Vacation rentals in Castiglion Fiorentino

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Top-rated vacation rentals in Castiglion Fiorentino

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Guest favourite

Farm stay in Ruscello

4.99 out of 5 average rating, 318 reviews

Agriturismo Fattoria La Parita

Provençal-style apartment nestled between the 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. It includes a basic Italian breakfast (coffee, tea, milk, cookies, etc.) that you can prepare on your own, if you want to try one of the famous breakfasts prepared and served by Sandra, the cost is €10 per person (6€ 5 to 15 years)

Dec. 14 – 21

$204 CAD per night

Guest favourite

Apartment in Castiglion Fiorentino

5.0 out of 5 average rating, 38 reviews

"Borgo Sant'Andrea al Pozzo" in Ancient Abbey

Completely renovated residence inside an ancient Abbey, already mentioned in 1114 AD and property of the Camaldolese friars in the twelfth century. A few meters from the historic walls of Castiglion Fiorentino dating back to 1200 AD and Porta Romana. It is 500 meters walk from the historic center of Castiglion Fiorentino and 15 minutes by car from Cortona. A unique stay, between history and nature, in a relaxing and reserved context. Strategic point to visit Siena, Pienza, Anghiari, Arezzo, Cortona.....

Sep. 10 – 17

$165 CAD per night

Guest favourite

Home in Castiglion Fiorentino

4.98 out of 5 average rating, 55 reviews

The little turret

The proposed farmhouse is a typical terrace made of characteristic Tuscan stone, ideal for those who want to spend relaxing holidays immersed in the green of the Castilian hills surrounding the small Chio valley. The accommodation, with turret, is arranged on three levels: the portion of the building that can be used is located on the first floor with living/dining room and equipped kitchen and on the second floor with double bedroom, double bedroom and bathroom with shower, all furnished in style.

Dec. 1 – 8

$112 CAD per night

Guest favourite

Apartment in Cortona

4.99 out of 5 average rating, 112 reviews

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.

Jan. 22 – 29

$181 CAD per night

Guest favourite

Villa in Castiglion Fiorentino

4.93 out of 5 average rating, 179 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

Feb. 8 – 15

$581 CAD per night

Guest favourite

Cottage in Geggiano

4.99 out of 5 average rating, 107 reviews

Villa di Geggiano - Guesthouse

The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR.

Nov. 25 – Dec. 2

$699 CAD per night

Guest favourite

Apartment in Castiglion Fiorentino

4.86 out of 5 average rating, 7 reviews

Casa il Cassero, rustic-style apartment free WI-FI

Appartamento in un antico palazzo, ristrutturato mantenendo inalterati gli antichi materiali. Un design lineare che ben si abbina alla presenza di travi in legno e pavimento in cotto antico. Casa il Cassero is a rustic-style apartment situated in the heart of the ancient village of Castiglion Fiorentino, built in the 17th century. It was recently renovated, by keeping the ancient materials unchanged, with a modern design that perfectly matches wooden beams and terracotta flooring.

Aug. 2 – 9

$100 CAD per night

Guest favourite

Apartment in Castiglion Fiorentino

4.91 out of 5 average rating, 22 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.

Aug. 27 – Sep. 3

$139 CAD per night

Guest favourite

Condo in Castiglion Fiorentino

4.95 out of 5 average rating, 62 reviews

[Castiglion Fiorentino] Gem under the tower

Cozy flat of nearly located in the heart of Castiglion Fiorentino, right under the Cassero tower, just a short stroll from the main shops, cafès and restaurants of Corso Italia. Modern, sunny and quiet flat on the first floor of a block of flats without lift. It is equipped with air conditioning , a 42 inch TV , free wi-fi connection. Ideal for its tranquillity and silence, it is particularly recommended for couples and families with babies.

Oct. 31 – Nov. 7

$117 CAD per night

Guest favourite

Cottage in Montagnano

4.93 out of 5 average rating, 116 reviews

Charming cottage in Tuscany

Charming cottage located on a hill overlooking 360 degrees. Oasis of peace and quiet. Surrounded by greenery. Large swimming pool BBQ area Inside the room with French bed, living room with sofa bed, bathroom, kitchenette and indoor and outdoor dining space. Ideal for couples and families with one/two children. Cot available

Oct. 31 – Nov. 7

$175 CAD per night

Guest favourite

Apartment in Ville di Corsano

4.97 out of 5 average rating, 200 reviews

"Red Rose" apartment with a view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, with a panoramic view of Siena. Located in the Villas di Corsano, just 14 km from the city. Ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d 'Orcia, Crete Senesi...).

Jan. 4 – 11

$209 CAD per night

Guest favourite

Villa in Ambra

4.98 out of 5 average rating, 107 reviews

Chianti Villa in Tuscany near Siena & Arezzo

Villa with 5bedrooms and 10sleeps in Chianti . Land of wine, good food and old traditions. Distances from the villa to:Siena 25km,Arezzo 35km,Florence 60km,villa with swimming pool obtained from the careful restoration of an ancient stone farmhouse

Nov. 10 – 17

$1,237 CAD per night