Vacation rentals in Castiglion Fiorentino

4.99 out of 5 average rating, 422 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

Apartment 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

Guesthouse 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, 212 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

4.98 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, 275 reviews

Apartment in Sinalunga

Resort Panoramic view - Free parking

Appartamento nuovo , potente Wi-Fi, SMART TV, bagno privato , Aria Condizionata, cucina privata , lavanderia , parcheggio privato gratuito . Sala da tea ad uso gratuito . Vista panoramica mozzafiato . Tra le Crete Senesi e la Val D’Orcia , a 800metri dal centro del paese , con ristoranti , bar e supermercati . Posto strategico per visitare le principali località in Toscana : Montalcino , Pienza , Siena , Arezzo , Rapolano Terme , Montepulciano .

5 out of 5 average rating, 16 reviews

Casa La Girandola – Journey through the medieval alleys

Casa la Girandola is located in the center of Castiglion Fiorentino, in a newly renovated historic building just a few steps from the town's main streets. Each room is characterized by refined and welcoming furnishings, with vaulted ceilings or exposed beams and details of the ancient frescoes brought to light during the renovation. The large windows offer splendid views of both the rooftops of the historic center and the green of the Valdichiana.

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.

4.98 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.

4.89 out of 5 average rating, 198 reviews

Farm stay in Simignano

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

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Pool

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Other great vacation rentals in Castiglion Fiorentino

Cottage in Castiglion Fiorentino

4.96 out of 5 average rating, 28 reviews

Charming Cottage with Pool

YaoRating, 5 stars1 month 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 stars8 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.

Condo in Castiglion Fiorentino

4.69 out of 5 average rating, 13 reviews

Delightful "I Quattro Cantoni" Apartment

KaylaRating, 5 stars4 days ago

enrico and his place were perfect! location was amazing and he was so helpful! will definitely stay again 10/10

4.83 out of 5 average rating, 18 reviews

Suite Apartment ~ B&B Palazzo Robicci

SusanRating, 5 stars1 week 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!!

4.88 out of 5 average rating, 33 reviews

[Residenza Colle Secco] Country villa

DarioRating, 5 stars2 months ago

Magnificent place, on the hills of Castiglion Fiorentino a few km from the center, super hospitality, the house is splendid, everything well-kept and in its place, fully equipped kitchen, very comfortable beds, very clean bathroom and large shower. Relaxation area and large, comfortable sofas :-) all with wooden beams... Very kind Michele and his family, in the welcome and service. I absolutely recommend a weekend in this paradise of beauty, tranquility, and relaxation :-) It deserves it!!!

5 out of 5 average rating, 6 reviews

casa Sonia

GiuliaRating, 5 stars3 days ago

Great apartment and well maintained. Emanuele and Sonia are very helpful and hospitable.