Holiday rentals in Castiglion Fiorentino

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Top-rated holiday rentals in Castiglion Fiorentino

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Guest favourite

Farm stay in Ruscello

4.99 out of 5 average rating, 320 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)

13–20 Oct

$214 SGD per night

Guest favourite

Flat 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 owned by the Camaldolesi villages in the 12th century. A few meters away are 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 private setting. Strategic point to visit Siena, Pienza, Anghiari, Arezzo, Cortona.....

10–17 Sep

$158 SGD per night

Guest favourite

Flat in Cortona

4.99 out of 5 average rating, 114 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.

30 Oct – 6 Nov

$182 SGD per night

Guest favourite

Villa in Castiglion Fiorentino

4.93 out of 5 average rating, 180 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

8–15 Feb

$532 SGD per night

Guest favourite

Cottage in Geggiano

4.99 out of 5 average rating, 108 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.

1–8 Nov

$899 SGD per night

Guest favourite

Apartment 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.

19–26 Nov

$106 SGD per night

Guest favourite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 310 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

30 Nov – 7 Dec

$216 SGD per night

Guest favourite

Cottage in Montagnano

4.93 out of 5 average rating, 116 reviews

Charming cottage in Tuscany

Charming cottage situated on a hill with 360-degree views. Oasis of peace and tranquility. Surrounded by greenery. Large swimming pool Barbecue area Inside, a room with a French bed, a living room with a sofa bed, a bathroom, a kitchenette and an indoor and outdoor dining area. Ideal for couples and families with one or two children .

29 Jan – 5 Feb

$166 SGD per night

Guest favourite

Flat in Ville di Corsano

4.97 out of 5 average rating, 201 reviews

"Red Rose" apartment with a view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, with panoramic views of Siena. Located at the Villas of 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..).

14–21 Mar

$179 SGD per night

Guest favourite

Home in Monticchiello

4.97 out of 5 average rating, 134 reviews

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

23–30 Jul

$435 SGD 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

19–26 Mar

$1,128 SGD per night

Superhost

Home in Castiglion Fiorentino

4.85 out of 5 average rating, 41 reviews

Gorgeous, light studio in Tuscan hilltown

Come & discover this beautiful studio apartment inside the historical centre of a charming tuscan hill town. Lovingly restored, the 14th century building has been transformed into a gorgeous self-contained space with modern fixtures and appliances.

3–10 Jul

$67 SGD per night