Photo by Sophia Field

Castiglion Fiorentino Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Castiglion Fiorentino

Pool
Farmhouse in the hills with panoramic view and swimming pool
9.6 out of 10, Exceptional, (58)
"A super holiday. The location is superb with many places of interest within a 1 hour drive. Pool was maintained well and clean. We had a great 2 weeks."
Farmhouse in the hills with panoramic view and swimming pool
Exterior
Giglio Dorato is an antique restored stone farmhouse with indipendent apartments
Giglio Dorato is an antique restored stone farmhouse with indipendent apartments
Pool
Casa Lina - private pool and garden to enjoy with friends or family
10.0 out of 10, Exceptional, (1)
"Tout était parfait! Contact avec les propriétaires excellents."
Casa Lina - private pool and garden to enjoy with friends or family
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
Casanova - Panoramic Rooms and Suites
3.0 star property
9.4 out of 10, Exceptional, (18)
"The location is great, you have beautiful Tuscan view in front of yard. The room and bathroom are large, clean and modern with full kitchen. Good choice of breakfast, restaurant onsite is good for dinner. Free parking is good for travel by car."
The price is HK$1,373
per night
2 Jun - 3 Jun
Casanova - Panoramic Rooms and Suites
Seasonal outdoor pool, pool loungers
Hotel San Gregorio
3.0 star property
9.2 out of 10, Wonderful, (99)
"Very nice staff, great service, super clean. Will stay again."
The price is HK$1,267
per night
27 May - 28 May
Hotel San Gregorio
Fridge, microwave, oven, stovetop
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
10.0 out of 10, Exceptional, (101)
"Stephano goes out of his way to make his guests feel at home. The place was comfortable and spotless. We enjoyed getting to know our host and his city. The kitchen is well appointed with a well stocked wine rack. Read through the reviews, they are accurate! Comfortable bedding, lovely surroundings and, oh yes, a wonderful bakery across the street. Highly recommended!"
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Pool
House with garden and panoramic view over Lake Trasimeno
9.8 out of 10, Exceptional, (36)
"Lovely property in a fantastic location far from the Madding Crowd, not that we found a crowd anywhere we visited. The only problem we encountered was the aggressive mosquitoes which stopped us using the pool. Other than that it was a great week away."
House with garden and panoramic view over Lake Trasimeno
Outdoor dining
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.8 out of 10, Exceptional, (54)
"This is a wonderful property in a quiet area, but only a short walk to the piazza and restaurants. The only improvement I would recommend is the shower caddy; all of my travel sized items kept falling out of it."
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Terrace/patio
Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (142)
"Great experience "
The price is HK$1,079
per night
30 May - 31 May
Abbadia Sicille Relais
Property grounds
Big house
7.8 out of 10, Good, (11)
"The house and location are perfect for a family holiday, the pool is lovely and there are plenty of covered areas in the garden in which to relax when the sun gets too hot! The proprietors are very accommodating and fixed any issues (washing machine failed during our stay) immediately. The only thing to be aware of is that the region near the lake does suffer from mosquitoes which come out in the evening - so take repellent with you as it’s expensive in Italy!"
Big house
Pool
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
10.0 out of 10, Exceptional, (98)
"We were group of 16 adults and three children under the age of three. Sonja and Diego could not have been better hosts! They are truly lovely people! Everything was absolutely perfect! The villa is stunning and very child friendly! We opted to have Sonja cook breakfast and dinner for us each day, and her food was absolutely delicious! You must try their pizza and bbq! We enjoyed the tennis court, feeding the horses, and day trips to Siena, Florence, and Montepulciano. The villa location is...
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
Outdoor pool
Traditional stone cottage in rural, tranquil and quiet location built in 1799
10.0 out of 10, Exceptional, (30)
"Wow. If I could click 10 stars for a review I would. What a fantastic stay with super fantastic people. Our visit was at the end of March and it was beautiful. I can't imagine how beautiful this place would be later in the year. As for the hosts..... they could not have been more friendly and accommodating. They made us feel more like family then guests. I recommend 100% anytime of the year. Not to mention... there is not a more beautiful part of Tuscany."
Traditional stone cottage in rural, tranquil and quiet location built in 1799
Interior
Delcorto Suites
10.0 out of 10, Exceptional, (12)
"This was a beautiful property well maintained and perfectly located in a historic building. The breakfast was delicious, Ricardo the host was wonderful and our room was space and comfortable! The only comment was without A/C the windows needed to stay open and the street was loud."
The price is HK$1,338
per night
6 Jun - 7 Jun
Delcorto Suites
Lobby
Residenza Fabroni
9.0 out of 10, Wonderful, (63)
"The room has excellent views in a space that oozes character. The shared spaces and rooftop terrace were a very cool added bonus. We stayed in the blue suite and found it spacious and comfortable. The only slight issue was a faint odor coming from the second bedroom. We didn’t use that room and closing the door solved the problem for the rest of the suite, but it is worth noting. I know some people will complain that it is on the third floor and there is no lift, but frankly if this is an issue...
The price is HK$860
per night
27 May - 28 May
Residenza Fabroni
Pool
Tara by Interhome
8.8 out of 10, Excellent, (8)
"Beautiful guesthouse! Kitchen had everything we needed. Bigger bath towels would have been better. Difficult to communicate with the landlords as they had no English and I had very little italian"
Tara by Interhome
Pool
17th century farmhouse with private pool and Wi-Fi and air conditioning
9.4 out of 10, Exceptional, (32)
"This property is located approx 5km from the beautiful town of Arezzo. There is a bus every hour, daily, from Tregozanno, where the property is actually located, to Arezzo. It is very rustic and in a beautiful setting. So relaxing. And, because it’s not right in town, the best of both worlds. There are no restaurants in Tregozanno but there is a great butcher and deli/mini market. There is also a pharmacy and bar! Maurizio, the owner lives next door and is the loveliest, most helpful human being...
17th century farmhouse with private pool and Wi-Fi and air conditioning
Pool
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, (55)
"Where to even begin? We loved everything about our stay. Stefania was wonderful, and responsive to our many questions before we even arrived. Upon arrival, it felt like a dream. The Villa is beautiful, private, and expansive. The property is huge, with lots of olive trees, fig trees, and places for the kids to play and explore. And not to mention the stunning pool, which overlooks the most incredible views of Cortona. We were pleased to find a ping pong table, and just absolutely loved the pool...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
TV
Casa Campau by Interhome
9.0 out of 10, Wonderful, (2)
Casa Campau by Interhome
Property entrance
Il Tosco
10.0 out of 10, Exceptional, (87)
"Il Tosco is a quiet, clean and charming place to stay while traveling in Tuscany. The common rooms are cozy and the elegant breakfasts are the best we encountered in Italy. This is a wonderful place to stay with a local quality. Well worth the higher cost. "
The price is HK$2,227
per night
11 Jun - 12 Jun
Il Tosco
Exterior
Magnificent stone farmhouse in the heart of Tuscany
10.0 out of 10, Exceptional, (24)
"The property has beautiful views and a peaceful, remote location. It is well equipped for cooking meals and they conveniently provide a starter supply of necessities (kitchen spices, hand soap, laundry soap, toilet paper, etc.). The property owner, as well as the local property manager, were both very responsive to our questions and the check in and out processes are simple. We thoroughly enjoyed our stay."
Magnificent stone farmhouse in the heart of Tuscany
Don't see what you're looking for?
See all available properties in Castiglion Fiorentino
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Castiglion Fiorentino you may be interested in

Pool
Farmhouse in the hills with panoramic view and swimming pool
9.6 out of 10, Exceptional, (58)
"A super holiday. The location is superb with many places of interest within a 1 hour drive. Pool was maintained well and clean. We had a great 2 weeks."
Farmhouse in the hills with panoramic view and swimming pool
Exterior
Giglio Dorato is an antique restored stone farmhouse with indipendent apartments
Giglio Dorato is an antique restored stone farmhouse with indipendent apartments
Sauna, hot tub, steam room, massages
Monastero di Cortona Hotel & Spa
5.0 star property
10.0 out of 10, Exceptional, (166)
"Excellent experience!!! Very attentive staff in ALL areas. Room was beautiful!! Breakfast was outstanding!!! Spa space was amazing!!!! A few tight corners but well worth the drive!!!! Love, love, loved the stay! "
The price is HK$2,585
per night
6 Jun - 7 Jun
Monastero di Cortona Hotel & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Search for holiday rentals in Castiglion Fiorentino on Expedia! You can easily find your home rentals, villas, holiday apartments in Castiglion Fiorentino using one of the methods below:

  • View our selection of featured holiday rentals in Castiglion Fiorentino
  • Use the map to find apartments and other holiday homes in the Castiglion Fiorentino neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Castiglion Fiorentino while they last

Look no further and take a look at our great range of rental properties in Castiglion Fiorentino!

Frequently asked questions

Are there holiday rentals in Castiglion Fiorentino?

Yes, there are holiday rentals close to the most popular sights in Castiglion Fiorentino, or you can select a more secluded option if you're looking for a relaxing stay. Castiglion Fiorentino is known for its wineries and churches. Make sure you have time to check out the monuments and art during your trip.

How many holiday rentals are there in Castiglion Fiorentino?

With 97 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Castiglion Fiorentino?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Castiglion Fiorentino. Holiday rentals provide amenities such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family trip.

Recent reviews of Castiglion Fiorentino properties
Expedia verified reviews

Hotel San Michele

Hotel San Michele

5/5 Excellent
Cozy in Cortona
"We stayed for one night. Lovely and great location. "
A verified traveller stayed at Hotel San Michele
Posted 1 day ago
Hotel San Michele