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Holiday rentals in Castiglion Fiorentino

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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
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home
4.96 out of 5 average rating, 116 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Superhost
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
4.89 out of 5 average rating, 225 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 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.
Flat
4.97 out of 5 average rating, 136 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
A medieval stone tower stands tall against a clear blue sky, showcasing its historic architecture. The narrow road lined with greenery leads to the entrance, with the texture of the stonework and windows highlighted, inviting guests to explore its unique charm.
Tower
5 out of 5 average rating, 103 reviews

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Top guest favourite
A modern living area features a beige tufted sofa, complemented by a sleek coffee table and a vibrant area rug. A wood-burning stove stands beside a stacked wood display. Natural light filters through a window, providing a cozy ambience.
Home
4.9 out of 5 average rating, 176 reviews

Italian Internal

Knock on the door of this house, and an inspiring world will open up to you. The modern design, now luxurious, now fun, blends beautifully with the structures and airiness of the 18th-century rural complex, and offers a breathtaking panoramic window. The house is located within a residence, and use of the pool is shared with other guests in the complex. Surrounded by green hills, offers an ideal accommodation for families looking for a relaxing stay. The house is ideal for four people.

Top guest favourite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage
5 out of 5 average rating, 103 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

Guest favourite
A stone archway leads into a historic entrance, flanked by rugged walls covered with greenery. The pathway, lined with a metal railing, guides visitors through a tranquil setting enhanced by the natural surroundings.
Holiday home
4.94 out of 5 average rating, 284 reviews

La casina sulle Mura with garden

La Casina è situata nella parte alta di Cortona, nella zona denominata "il Poggio". Si puo' giungere in auto fino al suo ingresso. Il Centro citta' e' raggiungibile a piedi in pochi minuti, percorrendo strade e vicoli caratteristici. Gode di una splendida vista su Cortona e la Valdichiana. E' facile parcheggiare nelle vicinanze. Gli ospiti che giungono in treno in una delle stazioni vicine, su richiesta, possono essere prelevati e accompagnati a destinazione.

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
4.99 out of 5 average rating, 446 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
The image captures a vibrant town square in Cortona, featuring a historic clock tower and a series of stone steps leading to a large building. Outdoor seating is visible, with visitors enjoying the sunny day, and nearby buildings display a range of architectural styles.
Home
4.94 out of 5 average rating, 211 reviews

Casa del Passerino

Apartment located inside a historic building in Cortona, dating back to the 1500s, overlooking the city's main square... Our property, while condemning the war, dissociates itself from all racist behavior towards the Russian and Belarusian population. At Casa del Passerino, people of these nationalities are welcome and will be treated the same as everyone else. We look forward to seeing you in Tuscany!

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
4.98 out of 5 average rating, 244 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.

Top guest favourite
Farm stay
4.94 out of 5 average rating, 500 reviews

Poggio Bicchieri Holiday Farm - Poesia apartment

Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.

Guest favourite
A spacious bedroom features a large bed with soft linens and neatly arranged towels on the foot. Wall-mounted lights provide illumination, and a window offers natural light with a view of greenery outside. Exposed wooden beams add a rustic touch to the decor.
Apartment
4.97 out of 5 average rating, 126 reviews

Civetta golosa, Charming two-room apartment in the historic center

Cozy and practical two-room apartment on the second floor of a historic building, with an independent entrance and recently renovated. It is equipped with everything even for long stays. It has a comfortable double bedroom, bathroom and kitchen space. View of the city. Just 150 meters from the free parking lot in Piazzale del Mercato.

Popular amenities for Castiglion Fiorentino holiday rentals

When is the best time to visit Castiglion Fiorentino?

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Avg. price£69£63£67£85£92£89£96£80£85£103£84£81
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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.

  • 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 30 apartment rentals to over 10 house rentals, we've got you covered.

  • 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!

  • 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.

  • How much does it cost to stay in condo rentals in Castiglion Fiorentino?

    Experience the best of Castiglion Fiorentino with our condo rentals, starting at about $60 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 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Castiglion Fiorentino have a kitchen?

    Absolutely! We offer over 30 apartment rentals with a kitchen 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.

  • Do house rentals in Castiglion Fiorentino have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning 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.

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 £22 per night before taxes and fees

  • Verified guest reviews

    Over 1,740 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 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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