
Holiday rentals in Castiglion Fiorentino
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Top-rated holiday rentals in Castiglion Fiorentino
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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.

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.

Fontarcella, H&R- mediterranean home with jacuzzi
Situata nelle colline a cavallo tra Montepulciano,Castiglione del Lago e Cortona, Fontarcella si presenta come una villetta indipendente immersa nel verde, che offre jacuzzi e parcheggio privati; Scoprirete un luogo senza tempo, per condividere momenti preziosi. La struttura, arredata in stile mediterraneo, dispone di climatizzazione e wi-fi gratuita. Il giardino, interamente recintato, offre vari comfort. A pochi minuti dalle autostrade, Fontarcella è facilmente raggiungibile dai viaggiatori.

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

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.

The Tavern in the Hills
La Taverna is located in a gentle valley (a five-minute drive from the city of Arezzo) where the days are sweet and the surrounding countryside marks every moment of the day, a bike ride, a dip in the pool, a horseback ride in the nearby riding school and a little shopping and culture in the millennial city of Arezzo. In front of you, the hills will offer you an enchanting view, in the garden and in the pool you will spend moments of pure relaxation.

Rural Tuscany | Panoramic farmhouse with pool
Podere Il Belvedere is a charming estate located in Castiglion Fiorentino, just 15 minutes from Cortona. The property features seven well-equipped apartments, each with a living room and kitchenette. Guests can enjoy a pool area with gazebos and sunbeds, a barbecue area, and free parking. With its stunning views, proximity to Tuscany’s art cities, and activities like wine tastings or cooking classes, it’s perfect for a memorable holiday.

Villa Feronia – Heated Pool & Rooftop Escape
Welcome to Villa Feronia, a contemporary 3-bedroom retreat nestled in a 2-hectare olive grove near Passignano sul Trasimeno. Enjoy refined indoor-outdoor living with 3.5 bathrooms, high-speed Wi-Fi, a smart home system, an infinity saltwater heated pool, and a rooftop terrace with a fire pit. Eco-friendly and elegantly designed, it’s the ideal escape to relax, recharge, and experience authentic Italian beauty.

AGRITURISMO PODERE SCURCOLI TOWER
It consists, on the ground floor, of a kitchen-living room equipped with a sofa bed and a bathroom. A covered veranda allows you to eat and spend time outside enjoying the wide panorama and beautiful sunsets. On the first floor there is a double bedroom with a small balcony and a bathroom with shower. The house is served by an air conditioning system. Independent entrance. Square meters: 45. Sleeps: 3.

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.

Borgo Iesolana Country Retreat Family Suite Sup.
Charming Family Suite inside the Borgo Iesolana Estate, set in an enchanting, silent and unspoiled landscape and close to the cities of Siena, Arezzo and Florence. Situated on first floor with 2 bedrooms, 2 bathrooms, Living room, pool, parking, Airco, WiFi and TV. Tasty Restaurant in the property for breakfast, light lunch, aperitif and dinner. Breakfast included.
Popular amenities for Castiglion Fiorentino holiday rentals
Other great holiday rentals in Castiglion Fiorentino

Tuscany Villa Mammi

Boggina. Private villa with pool, walk to village

Family Forest - Pool in the Crete Senesi

Luxury Villa with Private Pool

Casa Monte

Agriturismo S. Angelo | Casa Uliveti

casa Sonia

Panoramic View & Balcony · Charming Apartment ·A/C
When is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $118 SGD | $108 SGD | $115 SGD | $146 SGD | $158 SGD | $153 SGD | $166 SGD | $138 SGD | $146 SGD | $177 SGD | $144 SGD | $139 SGD |
| 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 10 house rentals, over 40 apartment rentals to over 10 villa rentals, we've got you covered.
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 $70 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 villa rentals in Castiglion Fiorentino have air conditioning?
Absolutely! We offer over 10 villa rentals with air conditioning in Castiglion Fiorentino. Enjoy a tailored experience with all the comforts you desire.
Do villa rentals in Castiglion Fiorentino have a kitchen?
Absolutely! We offer over 10 villa rentals with a kitchen 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 40 apartment rentals with wifi in Castiglion Fiorentino. Enjoy a tailored experience with all the comforts you desire.
Do villa rentals in Castiglion Fiorentino have free parking?
Absolutely! We offer over 10 villa 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 $38 SGD 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 outdoor seating Castiglion Fiorentino
- Villa rentals Castiglion Fiorentino
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- Rentals with a washing machine and dryer Castiglion Fiorentino
- Flat rentals Castiglion Fiorentino
- Rentals with a patio Castiglion Fiorentino
- House rentals Castiglion Fiorentino
- Family-friendly rentals Castiglion Fiorentino
- Rentals with a fireplace Castiglion Fiorentino
- Pet-friendly rentals Castiglion Fiorentino
- Rentals with pools Castiglion Fiorentino
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Strozzi Palace
- Santa Maria Novella
- Ponte Vecchio
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Del Chianti
- Basilica of Santa Maria Novella
- Mercato Centrale
- Eremo Di Camaldoli
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazzale Michelangelo
- Pitti Palace
- Parco delle Cascine
- Palazzo Vecchio
- Boboli's Garden
- Stadio Artemio Franchi
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapel




