Some info is shown in its original language. Translate

Holiday rentals in Castiglion Fiorentino

Find and book unique accommodation on Airbnb

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 £30 per night before taxes and fees

  • Verified guest reviews

    Over 1,920 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 60 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

    90 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!

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
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.
Apartment
4.97 out of 5 average rating, 75 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
The exterior of a charming stone villa is surrounded by a lush garden featuring vibrant lavender plants. Stairs lead to a welcoming entrance adorned with potted flowers and a shaded seating area. The rustic façade reflects traditional Tuscan architecture against a clear blue sky.
Villa
4.97 out of 5 average rating, 126 reviews

Charming Tuscan Villa with View forFamily&Friends

Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Guest favourite
Home
4.96 out of 5 average rating, 134 reviews

Palazzo Monaci - Piscina nelle crete Senesi

Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

Top guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage
4.99 out of 5 average rating, 153 reviews

Villa di Geggiano - Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

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.
Guest house
4.97 out of 5 average rating, 234 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.

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
4.99 out of 5 average rating, 513 reviews

Agriturismo Fattoria La Parita

Appartamento in stile provenzale immerso tra il vigneto e gli olivi. Godrete della tranquillità della campagna a 10 km dalla città e 4 dall'autostrada. Il canto di ghiandaie e cucù faranno da colonna sonora al soggiorno mentre i caprioli brucano tra gli olivi. E' inclusa una colazione base all'italiana (caffè, tè, latte, biscotti ecc.), se invece preferite una colazione più ricca e servita al tavolo il costo è 15€ a persona (10€ da 5 a 15 anni, gratis meno di 5 anni). Disponibile wallbox EV.

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
4.9 out of 5 average rating, 239 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

Guest favourite
Villa
4.8 out of 5 average rating, 104 reviews

Tuscan Villa Luigina with Pool & Panoramic View

If you want to live in a postcard .... Villa Luigina is the ideal place, all the rooms have a panoramic view, a dining room with a view ... a breakfast room with a view, or you can eat outside in the garden in front of the house and enjoy the spectacular view of the old town!! In the fascinating Tuscan hills, among olive trees and vineyards, a stone villa in perfect harmony with the environment in a strategic position to discover the secrets of Tuscany and Umbria. CIN:IT051012C2129WHTZX

Top guest favourite
A private pool area is surrounded by lush greenery and offers stunning views of the landscape below. Several sun loungers are positioned on the pool deck, with large umbrellas providing shade. The serene ambiance invites relaxation amid nature.
Villa
4.99 out of 5 average rating, 85 reviews

Tuscany Villa Mammi

Grande villa in pietra ristrutturata tra i boschi di Castiglion Fiorentino, vicono a Cortona, Arezzo e Siena. Un paradiso di privacy con piscina, idromassaggio panoramico con vista mozzafiato sulla valle e ping pong. Godetevi serate magiche sotto le stelle grazie all'autentico barbecue in pietra e al forno a legna per la pizza. Il rifugio ideale per chi cerca relax, natura e comfort nel cuore della Toscana, perfetto per famiglie o gruppi che sognano una vacanza davvero indimenticabile.

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.
Flat
5 out of 5 average rating, 34 reviews

Pendici 15, piccolo appartamento

Accogliente appartamento all’interno di un casolare in pietra dove godere dell’atmosfera della campagna toscana ed allo stesso tempo della vicinanza al centro storico di Castiglion Fiorentino. Ideale per coppie, famiglie e viaggiatori con amici a quattro zampe, è il punto di partenza ideale per visitare la Toscana. L’alloggio coniuga il fascino rustico delle case in pietra con i comfort moderni, offrendo un soggiorno rilassante in un contesto silenzioso e panoramico.

Guest favourite
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.
Flat
4.92 out of 5 average rating, 101 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
Flat
5 out of 5 average rating, 36 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£81£74£74£86£93£90£98£81£86£104£85£82
Avg. temp5°C6°C9°C12°C16°C21°C23°C24°C19°C14°C9°C5°C

Frequently Asked Questions

  • What are the best places to stay in Castiglion Fiorentino?

    Stays near the town center provide easy access to cafés, markets, and historic sites. Countryside villas and renovated farmhouses are frequently suggested for those wanting extra privacy and scenic views.

  • What are the best things to do in Castiglion Fiorentino with kids?

    Children can join creative workshops, enjoy playgrounds, and participate in seasonal town festivals. Interactive museum exhibits and countryside walks are often recommended for families.

  • What are some of the best things to do in Castiglion Fiorentino?

    Explore the historic old town, visit hillside churches, and take in local art at galleries. Walking through medieval streets and enjoying Tuscan cuisine are frequently suggested activities.

  • How is the weather in Castiglion Fiorentino?

    Castiglion Fiorentino has cool, rainy winters around 33–49°F (0–9°C), and warm, dry summers near 82–89°F (28–32°C). Spring and autumn bring milder temperatures and changing foliage.

  • When is the best time to visit Castiglion Fiorentino?

    Late spring and early autumn are frequently suggested for milder temperatures near 66–74°F (19–23°C) and cultural events. The town’s landscape is especially lively during festival seasons.

  • What are the best places to visit in Castiglion Fiorentino?

    Explore the old town center, climb to historic towers, and visit local churches. The area has traditional markets, artisan workshops, and an archaeological museum.

  • What are some hiking trails in Castiglion Fiorentino?

    The area has countryside trails that lead through olive groves, woodland paths, and scenic hilltops. Walks frequently include historical ruins and views of the surrounding valley.

  • What are some family activities we can do in Castiglion Fiorentino?

    Families often explore local parks, enjoy hands-on workshops in pottery, and attend community festivals. Visiting museums or taking part in guided nature walks around town are frequently suggested.

  • What are some of the best day trip ideas from Castiglion Fiorentino?

    Nearby hill towns known for Renaissance history, vineyards, and artisan shops are popular day trip choices. Exploring local farms or visiting larger cities with museums and galleries is often recommended.

  • Are there any pet friendly accommodations available in Castiglion Fiorentino?

    Castiglion Fiorentino has a selection of pet friendly vacation rentals. Many hosts welcome pets, especially in countryside areas and within town, making it easier to explore with your companion.

  • What are some local tips for visiting Castiglion Fiorentino?

    Locals often suggest starting mornings at a café, wearing comfortable shoes for cobbled streets, and visiting regional markets for fresh produce. Try learning a few Italian phrases to connect with residents.

  • What is Castiglion Fiorentino known for?

    Castiglion Fiorentino is known for medieval architecture, hillside panoramas, and vibrant cultural traditions. It also has historic churches and regional agricultural fairs.

  • What are the best hidden gems to explore in Castiglion Fiorentino?

    Explore small artisan shops along quieter streets, discover peaceful local gardens, and step into traditional workshops where crafts are still practiced. Around the historic center, family-run trattorias and local markets provide a glimpse into daily life.

  • What are the best foods to try in Castiglion Fiorentino?

    Castiglion Fiorentino has locally rooted Tuscan fare, such as handmade pasta, hearty ribollita soup, and pecorino cheese. Olive oil from nearby groves and rustic breads are frequently suggested additions.

  • What should I bring for a trip to Castiglion Fiorentino?

    Bring comfortable walking shoes, layers for changing temperatures, and a travel adapter. A light jacket for evenings and sunscreen during warmer months come in handy.

  • What is the nightlife in Castiglion Fiorentino like?

    Castiglion Fiorentino has a relaxed evening scene, with local wine bars, cafés, and occasional live music. Social gatherings in historic squares are common, especially during festivals.

  • What are the most popular events or festivals in Castiglion Fiorentino?

    Castiglion Fiorentino hosts medieval reenactments in late spring, a historic Palio festival, and seasonal fairs celebrating local food and crafts. Community gatherings and music events are often popular throughout the year.

  • Are there family friendly vacation rentals in Castiglion Fiorentino?

    Castiglion Fiorentino has a variety of family friendly accommodations, including larger apartments and countryside homes with outdoor space. Hosts often share tips for nearby family activities and local dining.

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