
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.

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

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

Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

Luxurious Medieval Tower & Private Concierge
It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Italian Internal
Knock on the door of this house, and an inspiring world will open up to you. The modern design, now luxurious, now fun, blends beautifully with the structures and airiness of the 18th-century rural complex, and offers a breathtaking panoramic window. The house is located within a residence, and use of the pool is shared with other guests in the complex. Surrounded by green hills, offers an ideal accommodation for families looking for a relaxing stay. The house is ideal for four people.

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.

La casina sulle Mura with garden
La Casina è situata nella parte alta di Cortona, nella zona denominata "il Poggio". Si puo' giungere in auto fino al suo ingresso. Il Centro citta' e' raggiungibile a piedi in pochi minuti, percorrendo strade e vicoli caratteristici. Gode di una splendida vista su Cortona e la Valdichiana. E' facile parcheggiare nelle vicinanze. Gli ospiti che giungono in treno in una delle stazioni vicine, su richiesta, possono essere prelevati e accompagnati a destinazione.

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.

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!

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.

Poggio Bicchieri Holiday Farm - Poesia apartment
Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.

Civetta golosa, Charming two-room apartment in the historic center
Cozy and practical two-room apartment on the second floor of a historic building, with an independent entrance and recently renovated. It is equipped with everything even for long stays. It has a comfortable double bedroom, bathroom and kitchen space. View of the city. Just 150 meters from the free parking lot in Piazzale del Mercato.
Popular amenities for Castiglion Fiorentino holiday rentals
Other great holiday rentals in Castiglion Fiorentino

Charming Cottage with Pool

Il Sasso Apartment

Charming Apartment with Small Gardens, Pool Access

-Le Mura Luxury Room- ROOM & PERSONAL SPA

Beautiful view on the valley

Wine Loft in the vineyards

Villa Medici Donnini Superior Apartment

Rural Tuscany | Family farmstay with restaurant
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 | £85 | £92 | £89 | £96 | £80 | £85 | £103 | £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.
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 30 apartment rentals to over 10 house rentals, we've got you covered.
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!
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.
How much does it cost to stay in condo rentals in Castiglion Fiorentino?
Experience the best of Castiglion Fiorentino with our condo rentals, starting at about $60 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 a kitchen?
Absolutely! We offer over 30 apartment rentals with a kitchen 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.
Do house rentals in Castiglion Fiorentino have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Castiglion Fiorentino. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Castiglion Fiorentino have wifi?
Absolutely! We offer over 30 apartment rentals with wifi 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
- Pet-friendly rentals Castiglion Fiorentino
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- Rentals with pools Castiglion Fiorentino
- Rentals with a patio Castiglion Fiorentino
- Rentals with a fireplace Castiglion Fiorentino
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- Rentals with outdoor seating Castiglion Fiorentino
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Mercato Centrale
- Strozzi Palace
- Ponte Vecchio
- Santa Maria Novella
- 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
- Pitti Palace
- Parco delle Cascine
- Boboli's Garden
- Palazzo Vecchio
- Stadio Artemio Franchi
- Medici Chapel




