List your home
Apply filters
£ to

Holiday homes 40

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
  • Castiglion Fiorentino Clear

Location

  • All locations
  • Montecchio Vesponi (3)
  • Orzale (3)
  • Santa Maria Alla Rassinata (1)

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

Filters applied: Tennis in town (40)

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
40 Results   |  

Excellent 5/5 

18 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

1 night min stay

Add to shortlist

from £183 / night

£1277 - £1915 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Magnificent villa with swimming pool between Arezzo and Cortona  …see more

21 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £163 / night

£1135 - £2057 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Villa with swimming pool near Cortona, with stunning view over the olive groves and the town of Castiglion Fiorentino  …see more

20 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 2 Bedrooms / sleeps 3

3 Nights min stay

Add to shortlist

from £46 / night

£320 - £426 / week

View

Key info:

  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
The picturesque Via San Lazzo, named after the characteristic small Romanesque church, winds along the massive Medieval walls surrounding the Etruscan town of Castiglion Fiorentino, once entered Porta Romana.  …see more

Featured properties

24 Photos

Castiglion Fiorentino / Santa Maria Alla Rassinata

Villa / 4 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £152 / night

£1064 - £1532 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
In the Cortona countryside, 2 km from Castiglion Fiorentino. private garden wiht large pool.  …see more

Excellent 5/5 

24 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £158 / night

£1103 - £2235 / 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

24 Photos

Castiglion Fiorentino / Orzale

Villa / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £86 / night

£596 - £1057 / 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

Excellent 5/5 

22 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £147 / night

£1029 - £2256 / 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

Excellent 5/5 

14 Photos

Province of Arezzo / Castiglion Fiorentino

B&B / 1 Bedroom / sleeps 2

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £41 / night

£283 - £341 / 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

Excellent 5/5 

8 Photos

Province of Arezzo / Castiglion Fiorentino

Guest house / 14 Bedrooms / sleeps 39

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £41 / night

£284 - £355 / 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

Excellent 5/5 

18 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 3 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £82 / night

£568 / 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

Excellent 5/5 

8 Photos

Province of Arezzo / Castiglion Fiorentino

House / 2 Bedrooms / sleeps 5

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £46 / night

£320 - £547 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Struttura piccola ma confortevole, capace di farvi passare le vostre vacanze in un luogo fantastico immerso nel verde, ma allo stesso tempo vicino alle principali città del centro della toscana. www.lamontanina.altervista.org  …see more

Excellent 5/5 

23 Photos

Province of Arezzo / Castiglion Fiorentino

Townhouse / 2 Bedrooms / sleeps 5

Excellent 5/5 

1 night min stay

Add to shortlist

from £48 / night

£334 - £461 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Pets welcome
La casa è a metà strada tra Cortona e Arezzo che sono raggiungibili anche con i servizi di trasporto pubblico e rappresenta un ottimo punto di partenza per gite in Val d'Orcia, al Lago Trasimeno o per escursioni nelle valli e colline circostanti. Attrezzato centro spo  …see more

19 Photos

Castiglion Fiorentino / Montecchio Vesponi

B&B / 6 Bedrooms / sleeps 12

1 night min stay

Add to shortlist

from £61 / night

£426 - £497 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Offriamo una vacanza all'insegna del benessere e del relax. Siamo vicino ai maggiori luoghi di interesse turistico della Toscana e dell'Umbria. Cortona, Montepulciano, Arezzo, Siena, Firenze, Pienza, il Lago Trasimeno, si raggiungono in meno di un'ora di macchina.  …see more

18 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 5 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £92 / night

£639 - £1362 / 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, dot  …see more

Excellent 5/5 

18 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £38 / night

£263 - £284 / 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

18 Photos

Province of Arezzo / Castiglion Fiorentino

B&B / 3 Bedrooms / sleeps 2

1 night min stay

Add to shortlist

from £51 / night

£355 - £412 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Relax, eco sostenibilità, campagna, piscina e buona tavola, sono le caratteristiche che ci distinguono e che vi faranno apprezzare maggiormente le bellezze di questa parte della Toscana.  …see more

21 Photos

Castiglion Fiorentino / Montecchio Vesponi

House / 4 Bedrooms / sleeps 11

6 Nights min stay

Add to shortlist

from £82 / night

£568 - £1454 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Strategic location to visit TUSCANY. Full packages available with tours (wine, food, historical, religious and many others).  …see more

11 Photos

Castiglion Fiorentino / Orzale

Townhouse / 2 Bedrooms / sleeps 5

Min stay varies

Add to shortlist

from £46 / night

£320 - £532 / 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 cir  …see more

11 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 2 Bedrooms / sleeps 6

2 Nights min stay

Add to shortlist

from £36 / night

£249 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
Tuscany Holiday House  …see more

24 Photos

Province of Arezzo / Castiglion Fiorentino

House / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £53 / night

£366 - £408 / week

View

Key info:

  • Swimming pool
  • Great 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

14 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £122 / night

£851 - £1752 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Holiday property located in Tuscany in Castiglion Fiorentino. Close location to many touristic attractions like Cortona, Arezzo, Siena, Montepulciano, Montalcino, Chianti, Florence and many more makes it a fantastic place for family holidays.  …see more

7 Photos

Province of Arezzo / Castiglion Fiorentino

Townhouse / 2 Bedrooms / sleeps 5

2 Nights min stay

Add to shortlist

from £31 / night

£213 - £320 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
Grazioso e comodo appartamento con giardino e garage, a Castiglion Fiorentino (Toscana). 2 camere da letto, max 5 ospiti. Per un tranquillo periodo di vacanza. A 10 Km da Cortona, 15 Km da Arezzo, 50 Km da Perugia, 60 Km da Siena, 90 Km da Firenze.  …see more

24 Photos

Castiglion Fiorentino / Montecchio Vesponi

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

Add to shortlist

from £355 / night

£2483 - £4965 / 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

24 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

Add to shortlist

from £355 / night

£2483 - £4965 / 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

Excellent 5/5 

20 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 9

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £117 / night

£813 - £2334 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
The villa, of recent reconstruction, is positioned on the hills next to the characteristic town of Castiglion Fiorentino, in the middle of the Chiana valley and Chio valley amidst nature and art.  …see more

Excellent 5/5 

23 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £193 / night

£1348 - £2518 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Good value Tuscan Home for families or friends, Private pool, beautiful views, lots of space both inside and out. Additional facilities can be provided - A chef to prepare a lovely lunch or dinner for that special occasion, a concierge serve with local insight,  …see more

Very Good 4.5/5 

13 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 5 Bedrooms / sleeps 10

Very Good 4.5/5 

7 Nights min stay

Add to shortlist

from £145 / night

£1013 - £1717 / week

View

Key info:

  • Nearest beach 27 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Just a short distance from the medieval town of Castiglion Fiorentino is "Casa Usignoli". This very old manor house dates back to 1759. It has been fully renovated to provide a stylish family home with 5 large bedrooms and two bathrooms.  …see more

18 Photos

Province of Arezzo / Castiglion Fiorentino

House / 5 Bedrooms / sleeps 11

7 Nights min stay

Add to shortlist

from £231 / night

£1614 - £2093 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Magnificent villa in a beautiful hillside position with breathtaking views, close to the medieval walled village of Castiglion Fiorentino.  …see more

17 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £46 / night

£320 - £561 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
it is the ideal place if you are looking to relax and beautiful view  …see more

Excellent 5/5 

24 Photos

Province of Arezzo / Castiglion Fiorentino

Cottage / 2 Bedrooms / sleeps 4

Excellent 5/5 

Short stays welcome

Add to shortlist

from £80 / night

£557 - £632 / week

View

Late Deal: save up to €202 (approx. £143)

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

Very Good 4.5/5 

16 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 2 Bedrooms / sleeps 4

Very Good 4.5/5 

7 Nights min stay

Add to shortlist

from £70 / night

£486 - £699 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
2 bedroom family apartment in Tuscany, with pool. Easy access to towns and the closest shop/bar and restaurant are within an easy stroll. A perfect family holiday with lots to do here and in our surrounding hill towns. Wine tours, Cooking classes and much more.  …see more

Excellent 5/5 

24 Photos

Province of Arezzo / Castiglion Fiorentino

Cottage / 2 Bedrooms / sleeps 4

Excellent 5/5 

Short stays welcome

Add to shortlist

from £74 / night

£515 - £667 / 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

Excellent 5/5 

15 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 2 Bedrooms / sleeps 5

Excellent 5/5 

Short stays welcome

Add to shortlist

from £66 / night

£461 - £667 / 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  …see more

Excellent 5/5 

23 Photos

Castiglion Fiorentino / Orzale

Condo / 1 Bedroom / sleeps 2

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £62 / night

£430 - £523 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
This romantic garden cottage, sits in the sleepy hamlet of Orzale and provides the perfect place to unwind and enjoy Tuscany. Simple, but charming accommodation - and a private pool. Capuchi cottage is immersed in the beautiful Tuscan country side. Private and cosy, p  …see more

Very Good 4.5/5 

23 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 8

Very Good 4.5/5 

7 Nights min stay

Add to shortlist

from £122 / night

£852 - £1348 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
Castello Margarita is the ideal spot for those seeking relaxation and the convenience to explore Tuscany. Ideal for 4 - 16 guests It provides a compelling combination of a great location and charming farmhouse style.  …see more

Very Good 4.5/5 

24 Photos

Province of Arezzo / Castiglion Fiorentino

Cottage / 3 Bedrooms / sleeps 5

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £74 / night

£515 - £759 / 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

19 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 2 Bedrooms / sleeps 5

7 Nights min stay

Add to shortlist

from £99 / night

£690 - £750 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
Exceptional value for family holiday in Tuscany. Bright, modern, clean and easy to access. Two bedrooms, two bathrooms and lots of space inside and out.  …see more

24 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 6 Bedrooms / sleeps 12

Short stays welcome

Add to shortlist

from £232 / night

£1618 - £2518 / week

View

Key info:

  • Nearest beach 23 km
  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury Tuscan Villa . Villa for family reunions in Tuscany and for those looking for a stylish retreat.  …see more

18 Photos

Province of Arezzo / Castiglion Fiorentino

House / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £64 / night

£447 - £493 / week

View

Key info:

  • Nearest beach 23 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
The freshness of this charming garden apartment offering space and easy access to many of Tuscany's hill towns, vineyards and festivals., makes it a good choice for families (or friends) looking for something special and a lovely home in Tuscany  …see more

Excellent 5/5 

24 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 11

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £152 / night

£1064 - £2554 / 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

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

We've updated our Privacy Policy. You can read it here.