their own privacy. The new English owner has recently bought and completely restored the origina  …see more

24 Photos

Province of Arezzo / Cortona

House / 6 Bedrooms / sleeps 11

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
To provide guests with maximum flexibility in their accommodations, the house has been divided into two independent floors, each with country kitchen opening on to terraces for lounging and outdoor dining. On the upper floor, the house has three double bedrooms and two  …see more

10 Photos

Province of Arezzo / Cortona

House / sleeps 2

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
Casa Carina, a reconstructed stone barn, which was once a key element in an extended agricultural estate. Recently restored, the house has a dramatic, luminous two-story living room with picture window imbedded in a lovely stone wall, which rises like a natural sculptur  …see more

22 Photos

Province of Arezzo / Cortona

House / sleeps 14

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Not suitable for children
  • No pets allowed
Set in a large garden, each of the houses has a well-equipped patio for dining outdoors, with stunning views of the surrounding countryside. Large picture windows in the living area of both houses allow one to enjoy the panorama of the rolling Umbrian hills The interio  …see more

23 Photos

Cortona / Fratticciola

Farmhouse / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £69 / night

£479 - £826 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Cà Di Masino with 2 bedrooms sleeps 4  …see more

12 Photos

Cortona / Fratticciola

Farmhouse / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £48 / night

£332 - £479 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Cà Di Masino with 1 bedrooms sleeps 2  …see more

22 Photos

Cortona / Fratticciola

Farmhouse / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £69 / night

£479 - £826 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Cà Di Masino with 2 bedrooms sleeps 4  …see more

16 Photos

Cortona / Fratticciola

Farmhouse / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £69 / night

£479 - £826 / week

View

Key info:

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

21 Photos

Cortona / Fratticciola

Farmhouse / 2 Bedrooms / sleeps 5

3 Nights min stay

Add to shortlist

from £69 / night

£479 - £826 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Cà Di Masino with 2 bedrooms sleeps 5  …see more

17 Photos

Cortona / Fratticciola

Farmhouse / 1 Bedroom / sleeps 4

3 Nights min stay

Add to shortlist

from £58 / night

£406 - £627 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Cà Di Masino with 1 bedrooms sleeps 4  …see more

18 Photos

Cortona / Fratticciola

Farmhouse / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £48 / night

£332 - £479 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Cà Di Masino with 1 bedrooms sleeps 2  …see more

18 Photos

Cortona / Fratticciola

Farmhouse / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £58 / night

£406 - £627 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Cà Di Masino with 2 bedrooms sleeps 4  …see more

21 Photos

Cortona / Fratticciola

Farmhouse / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £48 / night

£332 - £479 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Cà Di Masino with 1 bedrooms sleeps 2  …see more

7 Photos

Province of Arezzo / Cortona

Apartment / 1 Bedroom / sleeps 4

3 Nights min stay

Add to shortlist

from £44 / night

£308 - £438 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Apartment / Condo in Cortona with 1 bedrooms sleeps 4  …see more

8 Photos

Province of Arezzo / Cortona

Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £69 / night

£482 - £685 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Apartment / Condo in Cortona with 2 bedrooms sleeps 4  …see more

9 Photos

Province of Arezzo / Cortona

Apartment / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £55 / night

£383 - £499 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Apartment / Condo in Cortona with 1 bedrooms sleeps 2  …see more

24 Photos

Province of Arezzo / Cortona

Farmhouse / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £199 / night

£1393 - £1689 / week

View

Key info:

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

10 Photos

Province of Arezzo / Cortona

Farmhouse / 1 Bedroom / sleeps 2

7 Nights min stay

Add to shortlist

from £68 / night

£471 - £700 / week

View

Key info:

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

9 Photos

Province of Arezzo / Cortona

Apartment / 1 Bedroom / sleeps 3

3 Nights min stay

Add to shortlist

from £55 / night

£383 - £499 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Apartment / Condo in Cortona with 1 bedrooms sleeps 3  …see more

22 Photos

Province of Arezzo / Cortona

Farmhouse / 1 Bedroom / sleeps 2

7 Nights min stay

Add to shortlist

from £68 / night

£471 - £700 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa in Cortona with 1 bedrooms sleeps 2  …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