Holiday rentals in Castiglion Fiorentino

Farmhouse Fattoria La Parita

Provencal style apartment surrounded by vineyard and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 from the highway. The singing of the acorn and cuckoo will be the soundtrack to the living room while the roe deer burn among the olive trees. An Italian basic breakfast (coffee, tea, milk, cookies, etc.) is included, if you prefer a richer and served breakfast at the table, the cost is €15 per person (€10 from 5 to 15 years, free less than 5 years old). Wallbox EV available.

"Borgo Sant'Andrea al Pozzo" in Ancient Abbey

Completely renovated residence within an ancient Abbey, already mentioned in 1114 A.D. and owned by the Camaldolese friars in the 12th century. A few meters from the historic walls of Castiglion Fiorentino dating back to 1200 AD and Porta Romana. It is a 500-meter walk from the historic center of Castiglion Fiorentino and a 15-minute drive from Cortona. A unique stay, between history and nature, in a relaxing and reserved setting. Strategic point for visiting Siena, Pienza, Anghiari, Arezzo, Cortona...

Casa Letizia apartment in the historic center

Delightful apartment in a medieval historic building, in the historic center of Castiglion Fiorentino, a stone's throw from the Cassero tower and the Vasari Loggia, on Corso Italia. Close to a wine shop, pizzeria, shops, restaurants, clubs and bars located in the center, next to services (bank, post office, offices). Just a 2-minute walk to the parking lot right outside the walls. Close to the train station (about 800 meters) Close to bus station (about 150 meters). Free public parking 50 m away.

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Tuscan charm of villa - countryside

Nell’affascinante campagna Toscana,tra ulivi e vigneti una villa in pietra,in posizione strategica per cogliere i segreti di Toscana e Umbria aria condizionata e piscina con area wellness per il vostro relax e confort Villa Senaia è una grande casa con travi in ​​legno, in una splendida posizione in collina con vista idilliaca che affaccia su uno dei luoghi preferiti della campagna toscana, un ambiente attraente per mangiare all'aperto, bevendo vino toscano e ascoltando i grilli e le cicale

Casale Santa Barbara - Exclusive Apartment

At a glance: • Location: perfect entry door to the Val d’Orcia between Pienza (8,5 km) and Montepulciano (8,5 km). • Charming warm old stones Tuscan house – completely restored in 2016 • Big apartment (100m2), designed for 2 persons, completely independent, fully furnished, Tuscan style with modern equipment. • Exclusivity: we are living on the 1st floor; the ground floor is yours. You are our only guests. • Spacious private garden (+ 300m2) • Stunning view on the Tuscan hills.

Green – The meadows in Tuscany

Apartment consisting of 1 double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we provide the washing machine from 9 a.m. to 8 p.m. which is in our laundry room for those who request it). We recommend the car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and wifi Strategic location for visiting Tuscany and Umbria.

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Pendici 15, small apartment

Cozy apartment inside a stone cottage where you can enjoy the atmosphere of the Tuscan countryside and at the same time the proximity to the historic center of Castiglion Fiorentino. Ideal for couples, families and travelers with four-legged friends, it is the ideal starting point for visiting Tuscany. The accommodation combines the rustic charm of stone houses with modern comforts, offering a relaxing stay in a quiet and panoramic setting.

CasaNella: bright, central and panoramic

Cozy, elegant and delightful apartment in the center of Cortona, with an enchanting view that sweeps from Lake Trasimeno to Valdichiana. Carefully furnished, it is the ideal place to spend a few days in this wonderful town. A short walk from the main road, but in a quiet and panoramic location. Free parking is a short distance away. Equipped with heating and air conditioning. High speed WiFi available. Great for smart working.

Casa del Passerino

Apartment located inside a historic building in Cortona, dating back to the 1500s, overlooking the city's main square... Our property, while condemning the war, dissociates itself from all racist behavior towards the Russian and Belarusian population. At Casa del Passerino, people of these nationalities are welcome and will be treated the same as everyone else. We look forward to seeing you in Tuscany!