
Holiday rentals in Castiglion Fiorentino
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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.

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.
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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

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
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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
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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

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.
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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.
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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

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

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

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.
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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
Stay near Castiglion Fiorentino's top sights
Other great holiday rentals in Castiglion Fiorentino

Villa il Laghetto with Infinity Pool in Tuscany
ValueFamilyLaundry

Casa Napoleone - Tuscan Villa w/ pool near Cortona
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La vita è bella
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Charming Cottage with Pool
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Casa Bianchini | Duplex 6-bedroom apartment (12 +1
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-Le Mura Luxury Room- ROOM & PERSONAL SPA
LocationFamilyAir conditioning

Casa il Cassero, rustic-style apartment free WI-FI
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Coaching House
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When is the best time to visit Castiglion Fiorentino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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. 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
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.
Destinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Mercato Centrale
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Del Chianti
- Palazzo Vecchio
- Piazza della Signoria
- Basilica of St Francis
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Centro Storico Orvieto
- Stadio Artemio Franchi
- Basilica of Santa Croce





