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Castiglion Fiorentino Vacation Rentals

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Our top choices for Castiglion Fiorentino vacation rentals

Townhouse in Castiglion Fiorentino

San Michele al Borgo
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is P7,295
P8,301 total
includes taxes & fees
Jan 8 - Jan 9, 2026
San Michele al Borgo

Townhouse in Loro Ciuffenna

Villa Cassia di Baccano
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is P7,109
P7,821 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Villa Cassia di Baccano

Townhouse in Chiusi

La Piccola Locanda
8.8 out of 10, Excellent, (8)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
La Piccola Locanda

Townhouse in Arezzo

THE MONNA LISA RESORT
9.6 out of 10, Exceptional, (8)
"Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. "
United States
Bart
The price is P8,773
P10,065 total
includes taxes & fees
Jan 3 - Jan 4, 2026
THE MONNA LISA RESORT

Townhouse in Civitella in Val di Chiana

Locanda Antico Borgo
9.2 out of 10, Wonderful, (20)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
The price is P6,918
P7,610 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Locanda Antico Borgo

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is P4,301
P4,939 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Abbadia Sicille Relais

Townhouse in Pienza

Affitacamere Maria Gabriella
9.8 out of 10, Exceptional, (51)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella

Townhouse in Montepulciano

Meublé Il Riccio
9.8 out of 10, Exceptional, (86)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio

Townhouse in Pienza

TuscanyLettings Studio&Room
10.0 out of 10, Exceptional, (1)
"メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。"
Japan
keita
The price is P5,603
P6,441 total
includes taxes & fees
Jan 9 - Jan 10, 2026
TuscanyLettings Studio&Room

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is P5,171
P5,966 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Residenza Fabroni

Residence in Pienza

Hotel San Gregorio
3.0 star property
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is P11,208
P12,745 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hotel San Gregorio

Townhouse in Montepulciano

La Locanda di San Francesco
9.8 out of 10, Exceptional, (131)
"Great room-great staff-great location"
United States
Richard
The price is P10,713
P12,061 total
includes taxes & fees
Jan 18 - Jan 19, 2026
La Locanda di San Francesco

Townhouse in Pienza

PienzaLettings Suites
10.0 out of 10, Exceptional, (1)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is P5,043
P5,825 total
includes taxes & fees
Jan 6 - Jan 7, 2026
PienzaLettings Suites

Townhouse in Monte San Savino

DormiVeglia B&B
10.0 out of 10, Exceptional, (27)
"This was our favourite B&B. The owner Simona was absolutely wonderful. The hot tub in our room was out of this world. If you have the chance to visite this gem…DO IT!!"
Canada
Claude
DormiVeglia B&B

Townhouse in Arezzo Centro Storico

Cameracaffè Centro
8.6 out of 10, Excellent, (179)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is P5,356
P6,308 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Cameracaffè Centro

Residence in San Quirico d'Orcia

Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
Casanova - Panoramic Rooms and Suites

Townhouse in Subbiano

Villa La Ginestra
9.6 out of 10, Exceptional, (5)
"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."
Canada
Philippe
Villa La Ginestra
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.
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Top Castiglion Fiorentino Hotel Reviews

Find out more about Castiglion Fiorentino

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:

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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.

How many vacation rentals are there in Castiglion Fiorentino?

With 59 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. Tennis Club Castiglionese and Cassero Tower 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.