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Featured Holiday Homes in Castiglion Fiorentino

Welcome to Sarteano Look forward to a holiday in Italy.

Welcome to Sarteano Look forward to a holiday in Italy.

Sarteano
With a stay at this vacation home in Sarteano, you'll be on a lake, just steps from Val di Chiana and a 4-minute drive from Archaeological Museum of ...
Welcome to Sarteano Look forward to a holiday in Italy.
Casa delle Rose: charming house with stunning balcony in the heart of Cortona

Casa delle Rose: charming house with stunning balcony in the heart of Cortona

Cortona
With a stay at this vacation home in Cortona (Cortona Old Town), you'll be within a 15-minute drive of Lake Trasimeno and Cortona Cathedral.
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
Podere Casorbica with free parking, large garden, swimming pool.

Podere Casorbica with free parking, large garden, swimming pool.

cortona
Located in Cortona, this vacation home is in a rural location, a 4-minute drive from Santa Maria delle Grazie and 5 minutes from Cortona Cathedral.
Podere Casorbica with free parking, large garden, swimming pool.
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Villa Vallorsaia with private pool, lake view, no neighbors

Villa Vallorsaia with private pool, lake view, no neighbors

sansepolcro
With a stay at this vacation home in Sansepolcro, you'll be 4 mi (6.4 km) from Church of San Francesco and 4 mi (6.4 km) from House of Piero della ...
Villa Vallorsaia with private pool, lake view, no neighbors
Casa Fontelunga Tuscan holiday villa with private pool

Casa Fontelunga Tuscan holiday villa with private pool

cortona
Located in Cortona, this vacation home is in a rural location, within a 15-minute drive of Santa Maria delle Grazie and Cortona Cathedral.
Casa Fontelunga Tuscan holiday villa with private pool
The House Of Antonella Casentino, Arezzo, Tuscany, Italy

The House Of Antonella Casentino, Arezzo, Tuscany, Italy

Subbiano
Located in Subbiano, this vacation home is in the mountains, within a 15-minute drive of Arno River and Castle of the Fioraia.
The House Of Antonella Casentino, Arezzo, Tuscany, Italy
I Poggi di Belvedere

I Poggi di Belvedere

Pieve Santo Stefano AR
With a stay at this vacation home in Pieve Santo Stefano, you'll be 6.2 mi (10 km) from Museo Civico and 6.3 mi (10.1 km) from Little Museum of the Diary.
I Poggi di Belvedere
Villa with pool and garden

Villa with pool and garden

Città di Castello
When you stay at this vacation home in Città di Castello, you'll be 14 minutes by car from Tiber River.
Villa with pool and garden
La Dolce Collina

La Dolce Collina

VOC. CANTAGALLINA, 6, Castiglione del Lago, PG
Located in Castiglione del Lago, La Dolce Collina is in a rural location, within a 10-minute drive of Torre Beccati Quest'Altro and Chiusi Lake.
La Dolce Collina
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Castiglion Fiorentino Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Castiglion Fiorentino vacation homes are the perfect way for you to wing it.

Holiday houses in Castiglion Fiorentino let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Castiglion Fiorentino in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Castiglion Fiorentino adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Castiglion Fiorentino with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Castiglion Fiorentino vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Castiglion Fiorentino Holiday Homes essential information

Accommodation
1198 Holiday Homes
Lowest Price
AU$140
Highest Price
AU$666
Popular accommodation
Welcome to Sarteano Look forward to a holiday in Italy., Casa delle Rose: charming house with stunning balcony in the heart of Cortona, Podere Casorbica with free parking, large garden, swimming pool., Villa Vallorsaia with private pool, lake view, no neighbors, Casa Fontelunga Tuscan holiday villa with private pool, The House Of Antonella Casentino, Arezzo, Tuscany, Italy , I Poggi di Belvedere, Villa with pool and garden, La Dolce Collina

Top trending hotels in Castiglion Fiorentino

Farmhouse in the hills with panoramic view and swimming pool

Farmhouse in the hills with panoramic view and swimming pool

Ristonchia
Located in Castiglion Fiorentino, this vacation home is in a rural location, within a 10-minute drive of Tennis Club Castiglionese and Archaeological ...
Farmhouse in the hills with panoramic view and swimming pool
Charming Stone House in Castiglion Fiorentino: Your perfect Tuscan Getaway!

Charming Stone House in Castiglion Fiorentino: Your perfect Tuscan Getaway!

Castiglion Fiorentino
Located in Castiglion Fiorentino, this vacation home is in a rural location, within a 5-minute drive of Vasari Loggia and Municipal Art Gallery.
Charming Stone House in Castiglion Fiorentino: Your perfect Tuscan Getaway!
Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux

Località Borro, 1, San Giustino Valdarno, Loro Ciuffenna, AR
Fully refundableReserve now, pay when you stay
The price is AU$666 per night from 25 Nov to 26 Nov
AU$666
includes taxes & fees
25 Nov - 26 Nov
Located in Loro Ciuffenna, Il Borro - Relais & Châteaux is in the historical district, a 4-minute drive from La Salceta Winery and 6 minutes from Church of ...
Il Borro - Relais & Châteaux
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Hotel Minerva

Hotel Minerva

4 out of 5
Via Fiorentina, 4, Arezzo, AR
Fully refundableReserve now, pay when you stay
The price is AU$140 per night from 22 Dec to 23 Dec
AU$140
includes taxes & fees
22 Dec - 23 Dec
A stay at Hotel Minerva places you in the heart of Arezzo, within a 5-minute drive of San Donato Hospital and Centro Chirurgico Toscano.
Hotel Minerva
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.