
Holiday houses 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 surrounded by 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. A basic Italian breakfast (coffee, tea, milk, biscuits, etc.) is included, but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 for 5 to 15 year-olds, free for children under 5). EV wallbox available.

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.

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.

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 for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt 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

Stuart White Tea Central Panoramic & Garden
Offering ample space, the apartment features two double bedrooms, two full bathrooms, and a living room with a kitchen. The bedroom balconies offer stunning views of the valley and natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. It has also access to a secluded, terraced backyard garden. It provides a comfortable retreat perfect for long term stays. A public parking is available nearby.

Casale Santa Barbara - Exclusive Apartment
At a glance: • Location: perfect entry door to the Val d’Orcia between Pienza (8,5 km) and Montepulciano (8,5 km). • Charming warm old stones Tuscan house – completely restored in 2016 • Big apartment (100m2), designed for 2 persons, completely independent, fully furnished, Tuscan style with modern equipment. • Exclusivity: we are living on the 1st floor; the ground floor is yours. You are our only guests. • Spacious private garden (+ 300m2) • Stunning view on the Tuscan hills.

Green – The meadows in Tuscany
Apartment consisting of 1 double bedroom, equipped kitchen, large living room and bathroom TV, BBQ, (we provide the washing machine from 9 a.m. to 8 p.m. which is in our laundry room for those who request it). We recommend the car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and wifi Strategic location for visiting Tuscany and Umbria.

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.

Montepulciano Centro Storico
Nice 60 sqm apartment located in the main street of the village. It is located on the second and last floor of a historic palace. The entrance is located on the main street of the town while the windows overlook the outside of the walls offering a breathtaking view. The apartment consists of: entrance, living room with double sofa bed, bedroom, kitchen, bathroom with roof window. It is equipped with microwave, large oven, dishwasher, washing machine and wi-fi.

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!
Popular amenities for Castiglion Fiorentino holiday rentals
Other great holiday rentals in Castiglion Fiorentino

Podere Pereti Nuovi-modern Tuscan Villa

Stunning Tuscan Villa & Panoramic Infinity Pool

Family Forest - Pool in the Crete Senesi

Il Sasso Apartment

Ortaglia di Sotto Farm

Casa Tòrta - comfort room

Agriturismo Via della Stella | Apartment Lecci

Villa il Laghetto with Infinity Pool in Tuscany
When is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $166 NZD | $152 NZD | $161 NZD | $206 NZD | $222 NZD | $215 NZD | $233 NZD | $193 NZD | $206 NZD | $175 NZD | $191 NZD | $195 NZD |
| 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 10 house rentals to over 30 apartment 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 villa rentals in Castiglion Fiorentino?
Experience the best of Castiglion Fiorentino with our villa rentals, starting at about $100 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 house rentals in Castiglion Fiorentino have a kitchen?
Absolutely! We offer over 10 house 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 villa rentals in Castiglion Fiorentino have wifi?
Absolutely! We offer over 20 villa 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 $54 NZD per night before taxes and fees

Verified guest reviews
Over 1,850 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
80 of Castiglion Fiorentino holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Pet-friendly rentals Castiglion Fiorentino
- Rentals with a washing machine and dryer Castiglion Fiorentino
- Villa rentals Castiglion Fiorentino
- House rentals Castiglion Fiorentino
- Rentals with a fireplace Castiglion Fiorentino
- Family-friendly rentals Castiglion Fiorentino
- Rentals with outdoor seating Castiglion Fiorentino
- Smoking-friendly rentals Castiglion Fiorentino
- Rentals with pools Castiglion Fiorentino
- Apartment rentals Castiglion Fiorentino
- Santa Maria Novella
- Piazzale Michelangelo
- Lake Trasimeno
- Duomo di Firenze
- Basilica of Santa Maria Novella
- Ponte Vecchio
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Uffizi Gallery
- Fortezza da Basso
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- The Boboli Gardens
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Tenuta Le Velette
- Palazzo Vecchio
- Basilica of St Francis
- Stadio Artemio Franchi
- Castiglion del Bosco Winery
- Basilica di Santa Croce
- Teatro Verdi




