List your home
Apply filters
£ to

Holiday homes 23

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: City breaks (23)

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
23 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 £141 / night

£986 - £1902 / week

View

Key info:

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


26 Jul 2014

5/5

"A wonderful place"

We had a wonderful week in the villa in Rigutoni. It is a beautiful setting. Sitting in front of the villa for dinner at night, which we did every night bar one when there was spectacular rain and a t… More


8 Aug 2014

5/5

"VACANZA INDIMENTICABILE DA RIPETERSI L'ANNO PROSSIMO"

la villa è stupenda, i posti sono meravigliosi! abbiamo fatto una vacanza indimenticabile da ripetersi assolutamente perché i posti da vedere sono tanti, e poi al Querciolo si sta proprio bene, imme… More


29 Oct 2013

5/5

"Esperienza fantastica!"

Questa estate io e un gruppo di amici abbiamo deciso di prendere in affitto questa casa per due settimane, ed è stata un'esperienza da consigliare a chiunque sia in cerca di un rifugio dallo stress c… More

See all reviews Continue

Excellent 5/5 

19 Photos

Castiglion Fiorentino / Montecchio Vesponi

B&B / 6 Bedrooms / sleeps 12

Excellent 5/5 

1 night min stay

Add to shortlist

from £61 / night

£423 - £493 / 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. Our  …see more


30 Apr 2015

5/5

"Che meraviglia!!!!!!!!!!!!"

Io e mio marito abbiamo trascorso il weekend di Pasqua presso questo nuovissimo Bed & breakfast appena ristrutturato. La struttura tipicamente Toscana si trova a pochi passi da Cortona e x noi è stat… More

See all reviews Continue

20 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 2 Bedrooms / sleeps 3

3 Nights min stay

Add to shortlist

from £46 / night

£317 - £423 / 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

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 £41 / night

£282 - £391 / 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


29 Apr 2015

5/5

"...migliore della prima volta!"

Sono ritornata presso questa struttura per la seconda volta. C'ero stata con mio marito e due figli adolescenti lo scorso anno che aveva appena aperto e eravamo stati magnificamente, ma questa volta … More


4 Sep 2014

5/5

"The right place to enjoy your holiday"

I've spent five days at Le Finestre di San Michele with a Group of friends. The apartment is really nice, big, confortable and with a huge view. The owner and her daughter are so kind and friendly. We… More

I'm really happy to hear you spent nice days at Le finestre di San Michele. Looking forward to seeing you again I'm going to prepare some other fruit jams and juices to submitt to your judgement. Thank you Maria Rita


10 Sep 2014

5/5

"old town house a Castiglion Fiorentino"

ho soggiornato nell'appartamento "le finestre di San Michele " con 4 amici durante le feste per il patrono. L'appartamento, molto accogliente, spazioso, luminoso è arredato con cura, funzionalità e … More

Sono felice di sapere che avete trascorso dei bei giorni a Castiglion Fiorentino . Spero che il prossimo anno il Rione di Porta Romana vinca il Palio così da permettervi, se tornerete, di partecipare anche alla festa della vittoria che si tiene proprio nella piazza sotto casa (incrociamo le dita). Vi ringrazio per aver scelto Le finestre di San Michele per il vostro soggiorno a Castiglion Fiorentino e spero che ne parlerete con i vostri amici. Grazie Maria Rita

See all reviews Continue

Excellent 5/5 

18 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 5 Bedrooms / sleeps 12

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £91 / night

£634 - £1353 / 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


13 May 2015

5/5

"very good house to rent"

the place is beautiful! there is full of peace and incredible landscape around the house! very good swimming pool, there is also a Iacuzzi swimming pool with warm water! it is a very confortable hous… More


13 May 2015

5/5

"good place at good price"

it was the first time, we come in italy, we have rent this house because good price and there is a lot of bedrooms!! the owners is very friendly, we have free wifi connection in the house, the swimmin… More


12 May 2015

5/5

"I love this place!"

It was a very relaxing holiday! the house and the countryside give us peace and quiet. it was an hot week, but the house was fresh and breezy. the swimming pool is very nice and there is a beautiful… More

See all reviews Continue

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 £51 / night

£353 / 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


18 Sep 2014

5/5

"A perfect place for a wonderful and leasurely vacation!"

This was a perfect 2 week stay for me and 4 of my friends. Very well maintained place, clean apartment, very helpful and responsive staff. It has nice amenities and it is a good spot for a base of you… More

See all reviews Continue

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

£317 - £543 / 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


24 Nov 2014

5/5

"Une petite merveille..."

Nous avons séjourné dans cette jolie maison en pierre typiquement Toscane, au charme fou, maison située dans un cadre absolument magnifique, des oliviers à perte de vue, un jolie jardin bien fleur… More

See all reviews Continue

Excellent 5/5 

15 Photos

Castiglion Fiorentino / Montecchio Vesponi

Studio / sleeps 3

Excellent 5/5 

Min stay varies

Add to shortlist

from £36 / night

£247 / week

View

Key info:

  • Nearest beach 150 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Big and bright studio apartment in Montecchio Vesponi, Castiglion Fiorentino with parking and WiFi  …see more


15 Apr 2014

5/5

"Beautiful, tranquil location with plenty of nearby attractions."

Owners very welcoming and hospitable. They could not do enough to make sure we were comfortable. They even came out to rescue us on two occasions when we couldn't find our way back! Spacious accom… More

Thank you Margaret! It was lovely to meet you and Steve and we hope you both have a fabulous Easter. Hope to see you again one day, either here in Tuscany or in your part of the woods. xxx

See all reviews Continue

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 £39 / night

£268 - £282 / 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 Nov 2013

5/5

"Esperienza fantastica!!!"

Abbiamo trascorso un lungo fine settimana a casa di Claudia, è stata un'esperienza fantastica! la casa è bellissima e dotata di tutti i confort, si trova in un vicolo del centro storico...una merav… More

...e noi siamo qui ad aspettarvi! Il Capodanno è già organizzato con antipasti toscani, primi e .....FIORENTINA!!


20 Jul 2013

5/5

"Ottima Scelta!: Molto Pulito e Spazioso + Posizione Centrale"

In pieno centro storico ma con comodo parcheggio gratis per auto nelle immediate vicinanze.La zona del centro in cui è ubicato è molto silenziosa e immersa nella tranqullità più completa. Apparta… More


27 Jun 2013

5/5

"bellissima esperienza"

L’appartamento si presenta davvero bene: pulito, ordinato ed arredato in modo congruo per soddisfare le reali necessità di una famiglia in vacanza (senza particolari fronzoli, per intenderci). Molt… More

See all reviews Continue

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 £81 / night

£564 / 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


18 Aug 2014

5/5

"Excellent"

Excellent welcome, beautiful garden with playground and barbecue, owners available. We ave the dog with us and we really enjoyed. Magnificent and peaceful palce..... next year we are here.....… More


14 May 2015

5/5

"Relax all'ombra di Castel Fiorentino"

La Casa delle Rose é la location perfetta x chi cerca un oasi per il relax...vi troverete immersi nella tranquilla campagna toscana,all'ombra dello splendido borgo di Castel Fiorentino. Ottima logist… More

See all reviews Continue

11 Photos

Castiglion Fiorentino / Orzale

Townhouse / 2 Bedrooms / sleeps 5

Min stay varies

Add to shortlist

from £46 / night

£317 - £529 / 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

£247 / 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 £58 / night

£405 / 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

23 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 1 Bedroom / sleeps 2

5 Nights min stay

Add to shortlist

from £67 / night

£469 / 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

21 Photos

Castiglion Fiorentino / Montecchio Vesponi

House / 4 Bedrooms / sleeps 11

6 Nights min stay

Add to shortlist

from £81 / night

£564 - £1444 / 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

7 Photos

Province of Arezzo / Castiglion Fiorentino

Townhouse / 2 Bedrooms / sleeps 5

2 Nights min stay

Add to shortlist

from £46 / night

£317 / 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

12 Photos

Province of Arezzo / Castiglion Fiorentino

Guest house / 1 Bedroom / sleeps 3

3 Nights min stay

Add to shortlist

from £41 / night

£282 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
In the historical centre of Castiglion Fiorentino in a quiet area is this independant Tuscan style one bedroom home with amazing views of the the Tuscan landscape and a private outside courtyard. Perfect base to explore Tuscany and Umbria  …see more

12 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 2 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £36 / night

£247 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
B&B val di chio, B&B val di chiana, Casa vacanze Arezzo, casa vacanze val di chio, casa vacanze val di chiana, casa vacanze Toscana, Casa vacanze Castiglion Fiorentino.  …see more

14 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 1 Bedroom / sleeps 4

1 night min stay

Add to shortlist

from £46 / night

£317 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Historical Centre Apartment + terrace in centre WIFI  …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

£353 - £409 / 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

24 Photos

Castiglion Fiorentino / Montecchio Vesponi

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

Add to shortlist

from £353 / night

£2465 - £4930 / 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

13 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 1 Bedroom / sleeps 3

3 Nights min stay

Add to shortlist

from £43 / night

£296 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Large Sunny Studio aprtment in Historical Centre with Garden and Wifi  …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 £151 / night

£1057 - £2536 / 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


6 Jul 2014

5/5

"Beauty and peace"

We just returned from an amazing week at Villa Villibona. The location is secluded and peaceful with breathtaking views but still a short drive to town and many nearby towns (car is a must). The pict… More


2 Aug 2012

5/5

"totale ruhe"

wir verbrachten dort 3 wochen im juli 2012. alles war perfekt. andrea und seine mutter kuemmerten sich um jeglichen belang. die sprichwoertliche toskanische gastfreundschaft wurde hier mehr als ueberb… More

See all reviews Continue

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