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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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 NT$4,605
NT$5,212 total
includes taxes & fees
Sep 15 - Sep 16
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, (40 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is NT$2,763
NT$3,260 total
includes taxes & fees
Oct 11 - Oct 12
iConic Wellness Resort
Deluxe Apartment, City View | Soundproofing, iron/ironing board, WiFi (free)

3. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is NT$4,505
NT$5,065 total
includes taxes & fees
Sep 16 - Sep 17
CASA AMBRA
Porch

4. 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 NT$2,803
NT$3,304 total
includes taxes & fees
Sep 22 - Sep 23
Cameracaffè Centro
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | 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 NT$3,614
NT$4,122 total
includes taxes & fees
Oct 4 - Oct 5
DormiVeglia B&B
Lobby

6. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is NT$5,009
NT$5,657 total
includes taxes & fees
Sep 23 - Sep 24
B&B Piccolo Hotel
Exterior

7. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very Good, (25 reviews)
"Good house for one night. "
Germany
Heiner
The price is NT$2,663
NT$3,076 total
includes taxes & fees
Sep 14 - Sep 15
Artisti del Cavallo Tourism
Courtyard

8. 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 NT$10,368
NT$11,552 total
includes taxes & fees
Sep 19 - Sep 20
Fontelunga Hotel & Villas
Luxury Double or Twin Room, 1 Bedroom, Jetted Tub, City View | View from room

9. 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 NT$2,074
NT$2,502 total
includes taxes & fees
Sep 29 - Sep 30
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"I never write hotel reviews, but this hotel was so exceptional that I had to share my experience. The room was beautiful, spotless, and incredibly comfortable, with thoughtful turn-down service every evening. The staff were truly the most attentive and welcoming I’ve ever experienced. They helped arrange pickup from the train station, made restaurant reservations, and went above and beyond in so many little ways. Those small details made me feel genuinely cared for. The breakfast was lovely and served in such a beautiful setting — the perfect way to start the day. I absolutely loved my stay here and would come back to Cortona for this hotel alone. A truly special place with exceptional hospitality. Highly recommend!"
Turia 3-night trip
Posted 8 hours ago
Monastero di Cortona Hotel & Spa

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 86 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?

Enjoy the area's cultural attractions such as Museo Diocesano, or get outdoors into nature at a spot like Val di Chiana. Tennis Club Castiglionese and Vasari Loggia 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.