Holiday rentals in Castiglion Fiorentino

4.99 out of 5 average rating, 420 reviews

Farm stay in Ruscello

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 €10 per person (€6 from 5 to 15 years, free less than 5 years old). Wallbox EV available.

4.98 out of 5 average rating, 56 reviews

"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...

Home in Castiglion Fiorentino

4.94 out of 5 average rating, 81 reviews

The small tower

The proposed farmhouse is a typical townhouse made of characteristic Tuscan stone, ideal for those who want to spend relaxing vacations surrounded by the green hills of Castiglione that surround the small valley of Chio. The turreted accommodation is on three levels: the usable portion of the building is on the first floor with a living/dining room and an equipped kitchen and on the second floor with a double bedroom, a twin bedroom and a bathroom with shower, all furnished with period furniture.

4.99 out of 5 average rating, 155 reviews

Flat in Cortona

Cortona’s Rooftop Nest

L’appartamento è sito in pieno centro storico proprio di fronte alla meravigliosa chiesa di San Francesco e a pochi passi dalla piazza principale.Arredato in stile country chic e dotato di tutti i comfort.Ospita 4 persone.Ventilatori nelle camer The apartment is located in the historic center right in front of the wonderful church of San Francesco and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can host up to 4 people. Fan in the rooms.

4.96 out of 5 average rating, 165 reviews

Guest house in Macciano

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.

4.91 out of 5 average rating, 211 reviews

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

4.92 out of 5 average rating, 65 reviews

Modern apartment in the heart of Tuscany

A few steps from Castiglion Fiorentino train station. Ideal for exploring not only this charming medieval city but also other beautiful Tuscan cities, such as Arezzo, Cortona and Siena. The apartment has 1 bathroom and 5 beds, ideal for families or groups of friends. There is also an additional sofa bed for extra guests. It also has a small loggia for relaxing. Its central location allows you to easily find services such as shops, restaurants and bars nearby.

4.98 out of 5 average rating, 133 reviews

Home in Prato

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.

4.99 out of 5 average rating, 123 reviews

Guest house in Perugia

Ethical house in Umbria

It is a 60 sqm annex suitable for couples who want to visit our region. We don't have a swimming pool but we have the truffle ground, the stream, the roe deer, porcupines, wild boars, our cats and the little dog Moti. In the garden, you will find herbs, fruit, and garden produce. Inside the cottage we rent, you will have our olive oil and helichrysum liqueur that we produce. We also produce saffron, but we sell it! Of course, pets are welcome!

Farm stay in San Fatucchio

4.92 out of 5 average rating, 213 reviews

1 room apartments in farmhouse whit pool

At Borgo Solario we have 4 apartments of this type, with 1 bedroom. Those 4 apartments are on ground floor, in rustic tuscany style living room with furnished kitchenet, 1 bedroom, bathroom with shower and private and independent entry. The property has a 360° view over the valley and down to the Trasimeno lake. Garden with common pool in summer and play ground. MAX people 2, no kids under 12 years old.

4.94 out of 5 average rating, 202 reviews

Home in Cortona

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!

4.98 out of 5 average rating, 66 reviews

Tuscany Villa Mammi

Grande Villa interamente in pietra,inserita all'interno di un bosco sulle colline di Castiglion Fiorentino;vicina alle località di Cortona,Arezzo e Siena. Di recente ristrutturazione gode di uno splendido panorama sulla Valdichiana godibile dalla confortevole terrazza a bordo piscina. All'interno del parco verde anche una vasca idromassaggio all'aperto con panorama mozzafiato.

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Popular amenities for Castiglion Fiorentino holiday rentals

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Pool

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Other great holiday rentals in Castiglion Fiorentino

Cottage in Castiglion Fiorentino

4.96 out of 5 average rating, 28 reviews

Charming Cottage with Pool

YaoRating, 5 stars3 weeks ago

We stayed a week at the cottage and had a wonderful time. The surroundings were so beautiful. There are quite a few beautiful towns nearby, perfect for day trips, but you’ll need a car, even to go to Castiglion Fiorentino, the nearest village. Fausto and Flavia were very welcoming and checked in us several times. The cottage was very clean and had everything we needed during our stay.

5 out of 5 average rating, 10 reviews

COPPA DI SOPRA Beautiful villa with superb view

TuckerRating, 5 stars7 months ago

The villa was in a beautiful location with picture perfect views of towns below. The house was very clean and well stocked. Would highly recommend to any looking for tranquil stay in the tuscan hillside.

4.83 out of 5 average rating, 18 reviews

Suite Apartment ~ B&B Palazzo Robicci

SusanRating, 5 stars5 days ago

I just can’t say enough about how much we enjoyed our stay at Francesca’s. The massive and ancient masonry walls and window openings make for a magical atmosphere - and consistent indoor temperature. The garden and views are absolutely wonderful. There’s a fabulous restaurant on the same square and many great coffee shops nearby. And Francesca is delightful and knowledgeable. I highly recommend visiting Castiglion Fiorentino, and staying in this marvelous AirBnB!!

5 out of 5 average rating, 5 reviews

casa Sonia

SilviaRating, 5 stars1 month ago

Perfect house, clean, quiet, and equipped with everything you need

4.54 out of 5 average rating, 26 reviews

three-room wallbox included

MassimilianoRating, 5 stars6 days ago

Great accommodation at a really affordable price. Spacious, clean rooms, well-equipped kitchen, clean, comfortable, new bathroom, well-cleaned sanitary facilities. It was a pleasant experience at Daniel's, and when I return to Castiglion Fiorentino, I will definitely return.

Apartment in Figline Valdarno

4.87 out of 5 average rating, 54 reviews

Agriturismo Casavecchia, l'Olivo

AnthonyRating, 5 stars3 weeks ago

We absolutely loved our stay and it exceeded our expectations. The staff were friendly and very helpful, the food was delicious and the apartment was a great size with all the amenities we needed. It was family friendly and our children loved the pool. It’s a beautiful location and very relaxing. We would love to come again. Thank you for making our holiday so lovely.