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Vacation rentals in Castiglion Fiorentino

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Top-rated vacation rentals in Castiglion Fiorentino

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Top guest favourite
A charming exterior view of the accommodation is presented, featuring a white building with wooden windows and a bell tower. Lush greenery and terracotta pots filled with plants adorn the garden area, while an outdoor table with an umbrella offers a shaded seating option.
Apartment in Castiglion Fiorentino
4.98 out of 5 average rating, 58 reviews

"Borgo Sant'Andrea al Pozzo" in Ancient Abbey

Residenza completamente ristrutturata all'interno di un'antica Abbazia, già citata nel 1114 d.C. e proprietà dei frati Camaldolesi nel XII secolo. A pochi metri le mura storiche di Castiglion Fiorentino risalenti al 1200 d.C. e Porta Romana. Dista 500 mt a piedi dal centro storico di Castiglion Fiorentino e 15 min in auto da Cortona. Un soggiorno unico, tra storia e natura, in un contesto rilassante e riservato. Punto strategico per poter visitare Siena, Pienza, Anghiari, Arezzo, Cortona.....

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
4.98 out of 5 average rating, 187 reviews

Chicca: luminosa e panoramica nel centro storico

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
A cozy window nook is shown with a domesticated cat sitting beside a potted plant filled with pink flowers. A glass of sparkling water rests nearby, and a book is placed on the wooden surface, creating an inviting atmosphere.
Condo in Castiglion Fiorentino
4.95 out of 5 average rating, 20 reviews

Casa Letizia appartamento centro storico

Delizioso appartamento in palazzo storico medievale, nel centro storico di Castiglion Fiorentino, a due passi dalla torre del Cassero e dal Loggiato Vasariano, su Corso Italia. Vicino a enoteca, pizzeria, negozi, ristoranti, locali e bar situati nel centro, accanto a servizi (banca, posta, uffici). A soli 2 minuti a piedi dal parcheggio proprio fuori le mura. Vicino alla stazione dei treni (circa 800 m.) Vicino alla stazione degli autobus (circa 150 m). Parcheggio gratuito pubblico a 50 m.

Top guest favourite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Apartment in Montepulciano
4.97 out of 5 average rating, 116 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 for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

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.
Guesthouse in Macciano
4.97 out of 5 average rating, 194 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, 460 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
4.91 out of 5 average rating, 220 reviews

Tuscan charm of villa - countryside

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
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.
Guesthouse in Montefollonico
4.97 out of 5 average rating, 112 reviews

Casale Santa Barbara - Exclusive Apartment

At a glance: • Location: perfect entry door to the Val d’Orcia between Pienza (8,5 km) and Montepulciano (8,5 km). • Charming warm old stones Tuscan house – completely restored in 2016 • Big apartment (100m2), designed for 2 persons, completely independent, fully furnished, Tuscan style with modern equipment. • Exclusivity: we are living on the 1st floor; the ground floor is yours. You are our only guests. • Spacious private garden (+ 300m2) • Stunning view on the Tuscan hills.

Top guest favourite
A spacious living area features a comfortable purple sofa and striped poufs, complemented by a classic wooden sideboard and elegant lamps. Warm colors adorn the walls, and a large artwork adds character. Natural light enters through multiple windows, enhancing the inviting ambiance.
Apartment in Cortona
4.97 out of 5 average rating, 176 reviews

CasaNella: luminosa, centrale e panoramica

Accogliente, elegante e delizioso appartamento nel centro di Cortona, con un panorama incantevole che spazia dal Lago Trasimeno alla Valdichiana. Accuratamente arredato, è il luogo ideale per trascorrere qualche giorno in questa meravigliosa cittadina. A due passi dalla strada principale, ma in una posizione silenziosa e panoramica. Parcheggio gratuito a breve distanza. Dotato di riscaldamento ed aria condizionata. Disponibile WiFi ad alta velocità. Ottimo per smartworking.

Top guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 425 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Top guest favourite
A stone exterior is showcased, with a staircase leading up to the entrance. A shaded area features outdoor seating, including a table and chairs. Potted plants line the pathway, and greenery provides a serene backdrop, enhancing the outdoor living space.
Home in Prato
4.99 out of 5 average rating, 130 reviews

Tofanello Turquoise Luxury 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 orange apartment. Orange: https://www.airbnb.com/rooms/plus/9429730

Top guest favourite
A serene bedroom space features a spacious bed adorned with soft, neutral-toned linens. Sheer white drapes create a cozy atmosphere, while the open doors offer a view of the lush outdoors, inviting natural light into the room.
Farm stay in Arezzo
4.98 out of 5 average rating, 242 reviews

Esplora la natura al centro di Vigneti Chianti

Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.

Popular amenities for Castiglion Fiorentino vacation rentals

Quick stats about vacation rentals in Castiglion Fiorentino

  • Total rentals

    90 properties

  • Nightly prices starting at

    $42 CAD before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Family-friendly rentals

    60 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    40 properties have a pool

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  5. Castiglion Fiorentino