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Holiday houses 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 $56 AUD 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 and kid-friendly amenities

  • Pet-friendly accommodation

    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

  • Wi-Fi availability

    90 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!

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

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.

5.0 out of 5 average rating, 12 reviews
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

-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.

4.97 out of 5 average rating, 75 reviews
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

Chicca: centro storico di Cortona

Luminoso, delizioso e accogliente appartamento situato proprio nel cuore del centro storico di Cortona con un panorama indimenticabile: il palazzo comunale da una parte ed il lago Trasimeno e la Valdichiana dall'altra. L'appartamento è stato recentemente ristrutturato ed è composto da una sala con divano letto, una piccola cucina, una camera matrimoniale e due bagni. Nell'appartamento è disponibile WiFi, riscaldamento ed aria condizionata, lavatrice, forno, microonde, asciugacapelli e piastra.

4.98 out of 5 average rating, 224 reviews
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.
Apartment in Castiglion Fiorentino

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.

4.93 out of 5 average rating, 15 reviews
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

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

4.9 out of 5 average rating, 240 reviews
Guest favourite
Villa in Cortona

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

4.8 out of 5 average rating, 110 reviews
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

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.

4.99 out of 5 average rating, 90 reviews
Superhost
A cozy master bedroom features a spacious bed draped with soft linens. Wooden beams stretch across the ceiling, while bedside tables with lamps provide soft illumination. The warm tones of the walls create a serene environment, with a glimpse of the living area visible in the background.
Apartment in Castiglion Fiorentino

Casa il Cassero, rustic-style apartment free WI-FI

Appartamento in un antico palazzo, ristrutturato mantenendo inalterati gli antichi materiali. Un design lineare che ben si abbina alla presenza di travi in legno e pavimento in cotto antico. Casa il Cassero is a rustic-style apartment situated in the heart of the ancient village of Castiglion Fiorentino, built in the 17th century. It was recently renovated, by keeping the ancient materials unchanged, with a modern design that perfectly matches wooden beams and terracotta flooring.

4.71 out of 5 average rating, 28 reviews
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

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.

5.0 out of 5 average rating, 96 reviews
Top Guest favourite
Villa in Castiglion Fiorentino

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.

5.0 out of 5 average rating, 25 reviews
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

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.

5.0 out of 5 average rating, 43 reviews
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.
Apartment in Castiglion Fiorentino

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.

4.93 out of 5 average rating, 109 reviews

Popular amenities for Castiglion Fiorentino holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Stay near Castiglion Fiorentino's top sights

Velvet Underground

12 locals recommend

Castiglion Fiorentino

7 locals recommend

Castello di Montecchio Vesponi

3 locals recommend

Other great holiday rentals in Castiglion Fiorentino

Top Guest favourite
Villa in Arezzo

Casa Napoleone - Tuscan Villa w/ pool near Cortona

4.96 out of 5 average rating, 28 reviews
Guest favourite
The property features a charming rustic stone house and a secondary building set against a backdrop of bright blue skies and scattered clouds. Lush green grass surrounds the structures, enhancing the natural beauty of this tranquil countryside setting.
Villa in Castiglion Fiorentino

Villa il Laghetto with Infinity Pool in Tuscany

4.96 out of 5 average rating, 56 reviews
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

Podere Ortaglia di Sotto

4.95 out of 5 average rating, 19 reviews
Top Guest favourite
The charming cottage is constructed with warm-toned brick, featuring a staircase leading to a small balcony. Lush greenery surrounds the building, while the well-maintained gravel pathway guides to the entrance, complemented by vibrant flower pots adding a touch of color.
Cottage in Castiglion Fiorentino

Charming Cottage with Pool

4.98 out of 5 average rating, 47 reviews
Top Guest favourite
A modern kitchen area is presented with a sleek design, featuring a gas stove and minimalist cabinetry. A dining table with four black chairs is set with tableware, while ambient lighting from a nearby lamp creates a soft glow. The space reflects a comfortable and functional dining environment.
Holiday home in Castiglion Fiorentino

La vita è bella

4.92 out of 5 average rating, 64 reviews
Guest favourite
The outdoor area features a large swimming pool surrounded by wooden decking and lounge chairs. A spacious villa is visible in the background, nestled among greenery. A covered outdoor kitchen area is also present, ideal for dining and gatherings.
Villa in Castiglion Fiorentino

Villa La Foce

4.95 out of 5 average rating, 21 reviews
Top Guest favourite
A spacious living room features an archway of exposed brick and stone, with large windows allowing natural light. A comfortable sofa is positioned around a coffee table, while a professional kitchen is visible in the background, complemented by wooden shelves filled with books.
Holiday home in Arezzo

Historic Arched Apartment in the Heart of Arezzo

5.0 out of 5 average rating, 153 reviews
Top Guest favourite
Home in Castiglion Fiorentino

Il Rifugio di San Filippino

5.0 out of 5 average rating, 7 reviews

When is the best time to visit Castiglion Fiorentino?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$152 AUD$138 AUD$139 AUD$153 AUD$159 AUD$163 AUD$183 AUD$152 AUD$162 AUD$195 AUD$159 AUD$153 AUD
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.

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