Some info has been automatically translated. Show original language

Holiday houses in Castiglion Fiorentino

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Castiglion Fiorentino

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Top Guest favourite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay in Ruscello
4.99 out of 5 average rating, 499 reviews

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.

Guest favourite
Condo in Castiglion Fiorentino
4.95 out of 5 average rating, 22 reviews

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.

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 132 reviews

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.

Top Guest favourite
The spacious sleeping area features a plush bed adorned with soft pillows and blankets in shades of pink and gray. A sleek, round hot tub is positioned nearby, accompanied by decorative candles and a mirrored fireplace, enhancing a tranquil atmosphere.
Condo in Castiglion Fiorentino
4.97 out of 5 average rating, 73 reviews

-Le Mura Luxury Room- ROOM & PERSONAL SPA

In pieno centro storico,all'interno di un edificio interamente ristrutturato e situato dentro le mura medievali,a pochi passi dai principali punti di interesse e di divertimento. Una nuova tipologia di pernottamento e benessere,dove regalarvi un momento di lussuoso relax. Ampia zona notte,sauna,vasca idromassaggio e doccia con cromoterapia,zona relax con tisaneria,bagno privato,tv lcd,frigobar,tostapane,spremiagrumi,macchina per il caffè..ad uso esclusivo ed illimitato per tutto il Vs soggiorno.

Top Guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 225 reviews

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.

Guest favourite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino
4.9 out of 5 average rating, 237 reviews

Tuscan charm of villa - countryside - Villa Senaia

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

Superhost
The living area features a spacious sectional sofa, a modern television on a low cabinet, and a round dining table surrounded by four chairs. A map artwork adorns the wall, complemented by shelf plants, enhancing the open feel of the apartment.
Apartment in Castiglion Fiorentino
4.92 out of 5 average rating, 98 reviews

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.

Top Guest favourite
A light-filled living space features a comfortable sofa and a dining table set for four. A large TV is mounted on a white cabinet, while a door leads to the bedroom area, which appears partially visible in the background. Wooden beams enhance the ceiling's charm.
Condo in Cortona
4.99 out of 5 average rating, 209 reviews

Chicca: Cortona's historic center

Bright, delightful and welcoming apartment located right in the heart of the historic center of Cortona with an unforgettable view: the town hall on one side and Lake Trasimeno and the Valdichiana on the other. The apartment has been recently renovated and consists of a living room with sofa bed, a small kitchen, a double bedroom and two bathrooms. The apartment has WiFi, heating and air conditioning, a washing machine, oven, microwave, hairdryer and flat iron.

Guest favourite
A spacious bedroom features a warm terracotta ceiling with herringbone patterns. Natural light streams in through a window, illuminating the wooden furniture, including a wardrobe and a small table. Air conditioning is also visible, ensuring a comfortable environment.
Apartment in Castiglion Fiorentino
4.96 out of 5 average rating, 24 reviews

Casa La Girandola – Journey through the medieval alleys

Casa la Girandola is located in the center of Castiglion Fiorentino, in a newly renovated historic building just a few steps from the town's main streets. Each room is characterized by refined and welcoming furnishings, with vaulted ceilings or exposed beams and details of the ancient frescoes brought to light during the renovation. The large windows offer splendid views of both the rooftops of the historic center and the green of the Valdichiana.

Top Guest favourite
An aerial view of a stone farmhouse is presented, surrounded by lush greenery. A private garden features various seating arrangements, including loungers and a dining area under a sunshade. A pathway leads to the entrance, emphasizing the rustic charm of the setting.
Apartment in Castiglion Fiorentino
5 out of 5 average rating, 30 reviews

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.

Top Guest favourite
Farm stay in Arezzo
4.97 out of 5 average rating, 255 reviews

Explore nature in the center of 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.

Top Guest favourite
Apartment in Castiglion Fiorentino
5 out of 5 average rating, 32 reviews

Happy Nest Tuscany Between Florence and Rome

We are Eurosian young couples, we love traveling, we have been to more than 20 countries! We speak Italian, English, Vietnamese, Chinese, Polish. We offer a modern and elegant accommodation to every traveling lover all around the world, to help you find a comfortable and home-feeling place in the heart of Tuscany!!! Have fun and enjoy your time in this beautiful landscape ^^

Popular amenities for Castiglion Fiorentino holiday rentals

When is the best time to visit Castiglion Fiorentino?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$185 NZD$168 NZD$170 NZD$197 NZD$213 NZD$206 NZD$223 NZD$185 NZD$197 NZD$239 NZD$194 NZD$187 NZD
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°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 villa rentals, over 40 apartment rentals to over 10 house rentals, we've got you covered.

  • How much does it cost to stay in house rentals in Castiglion Fiorentino?

    Experience the best of Castiglion Fiorentino with our house rentals, starting at about $50 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 50 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 apartment rentals in Castiglion Fiorentino have a kitchen?

    Absolutely! We offer over 40 apartment rentals with a kitchen 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 10 villa 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 $69 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,760 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 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, 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!

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Arezzo
  5. Castiglion Fiorentino