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Featured Holiday Homes in Castiglion Fiorentino

Villa with Pool, Spa, and Relaxation: A Paradise between Umbria and Tuscany

Villa with Pool, Spa, and Relaxation: A Paradise between Umbria and Tuscany

Umbertide
Located in Umbertide, this vacation home is in a rural location, within a 15-minute drive of Santa Croce Museum and Church of Santa Maria della Reggia.
Villa with Pool, Spa, and Relaxation: A Paradise between Umbria and Tuscany
Enchanting tuscan house, private garden, wellness, stunning views, easy to reach

Enchanting tuscan house, private garden, wellness, stunning views, easy to reach

San Giovanni d'Asso
A stay at this vacation home places you in the heart of Montalcino, within a 5-minute drive of Museo del Tartufo and San Giovanni d'Asso Station.
Enchanting tuscan house, private garden, wellness, stunning views, easy to reach
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga

Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga

cortona
Located in Cortona, this vacation home is in a rural location, a 4-minute drive from Santa Maria delle Grazie and 6 minutes from Cortona Cathedral.
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga
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Agriturismo Nestore

Agriturismo Nestore

Via del Tegolaio, Umbertide, PG
Located in Umbertide, Agriturismo Nestore is within a 15-minute drive of Tiber River and Laghi di Faldo.
Agriturismo Nestore
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
Villa with swimming pool and garden- San Feliciano, Trasimeno lake

Villa with swimming pool and garden- San Feliciano, Trasimeno lake

San Feliciano
When you stay at this vacation home in Magione, you'll be near the beach, within a 15-minute walk of Lake Trasimeno and Zocco Castle.
Villa with swimming pool and garden- San Feliciano, Trasimeno lake
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
Typical Tuscan Residence near the farm la Vialla

Typical Tuscan Residence near the farm la Vialla

Ponina
Located in Capolona, this vacation home is in the mountains, within a 15-minute drive of Castle of the Fioraia and Pieve di San Martino Sopr'Arno.
Typical Tuscan Residence near the farm la Vialla
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Montepulciano
A stay at this vacation home places you in the heart of Montepulciano, steps from Val di Chiana and 4 minutes by foot from Cantina Contucci.
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
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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
1380 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Villa with Pool, Spa, and Relaxation: A Paradise between Umbria and Tuscany, Enchanting tuscan house, private garden, wellness, stunning views, easy to reach, Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga, Agriturismo Nestore, Casa Fontelunga, Tuscan holiday villa with private pool, Villa with swimming pool and garden- San Feliciano, Trasimeno lake, Farmhouse in the hills with panoramic view and swimming pool, Typical Tuscan Residence near the farm la Vialla, INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

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
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10, Montepulciano, SI
Fully refundableReserve now, pay when you stay
Located in Montepulciano, Precise Tale Poggio Alla Sala is in a rural location, a 1-minute drive from Val di Chiana and 7 minutes from Terme Sant'Elena.
Precise Tale Poggio Alla Sala
Nuovo Etruria Resort

Nuovo Etruria Resort

Via di S. Martino snc, Montepulciano, SI
Fully refundableReserve now, pay when you stay
With a stay at Nuovo Etruria Resort in Montepulciano, you'll be a 1-minute walk from Val di Chiana and 14 minutes by foot from Church of St. Agnes.
Nuovo Etruria Resort
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Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6, Cortona, AR
Fully refundableReserve now, pay when you stay
When you stay at Villa di Piazzano - Small Luxury Hotel of the World in Cortona, you'll be in the historical district and 7.6 mi (12.2 km) from Lake ...
Villa di Piazzano - Small Luxury Hotel of the World
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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.