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Apartment vacation rentals in Castiglion Fiorentino

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Top-rated apartment rentals in Castiglion Fiorentino

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An outdoor terrace features modern lounge furniture, including two sun loungers and a seating arrangement with a coffee table. A small pool is present, surrounded by greenery, and decorative items enhance the inviting setup.

Apartment in Arezzo

4.96 out of 5 average rating, 113 reviews

GOLD appartamento in centro storico Sweet Tuscany

CODE:051002CAV0052 L'appartamento Gold da poco ristrutturato, si trova dentro alle mura storiche di Arezzo a pochi passi dai principali siti di interesse storico architettonico come musei, chiese,la bellissima Piazza Grande dove si svolge la fiera antiquaria ogni primo week and del mese e la giostra del Saracino,vicino alla bellissima fortezza Medicea completamente restaurata.Passeggiando si possono raggiungere molti ristoranti dove gustare la nostra cucina ed i piatti tipici della nostra terra.

Top guest favorite

A small balcony is featured with two black woven chairs flanking a round table. On the table, a bottle and two glasses are set against a backdrop of panoramic views of rolling hills and terracotta rooftops under a partly cloudy sky.

Apartment in Cortona

4.99 out of 5 average rating, 164 reviews

Cortona’s Rooftop Nest

L’appartamento è sito in pieno centro storico proprio di fronte alla meravigliosa chiesa di San Francesco e a pochi passi dalla piazza principale.Arredato in stile country chic e dotato di tutti i comfort.Ospita 4 persone.Ventilatori nelle camer The apartment is located in the historic center right in front of the wonderful church of San Francesco and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can host up to 4 people. Fan in the rooms.

Top guest favorite

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

4.96 out of 5 average rating, 106 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 favorite

A spacious bedroom features a double bed adorned with a yellow bedspread. Natural light floods in from wide glass doors leading to a balcony with views of the valley. A cozy seating area includes two armchairs and a small table, complemented by decorative curtains.

Apartment in Montepulciano

5 out of 5 average rating, 124 reviews

Stuart White Tea Central Panoramic & Garden

Offering ample space, the apartment features two double bedrooms, two full bathrooms, and a living room with a kitchen. The bedroom balconies offer stunning views of the valley and natural light. Its proximity to all town amenities ensures convenience, while a delightful café downstairs provides a delectable gourmet breakfast. It has also access to a secluded, terraced backyard garden. It provides a comfortable retreat perfect for long term stays. A public parking is available nearby.

Two comfortable chairs are positioned on a lush green lawn, complemented by a small wooden table. A basket of vibrant yellow flowers is nearby, set against a backdrop of rolling hills and cypress trees under a clear blue sky.

Apartment in Monticchiello

4.97 out of 5 average rating, 158 reviews

Casa Bonari - un paradiso per gli occhi

Casa Bonari è un appartamento indipendente su un unico livello all'interno di una villa ai piedi di Monticchiello. E' composto da 3 camere da letto, 2 bagni, cucina attrezzata e salotto. Le stanze sono luminose e arredate in stile toscano, con vecchi mobili di famiglia ristrutturati uniti ad elementi contemporanei. La cucina è completamente attrezzata e l'appartamento circondato su ogni lato da un grande giardino, così che tutte le stanze vantano un bellissimo panorama sulla campagna.

Top guest favorite

A spacious piazza is surrounded by elegant medieval architecture, featuring a central hexagonal area with open-air seating. Stone pathways lead to various shaded spots, while umbrellas provide shelter for patrons. Beautiful clouds drift overhead, enhancing the vibrant scene of daily life in the historical center.

Apartment in Arezzo

5 out of 5 average rating, 113 reviews

Piazza Grande Boutique Apartment

Affacciato sulla più bella piazza del centro storico di Arezzo, dove si svolge la rievocazione della Giostra del Saracino, il Piazza Grande Boutique Apartment è situato al secondo piano di un palazzo medievale, con vista sui bellissimi palazzi e le Logge Vasariane ed è una location unica nel suo genere. L'arredamento, opera della contessa Cesaroni Venanzi è stato realizzato con bellissimi mobili antichi reinterpretrati in chiave moderna ed arricchiti da contaminazioni contemporanee.

Top guest favorite

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

4.96 out of 5 average rating, 169 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 favorite

A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.

Apartment in Castelnuovo Berardenga

4.93 out of 5 average rating, 165 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

A small wooden table set for two is adorned with fine china cups and a delicate flower vase. The balcony offers a panoramic view of the rolling hills, as the sun sets, casting warm hues over the landscape.

Apartment in Montepulciano

4.94 out of 5 average rating, 217 reviews

I Tramonti di Eramo , Montepulciano centro.

Benvenuti a Montepulciano, il gioiello delle colline toscane! Il nostro appartamento nel cuore del centro storico offre una vista mozzafiato sulla campagna circostante, regalando un'esperienza autentica e indimenticabile. Potrete uscire di casa e assaporare l'atmosfera storica di Montepulciano. A pochi passi avrete la straordinaria Piazza Grande, ristoranti di ottima qualità e servizi di ogni genere. La Toscana vi aspetta per vivere emozioni uniche.

Top guest favorite

The bedroom features a spacious double bed adorned with soft linens and cushions, complemented by subtle bedside lamps. Exposed wooden beams highlight the ceiling, while natural light filters through a window, adding warmth to the serene, neutral color palette.

Apartment in Cortona

4.97 out of 5 average rating, 377 reviews

Cortona Shabby Chic House (independent & balcony)

Cortona Shabby Chic con balcone privato e totale privacy, perfetto relax. Il mio alloggio è situato in pieno centro storico a soli pochi passi dalle piazze e vie principali. Questo grazioso appartamento è di recente ristrutturazione e può ospitare fino a 3 persone. Appartamento indipendente con entrata singola tutto in un solo piano. Arredato con cura e dotato di tutti i comfort

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Popular amenities for Castiglion Fiorentino apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

Top guest favorite

A cozy room features a spacious bed against a white wall, complemented by rustic wooden beams and an inviting reading chair. A dining table is set with floral arrangements and tableware. Natural light is seen streaming through the open door leading to the garden.

Apartment in Monticchiello

5 out of 5 average rating, 54 reviews

Casa Tòrta - comfort room

Top guest favorite

The exterior of a charming farmhouse is displayed in the evening light, showcasing a stone facade and arched window illuminating the interior. A spacious lawn surrounds the building, featuring neatly arranged chairs and a table, complemented by lush greenery and nearby trees.

Apartment in Chiusi

5 out of 5 average rating, 6 reviews

The Barn - Apartment for 5 people with kitchenette

An outdoor space is featured, showcasing a stone structure with a door leading inside. A rustic table is set with glasses and plates, surrounded by vibrant yellow flowers and green shrubs, creating a serene environment for dining.

Apartment in San Leo Bastia

5 out of 5 average rating, 30 reviews

Hamlet San Biagio a Colle - Casa di Venere

Top guest favorite

A spacious bedroom features a comfortable queen size bed with fresh linens. Original wooden beams are visible overhead, adding character. A bedside lamp provides soft lighting, while a window allows natural light to fill the room. Tastefully restored furniture complements the inviting atmosphere.

Apartment in Viciomaggio

4.99 out of 5 average rating, 72 reviews

[L'Antico Frantoio] Relax 5* w/ Private Parking

Top guest favorite

A welcoming living area features a white fabric sofa adorned with neutral and brown cushions. A coffee table sits at its center, decorated with books and a vase of white orchids. The walls are adorned with framed art, enhancing the cozy atmosphere.

Apartment in Pogi

5 out of 5 average rating, 19 reviews

Borgo Iesolana Family Suite Superior

Apartment in Castiglion Fiorentino

5 out of 5 average rating, 3 reviews

Ortensia (10 pax)

Top guest favorite

An outdoor dining area features a large table set for four under a spacious umbrella. Two lounge chairs are positioned nearby, surrounded by stone pavers and potted plants. The charming facade of the villa can be seen in the background, enhancing the peaceful ambiance.

Apartment in Arezzo

4.96 out of 5 average rating, 85 reviews

Villa Medici Donnini Deluxe Apartment

A spacious outdoor pool is set against a backdrop of lush greenery and cypress trees. The inviting turquoise water reflects the clear sky, while lounge chairs are positioned nearby. The landscape gently slopes upward towards a cluster of rustic buildings surrounded by manicured gardens.

Apartment in Asciano

4.82 out of 5 average rating, 11 reviews

Affitti Brevi Siena - Toscana con piscina da sogno

Private apartment rentals

An aerial view captures a historic farmhouse set amidst expansive olive groves. Lush greenery surrounds the property, with neatly arranged trees and a sparkling swimming pool visible. The outdoor space features a well-maintained garden, ideal for relaxation and leisure.

Apartment in Cortona

5 out of 5 average rating, 10 reviews

Casale La Cedrina(Il Melograno)

A spacious living area features large windows allowing natural light to fill the room. The space includes a comfortable seating arrangement, a dining table set with serving pieces, and distinctive ceiling structures. A warm wooden floor complements the modern decor and exposed brick wall.

Apartment in Arezzo

4.89 out of 5 average rating, 56 reviews

modus apartments

Top guest favorite

The historic stone building is illuminated at dusk, enhancing its architectural features. A tranquil swimming pool reflects the soft light, surrounded by landscaped olive trees and a stone wall, creating a serene outdoor space.

Apartment in Montone

4.97 out of 5 average rating, 39 reviews

Dependance nel castello del Cardaneto

Top guest favorite

A glimpse into the welcoming living area reveals a patterned sofa and a vintage coffee table. Artistic wall hangings complement the space, while natural light filters through the entryway. A wooden desk with a sewing machine is positioned nearby, adding a touch of nostalgia.

Apartment in Montepulciano

5 out of 5 average rating, 19 reviews

WiFiFiberCozyStudioMontepulciano

Top guest favorite

A serene outdoor lounge area is framed by lush greenery and features a wooden gazebo with flowing white drapes. Comfortable seating is arranged beneath shaded areas, complemented by a rustic wooden planter with a small tree. Clear blue skies are visible above.

Apartment in Siena

4.97 out of 5 average rating, 36 reviews

Palazzo del Papa Suites standard

Top guest favorite

A warm and inviting open space features a wooden dining table surrounded by chairs, illuminated by natural light from several windows. A red sofa is positioned nearby, while a television and kitchen appliances, including a stove and oven, are visible in the background.

Apartment in Montepulciano

4.96 out of 5 average rating, 97 reviews

Casa Crociani - Amazing Pool & Free Parking

Top guest favorite

A serene terrace space is presented, featuring a round glass table surrounded by white iron chairs. Greenery and blooming flowers are placed in terracotta pots, complemented by a trellis above providing shade. A charming view of terracotta rooftops and clear blue sky is visible in the background.

Apartment in Pienza

5 out of 5 average rating, 36 reviews

Live Like a Local & Private Concierge Service

Top guest favorite

A bright kitchen area features modern white cabinetry and a wooden countertop, complemented by a dining table with four white chairs. Large windows allow natural light to fill the space, providing a scenic view of the outdoors. A patterned backsplash adds visual interest.

Apartment in Montepulciano

5 out of 5 average rating, 28 reviews

WiFiFiber LargeApartment with view inMontepulciano

Apartment rentals with a hot tub

A bright living area features a wooden table with a wine bottle and glass in the foreground. Large glass doors open to a patio, revealing countryside views and two outdoor chairs facing the tranquil landscape.

Apartment in San Giovanni d'Asso

5 out of 5 average rating, 21 reviews

Podere Ferranino #Cimabue Townhouse

A sunlit outdoor area features comfortable lounge chairs in vibrant colors beside a hot tub. Olive trees and shrubs surround the space, providing a serene backdrop. A gentle slope of green grass continues toward distant hills, enhancing the tranquil atmosphere.

Apartment in Montevarchi

4.88 out of 5 average rating, 105 reviews

Apartment with garden in the heart of Tuscany

Top guest favorite

Apartment in Castelmuzio

5 out of 5 average rating, 22 reviews

Appartamento bel Tramonto

A tranquil outdoor area is highlighted by a clear swimming pool, surrounded by well-maintained grass and lined with tall cypress trees. A charming stone house is visible in the background, completing the scenic countryside view.

Apartment in Monteroni d'Arbia

4.95 out of 5 average rating, 66 reviews

San Giovanni in Poggio, Crepuscolo app. 60 mq

Aerial view of a villa surrounded by lush greenery and vineyards. A serene pool is shaped organically, nestled among olive trees, while the two-story villa is highlighted by its terracotta roof and rustic stone facade. The landscape extends to rolling hills in the background.

Apartment in Lucignano

4.78 out of 5 average rating, 50 reviews

Podere Pozzangone - Your Tuscany Home

Top guest favorite

An ancient stone well is positioned in the foreground, showcasing intricate carvings and a circular top. In the background, an impressive stone building features a tower and windows, accented by flags. The scene captures the historical charm of Montepulciano's central square under a clear blue sky.

Apartment in Montepulciano

4.92 out of 5 average rating, 147 reviews

Charming House in Montepulciano

A panoramic terrace is presented, showcasing a spacious outdoor area adorned with sun loungers. The railing features distinctive decorative elements, and views extend over the surrounding landscape, with charming rooftops and greenery visible in the distance under a clear blue sky.

Apartment in Bettolle

4.91 out of 5 average rating, 11 reviews

Residenza Villa Clara

An outdoor dining area is set beneath a pergola adorned with grapevines, offering a scenic view of the surrounding hills and valleys. A table is arranged with dinnerware, surrounded by metal chairs, creating an inviting space for meals while enjoying the landscape.

Apartment in Montalcino

4.92 out of 5 average rating, 65 reviews

Podere Belsogno

Quick stats about apartment rentals in Castiglion Fiorentino

Total rentals
40 properties
Nightly prices starting at
R883 ZAR before taxes and fees
Total number of reviews
520 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool

Destinations to explore