A historic town with a prominent church tower, surrounded by rolling hills and vineyards.

Castiglion Fiorentino Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Castiglion Fiorentino vacation rentals

Exterior

1. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is P8,798
P9,959 total
includes taxes & fees
Aug 25 - Aug 26
San Michele al Borgo
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

2. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (39 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is P7,927
P9,144 total
includes taxes & fees
Sep 10 - Sep 11
iConic Wellness Resort
Lunch and dinner served

3. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (43 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is P15,142
P16,937 total
includes taxes & fees
Aug 16 - Aug 17
Castello di Gargonza
Courtyard

4. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay here! The hosts and staff were super warm and friendly. Breakfast had a wide choice and we liked the evening drinks set up too! The hotel doggies were definitely a highlight ☺️ we’d love to come back!"
United Kingdom
Shelby
The price is P14,917
P16,692 total
includes taxes & fees
Aug 17 - Aug 18
Fontelunga Hotel & Villas
Private spa tub

5. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (29 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is P7,813
P8,875 total
includes taxes & fees
Aug 13 - Aug 14
DormiVeglia B&B
Lobby

6. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (23 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is P8,956
P10,135 total
includes taxes & fees
Aug 16 - Aug 17
B&B Piccolo Hotel
Porch

7. Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (192 reviews)
"Very convenient and a beautifull terrasse to have breakfast with an amazing vue on Arezzo!"
France
Alexandre
The price is P5,593
P6,576 total
includes taxes & fees
Aug 28 - Aug 29
Cameracaffè Centro
Front of property

8. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is P6,259
P7,166 total
includes taxes & fees
Aug 25 - Aug 26
Vicolo Della Scala Rooms - La Luna
Terrace/patio

9. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (178 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is P11,533
P12,897 total
includes taxes & fees
Aug 23 - Aug 24
Abbadia Sicille Relais
Exterior

10. Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (20 reviews)
"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 P7,204
P7,925 total
includes taxes & fees
Aug 13 - Aug 14
Locanda Antico Borgo
Property entrance

11. Palazzo Tarlati Residenza d'Epoca

Palazzo Tarlati Residenza d'Epoca
Civitella in Val di Chiana
8.0 out of 10, Very Good, (3 reviews)
"Small family-owned inn located in center of Civitella in Val di Chiana. Room was comfortable and included all we needed. It was cold upon check-in which the co-owner tried to remedy with a space heater. It took a while. The room warmed up after the first night. The other co-owner kindly offered me our first night complimentary. (Thank you again.). The breakfast was simple and included fruit, juice, yogurt, sliced cheese and cold cut, packages sweets, tea, coffee and water. The owners were...
United States
Marco
The price is P7,651
P8,416 total
includes taxes & fees
Aug 13 - Aug 14
Palazzo Tarlati Residenza d'Epoca
View from room

12. B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.0 out of 10, Very Good, (81 reviews)
"Very accessible and easy accommodation. Very pleasant room and reasonable breakfast. Within walking distance of train station and city centre."
Australia
Tina
The price is P4,957
P5,873 total
includes taxes & fees
Aug 19 - Aug 20
B&B 52cento
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

Grand Hotel Admiral Palace

Grand Hotel Admiral Palace

10/10 Excellent
"Na"
Vivian 9-night trip
Posted 20 hours ago
Grand Hotel Admiral Palace

Find out more about Castiglion Fiorentino

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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 89 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.