List your home
Apply filters
£ to

Holiday homes 47

Reset search

Show results on map

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
Brolio
8 properties
Montecchio Vesponi
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
47 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 £146 / night

£1022 - £1971 / 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

100 Photos

Province of Arezzo / Castiglion Fiorentino

House / 2 Bedrooms / sleeps 6

Short stays welcome

Add to shortlist

from £131 / night

£912 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
3-room "Granaio", house, detached, for 6 people, 90 m2 on 2 levels, comfortable and cosy furnishings. Living/dining room with local TV. Smoking not allowed. Internet (Wireless LAN [WLAN]). 1 double sofa bed. Sleeping room with 1 double bed. Sleeping room with 2 single  …see more

100 Photos

Province of Arezzo / Castiglion Fiorentino

House / 2 Bedrooms / sleeps 5

Short stays welcome

Add to shortlist

from £109 / night

£763 - £1800 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
4-room apartment "Fienile", for 5 people, 70 m2, on the upper floor, comfortable and cosy furnishings. Living room with local TV and open fireplace. Smoking not allowed. Internet (Wireless LAN [WLAN]). 1 double sofa bed. Sleeping room with 1 double bed. Sleeping room  …see more

Featured properties

15 Photos

Province of Arezzo / Castiglion Fiorentino

Barn / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £120 / night

£834 - £906 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa Manciano is the ideal place to stay in Tuscany, for relax and also for daily drives into the best places of Tuscany and Umbria  …see more

100 Photos

Province of Arezzo / Castiglion Fiorentino

House / 1 Bedroom / sleeps 4

Short stays welcome

Add to shortlist

from £40 / night

£280 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
2-room semi-detached house 40 m2, on the ground floor, fully renovated, beautiful and tasteful furnishings: living/dining room with 1 double sofabed and satellite TV. 1 double bedroom. Kitchenette (4 hot plates, oven) with dining table. Shower/bidet/WC. Garden, porch. T  …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 £42 / night

£290 / 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

11 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 2 Bedrooms / sleeps 6

2 Nights min stay

Add to shortlist

from £37 / night

£256 / 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

Excellent 5/5 

24 Photos

Province of Arezzo / Castiglion Fiorentino

Farmhouse / 2 Bedrooms / sleeps 6

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £44 / night

£307 - £384 / 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


6 May 2014

5/5

"Clean, modern house situated near excellent wine destinations"

Our hostess was very nice. We arrived the day after Easter and she made a plate of traditional Tuscan snacks for us upon our arrival. The house was spacious, clean, and modern. Internet connection was… More


5 Aug 2014

5/5

"Alles in Ordnung"

Wir waren im Juli leider nur für 3 Tage hier. Das Haus ist sauber und groß, es gibt zudem einen riesigen Außenbereich und eine himmlische Ruhe. Die Gastgeber sind super freundlich und zuvorkommen… More


24 Aug 2015

5/5

"Lovely accommodation"

The accommodation is very welcoming, clean and comfortable. We experienced extremely hot weather and found the air conditioning in the bedrooms a great bonus. The location is restful and secure. Ma… More

See all reviews Continue

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 £163 / night

£1135 - £2300 / 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


6 Jun 2013

5/5

"Just wonderfull"

Going to Daniele’s villa on the mountain in Castiglion Fiorentino is a great experience, once I experienced it, I fell in love with the place, the atmosphere and the hospitality of the host. It is t… More


20 May 2013

5/5

"Simply couldn't be better!"

We will be returning here for the sixth time this year. Danielle is the perfect host and our return always feels like a 'coming home'. Nothing is too much trouble for him. The house is well equippe… More

See all reviews Continue

Excellent 5/5 

24 Photos

Castiglion Fiorentino / Orzale

Villa / 2 Bedrooms / sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £79 / night

£548 - £1088 / 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


28 Jun 2015

5/5

"Fast zu schön, um wahr zu sein."

Am Hang gelegen ist die Aussicht bereits vom Frühstückstisch ein Traum. Am Tage hört man fast nur die Grillen zirpen und die Stille in der Nacht ist für uns Städter die pure Erholung. Das Haus is… More

See all reviews Continue

43 Photos

Castiglion Fiorentino / Brolio

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

Add to shortlist

from £629 / night

£4400 - £7000 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
Villa Colline Senesi is an old country residence, skilfully restored and transformed into an exclusive private retreat. Situated in the centre of Valdichiana, close to Arezzo and Cortona, the villa offers the possibility to quickly reach the main historical and artisti  …see more

40 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £862 / night

£6030 - £9045 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
nestling in the heart of the world-famous chianti valley, just thirty minutes from florence, stands castello  di ginevra. This graceful country residence is located near the ancient town of castelfiorentino and is steeped in history. Traces of the original 13th-centur  …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 £53 / night

£365 / 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 £47 / night

£329 - £563 / 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 

12 Photos

Province of Arezzo / Castiglion Fiorentino

House / 6 Bedrooms / sleeps 13

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £337 / night

£2357 - £3055 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • 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 ava  …see more


18 Jun 2015

5/5

"A TUSCAN DREAM"

Amazing idyllic home in a dreamlike setting. All the comforts of a modern home, in a centuries old house. Wonderful owners that know everything to do in the area. Food recommendations never disappoint… More


21 Apr 2013

5/5

"Charming, comfortable country villa, conveniently located."

Charming villa, comfortably accommodates 12 adults. Can be divided into 3 separate 2-bedroom apartments, each with its own kitchen/dining/bath and living area, or rented as one for use by a group. … More


4 Dec 2012

5/5

"Beautiful site"

This is a lovely villa located in the Tuscan country side outside Castiglione Fiorentino. The views of Cortona and castle Montechio lit up by the setting sun are marvelous. The gardens include a vin… More

See all reviews Continue

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 £152 / night

£1059 - £2322 / 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


6 Jul 2014

5/5

"Tuscany in a nutshell!"

What an incredible place! This villa has absolutely everything you need to make your stay in Tuscany a pleasant one. All rooms are big, clean and with typical furniture and the kitchen well equipped. … More


10 May 2014

5/5

"Villa Serene"

Villa Senaia was a truly wonderful experience so much so we return every two years with family & friends. The wonderful panoramic vista from the villa and pool is breath taking as it calming. Subtle h… More


26 Feb 2014

5/5

"A most warm welcome to a beautiful home"

With the hills of Tuscany and a church spire in the background, playing bocce or swimming in the pool said "we are no where else but Italy." Dining on the terrace overlooking the town of Castiglion-F… More

See all reviews Continue

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 £51 / night

£351 / 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


11 Nov 2013

5/5

"feeling at home away from home"

Last August we stayed with a group of friends at this beautiful farm house . The house ,steeped in history ,is located in the valley of Val de Chio , the vistas are truly amazing and the house is ve… More


14 Sep 2014

5/5

"Un bel soggiorno"

Capitati seguendo a grandi linee le indicazioni di un'articolo trovato su mototurismo.it, siamo stati accolti con cordialità ed estrema disponibilità, Maria e Rinaldo si sono dimostrati subito degli… More

See all reviews Continue

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 £42 / night

£292 - £406 / 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

Very Good 4.5/5 

16 Photos

Province of Arezzo / Castiglion Fiorentino

House / 2 Bedrooms / sleeps 4

Very Good 4.5/5 

1 night min stay

Add to shortlist

from £29 / night

£198 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
Casa indipendente comoda ideale per vacanze di famiglie, coppie, gruppi di amici. Vicina ai più importanti centri della Toscana e dell'Umbria Lago Trasimeno, Perugia, Cortona, Arezzo, Siena, Firenze. Soggiorni in città d'arte esperienze gastronomiche: vino e chianina  …see more


7 Apr 2015

5/5

"nel cuore della valdichiana"

Come dimenticare di aver dormito tra le mura di Porta Romana? ci siamo sentiti dentro un pezzo di medioevo.... curata, accogliente, pulitissima e punto di appoggio per le scorribande tra toscana del s… More

Grazie carissima Chiara, un saluto alla vostra bella e simpatica compagnia ed un bacione alla piccola! Mi devo complimentare io con voi per aver saputo scegliere, durante il vostro soggiorno, di visitare località meno conosciute ma molto molto affascinanti. Bravi, e complimenti a te che ti sei dimostrata una bravissima organizzatrice! Non mi resta che dire... alla prossima! ;)


13 Sep 2013

5/5

"Esperienza Meravigliosa"

Abbiamo avuto il piacere di soggiornare una settimana nel mese di agosto, in questa deliziosa casa d'epoca ristrutturata e molto accogliente, spaziosa e ben curata ubicata in un contesto m… More

E' stato un piacere per me ricevere la vostra bella e simpatica famiglia nella mia casa. Mi fa piacere che vi siate trovati bene, vi ringrazio molto per le belle parole che avete voluto avere per commentare la vostra vacanza. Mi complimento con voi per la scelta delle escursioni che avete scelto di fare, avete saputo scegliere angoli suggestivi della nostra terra, con competenza e capacità che non sono comuni. Aspettando di incontrarvi di nuovo a Castiglion Fiorentino, vi saluto cordialmente e rimango a vostra disposizione Ilaria


27 Aug 2013

5/5

"Un'esperienza unica!!!"

Ho soggiornato con la mia famiglia a Le antiche Scale dal 7 al 15 agosto 2013...un'esperienza indimenticabile. Ilaria, la padrona di casa, è molto gentile e disponibile. La casa è carina, ricavata n… More

Cara Sabina, grazie per il suo commento, sono contenta che la sua vacanza sia stata felice nella nostra casa. Sono orgogliosa di aver accontentato una persona come lei, una storica dell'arte che ama la propria professione e sa scegliere il meglio per le sue vacanze nelle città d'arte. Aspetto lei e la sua famiglia per farle assaporare la stagione invernale in Toscana, che ha colori e situazioni altrettanto affascinanti quanto quella estiva. Saluto lei, suo marito ed i suoi cari e simpatici " birichini" ! Ilaria

See all reviews Continue

8 Photos

Province of Arezzo / Castiglion Fiorentino

B&B / 1 Bedroom / sleeps 3

1 night min stay

Add to shortlist

from £54 / night

£373 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Bed and breakfast Boscatello situato a Castiglion Fiorentino,tra Cortona e Arezzo, nel cuore di Toscana.  …see more

24 Photos

Province of Arezzo / Castiglion Fiorentino

Farmhouse / 4 Bedrooms / sleeps 10

3 Nights min stay

Add to shortlist

from £141 / night

£986 / 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  …see more

18 Photos

Province of Arezzo / Castiglion Fiorentino

B&B / 6 Bedrooms / sleeps 12

1 night min stay

Add to shortlist

from £63 / night

£438 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Bed & Breakfast with pool and oasi relax  …see more

21 Photos

Castiglion Fiorentino / Montecchio Vesponi

House / 4 Bedrooms / sleeps 11

6 Nights min stay

Add to shortlist

from £84 / night

£584 - £1497 / 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 £47 / night

£329 / 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 £42 / night

£292 / 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

10 Photos

Province of Arezzo / Castiglion Fiorentino

Farmhouse / 7 Bedrooms / sleeps 13

1 night min stay

Add to shortlist

from £21 / night

£146 / week

View

Key info:

  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
CASA TIPICA TOSCANA CON TRAVI IN LEGNO E MEZZANE AMPIA TERRAZZA CON VISTA SULLA CAMPAGNA TOSCANA E DEL PAESE DI CASTIGLION FIORENTINO E CASTELLO DI MONTECCHIO.  …see more

16 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 1 Bedroom / sleeps 4

2 Nights min stay

Add to shortlist

from £26 / night

£176 / week

View

Key info:

  • Great 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

5 Photos

Castiglion Fiorentino / Montecchio Vesponi

Condo / 2 Bedrooms / sleeps 5

1 night min stay

Add to shortlist

from £37 / night

£256 - £475 / 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

18 Photos

Province of Arezzo / Castiglion Fiorentino

B&B / 3 Bedrooms / sleeps 2

1 night min stay

Add to shortlist

from £52 / night

£363 - £421 / 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

14 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 1 Bedroom / sleeps 4

1 night min stay

Add to shortlist

from £47 / night

£329 / 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

24 Photos

Castiglion Fiorentino / Montecchio Vesponi

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

Add to shortlist

from £365 / night

£2555 - £5110 / 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

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 £149 / night

£1043 - £1123 / 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


12 Sep 2013

5/5

"Perfekter Toskanaurlaub mit Freunden und Kindern"

Nach langer Anreise erwartete uns ein freundlicher Empfang und ein sehr netter Vermieter. Die Ausstattung des Hauses sowie des Geländes (Pool, Liegen, Gartenmöbel) sind hervorragend. Der Vermieter w… More


13 Jun 2013

5/5

"Un posto incantevole"

Un posto incantevole. La casa è molto bella e funzionale. Un vecchio casale del 1700 ristrutturato ma che conserva ancora il fascino del tempo. La casa è molto tranquilla, pulita e con tutti gli op… More


6 Sep 2013

4/5

"Echt Italie"

Een prachtig huis op een mooie plek. Rust, stilte, uitzicht. Het huis is ruim, schoon en prima verzorgd. Heerlijk zwembad. Je hebt een eigen auto nodig, want het huis ligt heerlijk afgelegen. Hier gaa… More

See all reviews Continue

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 £208 / night

£1453 - £1818 / 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


13 Mar 2013

5/5

"Lovely family vacation"

Clean, comfortable and spacious. These are important when choosing a vacation home and Daniella certainly has all of this. Te bedrooms are very comfortable, clean bathrooms, a full kitchen with just … More


17 Feb 2013

5/5

"Beautiful Setting, Fantastic View, Charming Host"

We have stayed at this villa 3 times and will be staying there again this May (2013). Our first stay was for 2 weeks in 2001. We were a party of 6 including my 80 year old mother. We appreciated th… More


11 Feb 2013

5/5

"exceptional place: Peaceful and our Perfect home form Home"

We did enjoy our two weeks here. It was home from home. Relaxed and care free. The property was clean and bright, everything for our needs. Of course, we do not have a pool at home - and this is what… More

See all reviews Continue

100 Photos

Province of Arezzo / Castiglion Fiorentino

House / 7 Bedrooms / sleeps 14

Short stays welcome

Add to shortlist

from £212 / night

£1481 - £2459 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
16-room house for 14 people, 600 m2 on 3 levels, antique and luxurious furnishings. Living/dining room with cable TV, DVD, radio, open fireplace, dining-table and dinette. Smoking allowed. 4 single beds and 5 double beds. Sleeping room with 1 double bed. Sleeping room  …see more

100 Photos

Province of Arezzo / Castiglion Fiorentino

House / 5 Bedrooms / sleeps 9

Short stays welcome

Add to shortlist

from £127 / night

£887 - £1748 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
7-room villa 300 m2 on 2 levels, on the ground floor. Renovated, simple and antique furnishings: entrance hall. Living room with TV (flat screen). Dining room with dining table. Kitchenette (4 hot plates, oven, dishwasher, microwave, freezer) with dining table. Upper fl  …see more

13 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 1 Bedroom / sleeps 3

3 Nights min stay

Add to shortlist

from £44 / night

£307 / 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 

15 Photos

Province of Arezzo / Castiglion Fiorentino

Apartment / 2 Bedrooms / sleeps 5

Excellent 5/5 

Short stays welcome

Add to shortlist

from £68 / night

£475 - £687 / 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


18 Aug 2014

5/5

"The perfect holiday."

What a wonderful place to stay in the beautiful Tuscan countryside. I cannot offer enough praise for Villa Maria and our fantastic hosts Maria and Rinaldo. The house is located on the side of a hill … More


12 Sep 2013

5/5

"Lovely old rustic villa with great views."

Myself and three friends had a wonderful four weeks staying in the Villa Maria. The position of the villa is on a hillside with stunning views across the valley. The town of Castiglion Fiorentino is o… More


30 Jul 2013

5/5

"Absolutely gorgeous!"

We had the best time at Maria's beautiful place! Very nice apartment with two large and bright bed rooms, fans and mosquito nets at the windows (yeah!!). The surroundings were absolutely stunning, sit… More

See all reviews Continue

Excellent 5/5 

24 Photos

Province of Arezzo / Castiglion Fiorentino

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £98 / night

£685 - £725 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Grazia has all the warm characteristic of an ancient Tuscan farmhouse. The renovation, has been completed retaining all original features. High-ceilings with chestnut beams, and terra-cotta floors set the seen of this cosy family vacation home.  …see more


15 May 2013

5/5

"A place in the sun and relaxing!"

I stayed at this villa for a week with my friends. The building is historic and so charming and it has a character. We liked the decoration in the rooms and very clean. Wifi was very useful to have, t… More


5 May 2013

5/5

"Perfect location for company retreat or working holiday: writing, thinking, walking, etc"

I needed a place to host a week of brainstorming and team-building for myself and a small group of people in my company. I was lucky enough to come across this one and it turned out to be more than I … More

Thanks for choosing our villa and for staying with us. We really do appreciate it - and, thank you for taking the time to let us know what you thought of our accommodations. We look forward to welcoming you here again one day. Our very best wishes


20 May 2013

5/5

"Ein gelungener, erholsamer und interessanter Urlaub."

Das antike Haus ist sehr bequem eingerichtet, sauber und gepflegt. Mein Mann und ich waren dort mit drei Freunden. Wir haben die Großzügigkeit und die Möglichkeiten dieses wunderschönen Landhauses… More

See all reviews Continue

Excellent 5/5 

23 Photos

Castiglion Fiorentino / Orzale

Condo / 1 Bedroom / sleeps 2

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £64 / night

£442 - £538 / 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


21 Apr 2014

5/5

"Romantic Lovely and Memorable Honeymoon"

Thank you Terry for the opportunity to stay at Orzale and the little cottage. It was wonderful. After a few days in Venice and then Modena, the little cottage was a great place for us to enjoy the las… More

See all reviews Continue

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 £82 / night

£573 - £606 / 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


27 Jul 2013

5/5

"our family are happy to have found the little village"

we have enjoyed our holidays to Tuscany for the last four years and chose to stay here for a second year. The cottage (le Stella) has lots of space for us and, the additional studio attached was very … More


27 Sep 2012

5/5

"Romantic, clean cottage, splendid view, lovely silence; unique location."

Whenever we plan a vacation we have following criteria in mind: comfortable, clean housing, privacy, far from all noise, nice view, close to cultural highlights, pleasant climate, swimming facility. N… More

Greetings Tinus and Jeanne It seems a while ago now, but happy memories of meeting the two of you and our many conversations. We are so very pleased that your 8 nights at Il Borgo recharged your batteries and gave you so much pleasure. We really do look forward to seeing you both again. THis coming year, the owners are planning many improvements which should make your return even more enjoyable. Our very best wishes to you both.


10 Aug 2012

5/5

"Top value, an enjoyable experience"

We all agreed, nice cottage. everything you need, you find in the kitchen. very nice pool 30 meters from the cottage. Perfect customer service from the owner incl. information about the traveling and … More

See all reviews Continue

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 £76 / night

£526 - £577 / week

View

Late Deal: save up to €191 (approx. £138)

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


4 Sep 2014

5/5

"Happy Holiday!"

First thanks to Rosino for a warm welcome to our family and the extra help they gave us with our plans and tours. Plus the nice touches of fresh fruit, olive oil and one when we arrived - all very kin… More


29 Jun 2013

5/5

"The Great Escape!"

Take three children and introduce them to Italy..... One week touring around the Amalfi and the other in Tuscany. Here we had our "real" family vacation and enjoyed this country retreat with its pool… More


23 Jun 2013

5/5

"great family vacation, lots to do and see"

This was a last minute family vacation, and we wanted to be in the Tuscan countryside and to experience some of the places we read about in the Tuscan Sun book. The cottage La Stelle was perfect for t… More

See all reviews Continue

Very Good 4/5 

24 Photos

Province of Arezzo / Castiglion Fiorentino

Cottage / 3 Bedrooms / sleeps 5

Very Good 4/5 

Short stays welcome

Add to shortlist

from £76 / night

£526 - £606 / week

View

Late Deal: save up to €176 (approx. £128)

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


3 Oct 2011

5/5

"A Taste of Tuscan Tranquility"

We found this wonderful little house by chance while on a touring holiday in September 2011. The owners were very helpful in accomodating us for a last minute booking & prepared the house in a matter … More


25 May 2011

5/5

"Lovely place full of character."

From each room there is a great view and our small terrace was perfect for us to eat and relax. Rooms were clean and cosy, pretty much all we needed for the week. The main town is a drive away (4 mi… More


15 May 2011

5/5

"Relaxation for us adventure for the kids!"

An inexpensive find in Tuscany. A two-week stay here in august 2011 proved better than anticipated. It has lots of charm and its setting meant that my wife and I were able to relax, catch up on a fe… More

See all reviews Continue

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 £71 / night

£497 - £714 / 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


3 Apr 2015

5/5

"Just as green as Ireland - but with sunshine!"

We enjoyed our two weeks here and found the villa clean, comfortable and in a good location. It was easy to walk along to the local shop. bar and - a little further up a family restaurant. Great view… More


3 Apr 2015

4/5

"A warm welcome and a great time for us"

We are late to thank Maria and Terry for their help in making our vacation plans and for their warm welcome. Our cottage/apartment here was just what we expected -clean, comfortable and fantastic vie… More

See all reviews Continue

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 £326 / night

£2280 - £3570 / 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

Very Good 4/5 

21 Photos

Province of Arezzo / Castiglion Fiorentino

Cottage / 2 Bedrooms / sleeps 4

Very Good 4/5 

1 night min stay

Add to shortlist

from £73 / night

£508 / week

View

Key info:

  • Swimming pool
  • Suitable for children over 5
  • Some pets are welcome - please contact the owner
  • Private garden
Tuscany, Private pool, value,  …see more


24 Aug 2015

4/5

"Peace and tranquility"

We had a great time, the pool was most welcome and the peace and tranquility much appreciated (only noise was the chickens next door!). It is quite remote but the stars were great and we even saw … More

See all reviews Continue

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 £157 / night

£1095 - £2628 / 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