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Holiday rentals 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.

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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.
Apartment in Cortona
4.99 out of 5 average rating, 208 reviews

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.

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 130 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
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 in Macciano
4.97 out of 5 average rating, 221 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 in Ruscello
4.99 out of 5 average rating, 496 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 in Castiglion Fiorentino
4.9 out of 5 average rating, 235 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

Top guest favourite
The spacious living area features exposed stone walls and wooden beams, creating a rustic ambience. A comfortable leather sofa and a wooden dining table are present. A traditional stereo system is set on a ledge, while a staircase leads to the upper floor. A wine rack is visible in the background.
Flat in Montepulciano
4.97 out of 5 average rating, 150 reviews

Under the sunset, Montepulciano

In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away

Top guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.93 out of 5 average rating, 301 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Top guest favourite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Apartment in Pienza
5 out of 5 average rating, 146 reviews

Mascagni Farmhouse in Val d'Orcia Pienza

Risali le iconiche colline toscane fino a Mascagni Organic Farm, un'azienda biologica dove ti aspetta la tua nuova casa: un fienile del 1500 finemente ristrutturato immerso tra olivi e campi di grano. Rilassati prendendo una tazza di tè, raccogli rosmarini e lavande nel giardino con vista mozzafiato sulla Val d'Orcia. Riscopri la tua vera natura tra i campi incontaminati e gli olivi: qui le passeggiate e i giri in bici non hanno confini! Pronto a creare ricordi che dureranno tutta la vita?

Top guest favourite
An open kitchen area features a large window that offers a panoramic view of the surrounding landscape. A dining table is set for two, with modern chairs and colorful decor elements. Light reflects off the terracotta floor, highlighting the wooden beams overhead.
Loft in Montepulciano
5 out of 5 average rating, 500 reviews

La Piazzetta -Accogliente open space nel centro storico di Montepulciano

Versati un bicchiere di vino e accomodati di fianco al caminetto di questo open space dalla calda atmosfera tipicamente toscana: travi in legno, pavimento in cotto, pareti in pietra. Poi esci e ammira il magnifico panorama sulla Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana.

Top guest favourite
The farmhouse entrance is framed by two potted plants and orange pumpkins. A stone facade features a wooden door with gray shutters, complemented by a tiled roof. Natural surroundings are visible in the background, emphasizing the peaceful rural setting.
Home in Prato
4.98 out of 5 average rating, 142 reviews

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.

Top guest favourite
A serene outdoor space is framed by tall, leafy trees, creating a natural canopy. Within the gravel area, terracotta pots with greenery are visible, offering a sense of tranquility. The expansive view stretches across the hills and valleys of the surrounding landscape.
Flat in Cortona
4.96 out of 5 average rating, 186 reviews

Casa Le Contesse

È un piccolo appartamento, porzione della casa colonica dove vivo. È situato a piano terra, con accesso indipendente, in collina, in mezzo agli olivi, ad un km da Cortona. C'è possibilità di parcheggio, accesso privato, usufruire del giardino "superpanoramico''

Top guest favourite
An exterior view of a charming Tuscan house featuring warm stone walls. The surrounding garden includes manicured grass and potted plants. A spacious patio with a table for outdoor dining is visible, alongside a stone pathway leading to the entrance.
Guest house in Montefollonico
4.98 out of 5 average rating, 124 reviews

Casale Santa Barbara - Exclusive Apartment

Your private Tuscan retreat between Pienza and Montepulciano. A spacious 100 m² apartment for two, with exclusive access, a large private garden and breathtaking views over the Val d’Orcia hills. Elegance, calm and authenticity — just you… and Tuscany.

Popular amenities for Castiglion Fiorentino holiday rentals

When is the best time to visit Castiglion Fiorentino?

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Avg. price$138 SGD$125 SGD$126 SGD$147 SGD$158 SGD$153 SGD$166 SGD$138 SGD$147 SGD$177 SGD$144 SGD$139 SGD
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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 house rentals, over 40 apartment rentals to over 10 villa 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 house rentals in Castiglion Fiorentino have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Castiglion Fiorentino. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Castiglion Fiorentino have wifi?

    Absolutely! We offer over 30 apartment 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 $51 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    80 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!

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