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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 $51 SGD 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.

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Guest favourite
Home in Castiglion Fiorentino
5.0 out of 5 average rating, 12 reviews

Il Giardino sotto la Torre

Il Giardino sotto la Torre è situato a Castiglion Fiorentino, dentro le mura del centro storico, a circa 20 minuti da Arezzo , un’ora da Firenze, Siena e Perugia ed è vicino alla stazione ferroviaria. Ci sono tre camere matrimoniali e un divano letto, due bagni entrambi con doccia, wc, bidet, lavandino e asciugacapelli. Asciugamani, telo doccia e lenzuola sono forniti gratuitamente. È presente un giardino, lastricato e privato, dove è possibile consumare i pasti e rilassarsi durante la giornata.

LocationFamilyAccuracy

Guest favourite
A living area features a comfortable gray sofa accompanied by a bright decorative cushion. Light wood flooring complements the simple dining table and chairs. The walls are adorned with framed artwork and mirrors, providing a welcoming ambience.
Flat in Castiglion Fiorentino
4.93 out of 5 average rating, 14 reviews

casa Sonia

Casa Sonia è un delizioso attico al 4* piano, dotato di ascensore. Si trova in una zona tranquilla a 2 passi dal centro storico di Castiglion Fiorentino, a 15 min dall’Equestrian Centre e da Arezzo e a 15 min da Cortona. Vicinissimo alla stazione ferroviaria. Casa Sonia dispone di una camera matrimoniale, una cameretta e un divano letto. La cucina è dotata di tutti i confort (lavatrice, lavastoviglie, frigorifero, forno e macchina caffè espresso) L’appartamento è dotato di aria condizionata.

LocationHospitalityHeating

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, 241 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

FamilyLocationBack garden

Top guest favourite
Villa in Cortona
4.81 out of 5 average rating, 109 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

FamilyLocationGrill

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 in Castiglion Fiorentino
4.99 out of 5 average rating, 90 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.

LocationFamilyWalkability

Top guest favourite
An infinity pool is framed by stone decking and wooden lounge chairs, inviting relaxation. Umbrellas provide shade, while terraced gardens with olive trees rise in the background. The surrounding landscape features gently rolling hills and clear blue skies, enhancing the serene outdoor setting.
Villa in Cortona
5.0 out of 5 average rating, 96 reviews

Stunning Tuscan Villa & Panoramic Infinity Pool

Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

LocationValueCondition

Top guest favourite
Villa in Castiglion Fiorentino
5.0 out of 5 average rating, 25 reviews

Beautiful and cozy country-house, sleeps 11

Exquisite two-storey villa with open-plan living and dining areas and five bedrooms overlooking the pool and countryside. Ideal for families or friends, with generous indoor and outdoor spaces. A private courtyard opens onto a beautiful pool and two dining areas set among olive trees. The main building features a private spa with chromotherapy shower and infrared sauna with red light. Pool heating available on request. Designed for relaxation, wellness and shared moments.

FamilyLocationKitchen

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 in Castiglion Fiorentino
5.0 out of 5 average rating, 40 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.

LocationFamilyBiking

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 in Castiglion Fiorentino
4.93 out of 5 average rating, 108 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.

ValueFamilyIndoor spaces

Guest favourite
The traditional stone house is surrounded by a well-maintained lawn, showcasing a multi-level structure with a picturesque roofline. Large arched windows accentuate the façade, providing ample natural light. A clear blue sky serves as a backdrop, highlighting the tranquil rural setting.
Villa in Castiglion Fiorentino
4.95 out of 5 average rating, 19 reviews

Podere Ortaglia di Sotto

Located in the Tuscan countryside, a 10-minute drive from Castiglion Fiorentino, Podere Ortaglia di Sotto offers a private pool with enclosed garden, WiFi and free private parking. The holiday home features 5 bedrooms, 6 bathrooms, a flat-screen TV, a dining area, a fully equipped kitchen and a terrace with mountain and valley views.(The pool is available from the last week of May to the second week of October .The dates may vary depending on the weather.)

FamilyLocationBack garden

Top guest favourite
Villa in Arezzo
4.99 out of 5 average rating, 122 reviews

Tuscany View - Villa Arianna

This beautiful villa, which can accommodate up to ten (10) people, will provide an unparalleled Tuscan experience.  While positioned perfectly to allow easy access to the most beautiful towns and villages of southern/central Tuscany (such as Arezzo, Florence, Siena, Cortona, Montepulciano) and northern Umbria (such as Perugia, Orvieto, Assisi); you’ll find this villa offers complete privacy as well as a sense of peace and tranquility to all who visit.

ValueLocationView

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.
Flat in Castiglion Fiorentino
4.96 out of 5 average rating, 25 reviews

Casa La Girandola - Viaggio nei vicoli medievali

Casa la Girandola si trova in centro a Castiglion Fiorentino, in un palazzo storico appena ristrutturato a pochi passi dalle vie principali del paese. Ogni stanza è caratterizzata da un arredamento ricercato e accogliente, con soffitti a volta o travi a vista e dettagli degli antichi affreschi riportati alla luce durante la ristrutturazione. Le ampie finestre offrono splendidi scorci sia sui tetti del centro storico che sul verde della Valdichiana.

LocationFamilyGetting around

Popular amenities for Castiglion Fiorentino holiday rentals

When is the best time to visit Castiglion Fiorentino?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$137 SGD$124 SGD$126 SGD$138 SGD$144 SGD$147 SGD$165 SGD$137 SGD$146 SGD$177 SGD$144 SGD$138 SGD
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.