Castiglion Fiorentino Vacation Rentals from $108: Search Short-Term Rentals

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Vacation Rentals in Castiglion Fiorentino

"We‘ve spent two wonderful weeks with our two year old daughter and our dog. The house is beautifully located in the hills with no direct neighbours. The view is fantastic and we felt immediately at home in this beautiful house. We had a wonderful time and our hosts were just lovely. (We cannot say anything about the pool - except that it is huge - because we were there out of season in March when the pool was closed.)"

Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas

"Excellent views and the property was overall lovely. The nearby town San Quirico d'Orcia also had a good selection of restaurants and was a nice place to stroll in the evening."

Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

"Fabulous location just outside the entrance to the main part of town. Property is stylish in an olde worlde way, perfect for relaxation."

"Our host Maurizio, added quite a few extra layers of enjoyment to our stay. A brilliant host who went above and beyond to make our holiday truely memorable! We have invited him to come stay with us when he visits Australia. As for the farm house it’s self, an amazing experience to live like a true Italian. If you want to experience country life, I recommend La Rustica! Thank you Maurizio and Simonetta. ❤️"

"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "

$142 nightly

Jul 7 - Jul 8

Total includes taxes and fees

"The people here are authentic and welcoming! The building, rooms and facilities are gorgeous! One of our most beautiful stays in our many trips to Italy "

$296 nightly

Jul 9 - Jul 10

Total includes taxes and fees

"Gemäß der Anzeige und den schönen Fotos im Netz hatten wir einen super Plan – „unser Ferienhaus“ in Umbrien - eine Woche Umbrien erkunden, eine Woche am Pool genießen und eine Woche arbeiten…tja, dieser Plan ist eklatant gescheitert. Es wird kein Ferienhaus vermietet sondern ein Apartment im Erdgeschoss in einem bewohnten Haus mit einer älteren Frau, die nur italienisch spricht samt Hund und mind. vier Katzen sowie ständigen Besuchern; wir waren nie alleine und es war ständig laut. Das...

"Exvellent Location close to all towns in Tuscany Good communication w Manager"

"This is a charming house in a small town outside Cortona. Easily located near all the things you would want to see in the area. The host treated us like family and had homemade treats and wine waiting for our arrival. The house is perfectly suited for 4 people to stay and had a lot of charm. If you are looking to escape the hustle of daily life and relax this is the perfect location. "

"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."

$171 nightly

Jul 9 - Jul 10

Total includes taxes and fees

"We loved staying here. Absolutely great communication, super room, lots of dining options. Highly recommend this place."

$94 nightly

Jul 9 - Jul 10

Total includes taxes and fees

"The location and accommodations are perfect for a family. Nestled in the Italian countryside providing easy access to the nearby renaissance villages, art and landscapes and the people of Italy. The accommodations that Mieke has provided will only put a smile on your face."

"Hospitality of Sandro and his family is great. The house is unique and the partly private swiing pool super. In summer season airconditioning would be a welkome addition. "

$213 nightly

Aug 2 - Aug 3

Total includes taxes and fees

"We had a wonderful stay, the location was perfect for a short 15 minute walk into Montisi. The countryside setting was lovely and peaceful. We enjoyed being surrounded by beautiful nature, watching the deer every evening was delightful. We hope to return in the future. "

"We had five wonderful days in beautiful Toscana! Great atmosphere, wonderful location of the hotel and very reasonably priced. Eating at their restaurant was quite pricy however. Breakfast ok but excellent croissants and coffee! One of the reasons we picked this hotel was the laundry service which was advertised on hotels.com. No laundry service was available. "

$126 nightly

Jul 10 - Jul 11

Total includes taxes and fees

"Es ist das letzte Haus an der Straße in dem kleinen Ort, also kein Verkehr, nur Ruhe😌. Das Haus war sauber und ordentlich👍. Wir sind angekommen und haben uns gleich wohl gefühlt. Die Gastgeber sind sehr freundlich und hilfsbereit. Sie haben uns sehr gute Empfehlungen von sehenswerten in der Nähe geschickt, welche perfekt auf uns gepasst haben. Es war alles in allem eine sehr schöne Woche. Vielen Dank!!!😁"

"Amazing property with wonderful view of Lake Trasimino , 7 bedroom, 8 bathrooms, swimming pool, outside dining, great kitchen and several living rooms all with air conditioning. Shower gel annd tissues etc all provided. Adequately close to supermarkets. Sun beds were a bit tired/ broken."

"This worked out really well for our extended family across 3 generations. Lots of space, great amenities, and we loved Arezzo. Liliana is a brilliant host"

"We enjoyed especially the terrace because we had sunny weather"

"We had a wonder stay at the villa. Gave a true Tuscan countryside experience in a luxurious, comfortable and convenient location."

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Find out more about Castiglion Fiorentino

Everything you need to know about Castiglion Fiorentino vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Castiglion Fiorentino vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castiglion Fiorentino vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castiglion Fiorentino vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castiglion Fiorentino. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Castiglion Fiorentino in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $108 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Castiglion Fiorentino rentals

At Expedia, we put the best Castiglion Fiorentino vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Castiglion Fiorentino rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castiglion Fiorentino vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castiglion Fiorentino. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Castiglion Fiorentino properties

5/5 Excellent

Fantastic!

"It’s impossible to praise this hotel enough! What an amazing experience, from the care and concern after booking, to check-in and the attention to detail throughout our stay. The location is good, not too far to walk to local restaurants in Cortona but far enough to be tranquil. The hotel is spotless and well appointed. However what makes it an experience not to be forgotten is the staff. Everyone, from reception to housekeeping to restaurant to bar are amazing. Fantastic !!"

A verified traveler stayed at Monastero di Cortona Hotel & Spa

Posted 6 days ago

5/5 Excellent

"BEAUTIFUL complete resort…what you imagine when visiting Tuscany for an ultra high end experience. Everything was fantastic including the dining in all 3 restaurants…I highly recommend experiencing all 3 restaurants and at least 2x each (Osteria Del Borro should be Michelin rated with 2-stars, it’s heaven…I recommend their tasting menu that’s full of surprise extras, like 6 extra tastings). Best included breakfast ever in a beautiful setting with super large wine cellar. All 3 infinity pools are luxurious, provide full conveniences such as wait, bar, food, and towel services. The staff is awesome, so kind, courteous and identify guests are there for a high end experience. Take the wine & cheese tour it’s not only charming and interesting, but you’ll likely meet good folks/other guests. Our villa was absolutely magnificent and included a large steam shower, backyard perfect for wine tasting, complimentary bottle of IL Borro wine and unlimited drinks replaced 2x daily. IL Borro also celebrates the Ferragamo family (who we saw on property) and brand with select Ferragamo items for purchase, we indulged. Plan to send a case or 2 of wine home, their shipping to the States is completely reasonable and their IL Borro 2020 Tuscana (red - drinks like a Cabernet Sauvignon) is full bodied, well balanced, great flavors…we loved it, and is priced well. We cracked many of their whites and rose’s, both great, as we visited in June/summer. Needless to say, we will be back!! "

A verified traveler stayed at Il Borro - Relais & Châteaux

Posted 8 days ago

Villa di Piazzano - Small Luxury Hotel of the World

5/5 Excellent

"Our recent 4 night stay at Villa di Piazzano was truly perfect in every way! Celebrating our 40th wedding anniversary could not have been more enjoyed! Having booked our stay 6 mos in advance - I communicated many times via email during that time, seeking itinerary advice from the Conceirge. I always received very fast responses with creative ideas for our schedule that ended up proving most enjoyable. Cortona is a short, 10 minute drive away. Our arrival day was a dream, as we drove up the cypress lined drive which gave the feeling of arriving a royal residence! We were warmly greeted and instantly felt that our arrival was anticipated by the staff. We bonded very quickly with several of the team during our stay and experienced their excellent and warm hospitality. Our room, Luna Piena, proved to be absolutely perfect! Spotlessly clean and most roomy. We especially loved the bath area and roomy shower. Our room was accurately historical with every modern convenience. We enjoyed opening the windows each cool morning and loved listening to the birds sing. The property grounds were stunning! So much detail and care! The maintenance/gardening crew should be awarded! Amazing! We enjoyed wandering around the gardens and admiring all the flowers and plants! The swimming pool was crystal clear and the perfect temperature! Restaurant food was OUTSTANDING! I’m not sure how another resort hotel ANYWHERE in Tuscany region could top the experience we enjoyed at Villa di Piazzano! "

A verified traveler stayed at Villa di Piazzano - Small Luxury Hotel of the World

Posted 12 days ago

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Frequently asked questions

Are there vacation rentals in Castiglion Fiorentino?

Yes, you can find vacation rentals close to the most popular local attractions in Castiglion Fiorentino, or you can go with a more remote option if you're looking for relaxation. Castiglion Fiorentino is known for its wineries and churches. Make sure you have time to check out the monuments and art during your trip.

What are some of the best vacation rentals that Castiglion Fiorentino has to offer?

Farmhouse in the hills with panoramic view and swimming pool: Visitors give good reviews to this Castiglion Fiorentino vacation home rental, which is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Castiglion Fiorentino?

With 98 Expedia vacation rentals, you're sure to find just the right place for your Castiglion Fiorentino stay.

What can I see and do in Castiglion Fiorentino?

Cultural attractions include Municipal Art Gallery, whereas Val di Chiana is a spot to enjoy nature. Cassero Tower and Tennis Club Castiglionese are other places to visit while you're in town.

What are vacation rentals like in Castiglion Fiorentino?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Castiglion Fiorentino. Vacation rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a small group gathering.

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Castiglion Fiorentino Vacation Rentals

Check prices for these dates

Vacation Rentals in Castiglion Fiorentino

Farmhouse in the hills with panoramic view and swimming pool

Casanova - Panoramic Rooms and Suites

Hotel San Gregorio

17th century farmhouse with private pool and Wi-Fi and air conditioning

Abbadia Sicille Relais

Il Tosco

Villa with swimming pool and garden- San Feliciano, Trasimeno lake

Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi

Casina in authentic Tuscany

Il Poggio dell'Eremita

Residenza Fabroni

Luxury Cortona view hilltop Villa

Villa Graziella, Romantic Perugia

Hilltop house in the heart of Tuscany with private pool

Borgo Dolciano

Typical Tuscan Residence near the farm la Vialla

Villa with wonderful view of Lake Trasimeno and large panoramic swimming pool

Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

Montalcino Villa - Breathtaking Views of the Val d'Orcia

Find out more about Castiglion Fiorentino

Recent reviews of Castiglion Fiorentino properties

Monastero di Cortona Hotel & Spa

Il Falconiere - Relais e Chateaux

Precise Tale Poggio Alla Sala

Il Borro - Relais & Châteaux

Hotel Continentale

Hotel Villa Ricci

Villa di Piazzano - Small Luxury Hotel of the World

Albergo San Biagio

Hotel Panoramic

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