
Holiday rentals in Castiglion Fiorentino
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Top-rated holiday rentals in Castiglion Fiorentino
Guests agree: these stays are highly rated for location, cleanliness and more.

Farmhouse Fattoria La Parita
Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

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.

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.

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

Your Tuscan oak tree house, enchanting Val d'Orcia
The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

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 farmhouse 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 to visit Tuscany. The accommodation combines the rustic charm of stone houses with modern comforts, offering a relaxing stay in a quiet and panoramic setting.

Cortona Shabby Chic House - independent & balcony-
Questo è un appartamento curato da una Superhost che vive Cortona ogni giorno. Il mio alloggio è situato in pieno centro storico a soli pochi passi dalle piazze e vie principali. Questo grazioso appartamento è di recente ristrutturazione e può ospitare fino a 3 persone. Appartamento indipendente con entrata singola tutto in un solo piano, con balcone. Arredato con cura, dotato di tutti i comfort per un totale relax

Esplora la natura al centro di Vigneti Chianti
Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.

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.

Casale Santa Barbara - Exclusive Apartment
Your private Tuscan retreat between Pienza and Montepulciano. A spacious 100 m² apartment for two, with exclusive access, a large private garden and breathtaking views over the Val d’Orcia hills. Elegance, calm and authenticity — just you… and Tuscany.
Popular amenities for Castiglion Fiorentino holiday rentals
Other great holiday rentals in Castiglion Fiorentino

Affitti Brevi Siena - The heart of Tuscany

Charming Cottage with Pool

Fantastic Apartment in the Heart of Toscana

Romantic Tuscan Holiday House

Exceptional view of the valley in the center

The walnut tree view, Montepulciano

Cipressini 2 - piscina e vista mozzafiato

Sorbino's Nest by Interhome
When is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £69 | £63 | £67 | £86 | £92 | £90 | £97 | £81 | £86 | £104 | £84 | £81 |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Castiglion Fiorentino?
Yes! Work meets play with ease at over 30 vacation rentals in Castiglion Fiorentino featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Castiglion Fiorentino?
Four-legged friends are welcome in Castiglion Fiorentino. Choose from more than 50 vacation rentals for guests traveling with pets.
Are there Castiglion Fiorentino vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Castiglion Fiorentino, available on Airbnb. Make a splash and soak up the sun in style!
What types of vacation rentals are available in Castiglion Fiorentino?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Castiglion Fiorentino. From over 40 apartment rentals, over 10 house rentals to over 10 villa rentals, we've got you covered.
How much does it cost to stay in villa rentals in Castiglion Fiorentino?
Experience the best of Castiglion Fiorentino with our villa rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Castiglion Fiorentino?
Castiglion Fiorentino has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Castiglion Fiorentino have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Castiglion Fiorentino. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Castiglion Fiorentino have a kitchen?
Absolutely! We offer over 10 condo rentals with a kitchen in Castiglion Fiorentino. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Castiglion Fiorentino have wifi?
Absolutely! We offer over 10 condo rentals with wifi in Castiglion Fiorentino. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Castiglion Fiorentino have free parking?
Absolutely! We offer over 10 house rentals with free parking in Castiglion Fiorentino. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Castiglion Fiorentino

Total holiday rentals
Explore 90 holiday rentals in Castiglion Fiorentino

Nightly prices starting at
Castiglion Fiorentino holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 1,740 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
80 of Castiglion Fiorentino holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Castiglion Fiorentino rentals

4.8 Average rating
Castiglion Fiorentino stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Rentals with a patio Castiglion Fiorentino
- Rentals with outdoor seating Castiglion Fiorentino
- Rentals with a fireplace Castiglion Fiorentino
- Family-friendly rentals Castiglion Fiorentino
- House rentals Castiglion Fiorentino
- Rentals with pools Castiglion Fiorentino
- Flat rentals Castiglion Fiorentino
- Pet-friendly rentals Castiglion Fiorentino
- Rentals with a washing machine and dryer Castiglion Fiorentino
- Villa rentals Castiglion Fiorentino
- Smoking-friendly rentals Castiglion Fiorentino
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Strozzi Palace
- Mercato Centrale
- Santa Maria Novella
- Ponte Vecchio
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Del Chianti
- Basilica of Santa Maria Novella
- Eremo Di Camaldoli
- Piazza della Signoria
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazzale Michelangelo
- Piazza della Repubblica
- Parco delle Cascine
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Stadio Artemio Franchi
- Avignonesi Winery Fattoria Le Capezzine




