List your home
Apply filters
£ to

21 Holiday homes in Castiglion Fiorentino

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
2,420 properties
Florence
947 properties
Trapani
498 properties
Venice, Veneto
481 properties
Amalfi Coast
457 properties
Cortona
428 properties
Lucca
428 properties
Palermo
383 properties
Sorrento, Campania
350 properties
Cefalu
310 properties
San Gimignano
296 properties
Greve in Chianti
267 properties
Taormina
260 properties
Syracuse
250 properties

Filters applied: Smokers (21)

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
21 Results  |  
18 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £315 /night

£2205 - £2714 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Magnificent villa with swimming pool between Arezzo and Cortona  …see more

13 Photos

Apartment | 2 Bedrooms | sleeps 4

Short stays welcome

Add to shortlist

from £96 /night

£670 - £933 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
The farm is nestled in the enchanting Tuscan hillside of the Val di Chio located between Arezzo and Cortona  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £176 /night

£1230 - £2697 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • 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

Featured properties

21 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £176 /night

£1230 - £2332 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Villa with swimming pool near Cortona, with stunning view over the olive groves and the town of Castiglion Fiorentino  …see more

24 Photos

Cottage | 2 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

Add to shortlist

from £83 /night

£580 - £636 / week

View

Key info:

  • Nearest beach 27 km
  • Swimming pool
  • Suitable for over 5s only
  • Car essential
  • May take pets – please enquire
  • 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 £80 /night

£556 - £628 / week

View

Key info:

  • Nearest beach 25 km
  • Swimming pool
  • Suitable for over 5s only
  • Car essential
  • May take pets – please enquire
  • Private garden
Extra guests? There is also a separate studio available which has additional bed and bathroom should you require additional space. The proeprty is great for half term school holidays as well as the longer summer family holidays in Tuscany.  …see more

12 Photos

House | 6 Bedrooms | sleeps 13

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £357 /night

£2499 - £3239 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Il Ceriolo is a restored 18th century Tuscan farm house set on about five acres of land. The house includes six bedrooms and five baths, with a sleeping capacity of 13. A lovely pool is included. The pool is quite large and very private. An outdoor barbeque is available, along with alfresco dining.  …see more

9 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £201 /night

£1404 - £2592 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Casale Fiorentinaandnbsp;is a beautiful stone farmhouse located inandnbsp;Castiglion Florentinoandnbsp;amidst the Tuscan country side with its olive groves and rich vineyards.andnbsp; Theandnbsp;kitchenandnbsp;opens onto the outside dining area, a covered porch  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 9

7 Nights min stay

Add to shortlist

from £164 /night

£1144 - £2632 / week

View

Key info:

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

12 Photos

Farmhouse | 4 Bedrooms | sleeps 8

3 Nights min stay

Add to shortlist

from £212 /night

£1480 - £2544 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
  • Private garden
Villa / Farmhouse / Home in Castiglion Fiorentino with 4 bedrooms sleeps 8  …see more

18 Photos

Villa | 9 Bedrooms | sleeps 18

3 Nights min stay

Add to shortlist

from £400 /night

£2800 - £7280 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Welcome to the Tuscany wedding villa Michele in Arezzo, Italy that has the capacity ofandnbsp;18 peopleandnbsp;with babysitter and andnbsp;indoor pool facilities. andnbsp;The Tuscan Villa Michele is an old country residence specially remodeled into an exclusive  …see more

12 Photos

Farmhouse | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £195 /night

£1360 - £1960 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • May take pets – please enquire
  • Private garden
Villa / Farmhouse / Home in Castiglion Fiorentino with 4 bedrooms sleeps 8  …see more

23 Photos

Apartment | 1 Bedroom | sleeps 2

5 Nights min stay

Add to shortlist

from £81 /night

£564 / week

View

Key info:

  • Swimming pool
  • Suitable 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

8 Photos

Guest house | 14 Bedrooms | sleeps 39

2 Nights min stay

Add to shortlist

from £61 /night

£424 / week

View

Key info:

  • Swimming pool
  • Suitable 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

24 Photos

House | 1 Bedroom | sleeps 2

3 Nights min stay

Add to shortlist

from £70 /night

£488 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • Pets welcome
Agriturismo in posizione collinare dominante la Valle di Chio. A pochi kilometri da importanti città d'arte come Firenze, Siena, Perugia. Piscina 9x15. Maneggio 1km campi da tennis 1km  …see more

10 Photos

Townhouse | 2 Bedrooms | sleeps 5

2 Nights min stay

Add to shortlist

from £55 /night

£382 - £636 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • May take pets – please enquire
  • 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

16 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

Add to shortlist

from £31 /night

£212 / week

View

Key info:

  • Suitable for children of all ages
  • Pets welcome
Bicamere in palazzo antico nel centro storico di caratteristico borgo toscano. Apartment in the historic centre of Castiglion Fiorentino, a typical Tuscan hill-top town, in a region's uniquely rich for cultural and artistic heritage (Tuscany and nearby Umbria)  …see more

12 Photos

Villa | 3 Bedrooms | sleeps 8

1 night min stay

Add to shortlist

from £85 /night

£594 / week

View

Key info:

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

17 Photos

Villa | 4 Bedrooms | sleeps 12

Min stay varies

Add to shortlist

from £213 /night

£1490 - £3430 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • 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

19 Photos

Villa | 4 Bedrooms | sleeps 10

Min stay varies

Add to shortlist

from £180 /night

£1260 - £2980 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Villa Chio is nestled in the Tuscan hillside covered by an olive grove at 350 meters above sea level in a panoramic position showcasing the town of Castiglion Fiorentino.  …see more

20 Photos

Apartment | 2 Bedrooms | sleeps 5

Min stay varies

Add to shortlist

from £63 /night

£440 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • Pets welcome
This 2 bedroom, 2.0 bath vacation apartment in Castiglion Fiorentino, Tuscany offers uncompromising style and comfort, and sleeps up to 5 comfortably. It is equipped with everything you need to enjoy your stay. This Apartment is a great vacation rental  …see more