List your home
Apply filters
£ to

Holiday homes 29

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

Filters applied: High chair (29)

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
29 Results   |  
24 Photos

Farmhouse / 2 Bedrooms / sleeps 6

Excellent 5/5 

1 night min stay

Add to shortlist

from £45 / night

£309 - £387 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
  • Private garden
Ideal to relax your body and your mind: beatiful landscape and trekking area; ideal place to visit all the central Italy: Arezzo, Cortona, Siena, Perugia, Assisi, La Verna, Camaldoli, Florence and also Rome.  …see more

14 Photos

B&B / 1 Bedroom / sleeps 2

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £42 / night

£294 - £353 / week

View

Key info:

  • Not suitable for children
  • Car essential
  • Some pets are welcome - please contact the owner
tuscany, agriturismo, cortona, Arezzo, Castiglion Fiorentino Within 550 meters is a local bar and grocery store. The medieval town of Castiglion Fiorentino is about 5 km  …see more

18 Photos

Villa / 3 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £85 / night

£589 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Italia, Toscana, casa vacanza, Cortona, Castiglion Fiorentino, Arezzo, etruschi, natura e libertà. A due passi dal lago Trasimeno  …see more

Featured properties

8 Photos

Guest house / 14 Bedrooms / sleeps 39

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £43 / night

£295 - £368 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Gli appartamenti e gli spazi comuni sono stati ristrutturati con classe ed eleganza, offrendo alloggi di lusso e un servizio di alto livello.  …see more

22 Photos

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £153 / night

£1067 - £2339 / 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
Inside the Villa Various paintings of flowers and colours of Tuscany hang on the walls bringing nature indoors. The living room is plain and simple, starting with the stone walls where the fireplace stands. Here you can take a relaxing break while watching satellite T  …see more

18 Photos

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £39 / night

£273 - £295 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Pets welcome
Tuscany Holiday House Castiglion Fiorentino Historical City Center Check-in 3.00 pm - 8.00 pm Check-out before/entro 11.00 am  …see more

24 Photos

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £164 / night

£1143 - £2317 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Magical Villa with private pool on top of Tuscany Hills. One hour drive to Florence, Siena, Perugia. Near to Cortona, Montepulciano and Arezzo.  …see more

22 Photos

Farmhouse / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £83 / night

£581 - £1015 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
The area around Castiglion Fiorentino includes all the characteristics of the typical Tuscan landscapes.  …see more

33 Photos

Farmhouse / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £104 / night

£728 - £1390 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Ancient farmhouse of peasant origins, situated on the top a small hill in the heart of Valdichiana, at approx. 4 km from Castiglion Fiorentino, characteristic village with all kind of shop, restaurants and facilities.  …see more

37 Photos

Farmhouse / 4 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £119 / night

£831 - £1508 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Old farmhouse of peasant origins, where on the ground floor you can still appreciate the old stables. Located 1,5 km away from the town of Castiglion Fiorentino which can also be reached on foot.  …see more

24 Photos

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

Add to shortlist

from £368 / night

£2574 - £5148 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury villa with swimming pool, indoor pool and sauna near Cortona – sleeps 18+6 SPECIAL 10% SPRING DISCOUNT on full occupancy valid in April and May Possibility to add 6 extra beds  …see more

11 Photos

Apartment / 2 Bedrooms / sleeps 4

2 Nights min stay

Add to shortlist

from £37 / night

£258 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Tuscany Holiday House  …see more

15 Photos

Cottage / 4 Bedrooms / sleeps 15

2 Nights min stay

Add to shortlist

from £116 / night

£809 - £1618 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
Spinabbio è il luogo ideale per passare al meglio le vostre vacanze tra relax e cultura.Potrete visitare la vicinissima Cortona,Arezzo,Siena e Perugia.  …see more

18 Photos

Villa / 5 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £95 / night

£662 - £1412 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
La casa è dotata di tutti i confort per una piacevole vacanza in tranquillità e relax. Piscina grande per rinfrescarsi nelle giornate estive e grande vasca idromassaggio riscaldata situata all'esterno con vista sulle colline di Castigion Fiorentino. Nel Giardino, dotat  …see more

5 Photos

Condo / 2 Bedrooms / sleeps 5

1 night min stay

Add to shortlist

from £37 / night

£258 - £478 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
Ferienwohnung, Campingplatz, Naturpool, Reiten, Biogemüse, Natur, Entspannung, Hunde erlaubt, Pferde willkommen Babybett auf Anfrage, Handtücher (für's Bad) und Bettwäsche vorhanden  …see more

23 Photos

Apartment / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £63 / night

£438 - £489 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
AGRITURISMO, BED AND BREAKFAST, CASTIGLION FIORENTINO, PISCINA, BARBECUE, MOUNTAIN BIKE, OLIO EXTRA VERGINE DI OLIVA, ANIMALI AMMESSI, SPAZIO GIOCO BIMBI, COLAZIONE.  …see more

11 Photos

Townhouse / 2 Bedrooms / sleeps 5

2 Nights min stay

Add to shortlist

from £48 / night

£331 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Come si arriva alla Fenice: dall'autostrada A1, uscita Monte San Savino si raggiunge Castiglion F.no dove si arriva alla ss n°71, qui si prosegue a destra in direzione Perugia e, al terzo semaforo, si svolta a sinistra seguendo le indicazioni per S. Cristina. Dopo circ  …see more

4 Photos

Apartment / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £11 / night

£74 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
IMMERSO NELLA INCONTAMINATA E TRANQUILLA VALLE DI CHIO AFFITTO APPARTAMENTO 180 MQ CON GRANDE TERRAZZO SONO FACILMENTE RAGGIUNGIBILI IN AUTO E IN TRENO CITTà 'ARTE COME SIENA FIRENZE ROMA PERUGIA Città DI CASTELLO E PAESINI LIMITROFI CON CARATTERISTICHE FESTE PAESANE.  …see more

8 Photos

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £141 / night

£981 - £2745 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Situated on the border between Tuscany and Umbria, this lovely country villa has been recently built in perfect harmony with the surrounding territory.  …see more

23 Photos

Farmhouse / 4 Bedrooms / sleeps 10

3 Nights min stay

Add to shortlist

from £142 / night

£993 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
An ideal choice for those who love nature and art, in an authentic and elegant environment. Highly recommended for families with children. The feature of the farm is quiet and respect for the environment At the dining room of the homeowner you can book dinners made with local produce.  …see more

24 Photos

Villa / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £104 / night

£728 - £1096 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
ENCHAINTING VILLA with private POOL on top of TUSCAN HILLS. 10 minutes drive to the town of Castiglion Fiorentino. 25 to CORTONA. One hour to FIRENZE, PERUGIA and SIENA. 30 minutes to the TRASIMENO LAKE.  …see more

24 Photos

Villa / 4 Bedrooms / sleeps 11

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £158 / night

£1103 - £2648 / week

View

Key info:

  • Nearest beach 128 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Opened in 2010 .Beautiful villa in panoramic position with private pool in the countryside 8/11persons.Peaceful e charming location, ideal for families or groups. 4 bedroom / 6 bathroom. Only 10km from Cortona , 10 min from the village of Castiglion Fiorentino.  …see more

24 Photos

Cottage / 2 Bedrooms / sleeps 4

Excellent 5/5 

Short stays welcome

Add to shortlist

from £68 / night

£471 - £692 / week

View

Key info:

  • Nearest beach 27 km
  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
There is also a separate studio with additional bed and bathroom if you need more space . Great value family holiday homes in Tuscany, Large pool and amazing views. Perfectly to tour Tuscany and Umbria including the towns of Cortona, Pienza, Arezzo, Assisi, Siena etc  …see more

24 Photos

Cottage / 2 Bedrooms / sleeps 4

Excellent 5/5 

Short stays welcome

Add to shortlist

from £77 / night

£534 - £655 / 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
*** Extra guests? There is also a separate studio available which has additional bed and bathroom should you require additional space. The property is great for half term school holidays as well as the longer summer family holidays in Tuscany.  …see more

15 Photos

Apartment / 2 Bedrooms / sleeps 5

Excellent 5/5 

Short stays welcome

Add to shortlist

from £69 / night

£478 - £692 / week

View

Key info:

  • Nearest beach 25 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Quiet location in old Tuscan villa. Large pool, spacious apartment with a lovely walk to shop and bar, Quiet peaceful location. Clean and bright family holiday rental. Lots of help if you need it with travel plans including visits to vineyards, cooking classes and more The old stone pizza oven is available for pizza and other barbecue specialties.  …see more

24 Photos

Cottage / 3 Bedrooms / sleeps 5

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £77 / night

£534 - £787 / week

View

Key info:

  • Nearest beach 26 km
  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Late availability, Good value Family Holiday Tuscany, Perfect for half term holidays as well as extended summer vacations in Tuscany. One of three, lovely detached cottages lovingly restored with large pool and gardens. Large pizza oven, private terraces and pergolas.  …see more

24 Photos

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

Add to shortlist

from £368 / night

£2574 - £5148 / week

View

Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Magnifica is an old country residence, skilfully restored and transformed into an exclusive private retreat. A 4 acres park, with Italian style garden and olive trees, surround the property.  …see more

17 Photos

Villa / 4 Bedrooms / sleeps 12

4 Nights min stay

Add to shortlist

from £215 / night

£1500 - £3100 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Villa la Rustica is a private villa situated 550 meters above sea level and nestled in an isolated Tuscan hillside surrounded by olive groves and oak trees. It is located 8 km from the town of Castiglion Fiorentino and a step away from Cortona and Umbria.  …see more

26 Photos

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £165 / night

£1155 - £2199 / week

View

Key info:

  • Nearest beach 23 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
In the shadows of Castiglion Fiorentino, This impeccable and charming villa is perfect for touring Cortona, Pienza, Montepulciano and many of the Tuscan hill towns. It is perfect for family reunions, a vacation for friends - but always, something special to enjoy  …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