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 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

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 ￥21,397
￥24,263 total
includes taxes & fees
Aug 4 - Aug 5
San Michele al Borgo
Interior

2. The window on the tower apartment new castiglion fiorentino

The window on the tower apartment new castiglion fiorentino
Castiglion fiorentino
10.0 out of 10, Exceptional, (1 review)
"Large apartment 4 floors above the town. Easy walking to anywhere in the area. Great shower and large bathroom. Equipped kitchen with big refrigerator. Living room with TV and dining table and couch. Large bedroom with fan. Also, there is a hairdryer and ironing board and iron. You are very close to walk to restaurants and stores, About a mile from the train station up a hill but the hostess helped us with transport.Overall, an excellent stay for my wife and I. (Be aware the room is 4...
United States
aric w.
The price is ￥18,144
￥25,402 total
includes taxes & fees
Aug 2 - Aug 3
The window on the tower apartment new castiglion fiorentino
Private kitchen

3. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is ￥9,072
￥13,064 total
includes taxes & fees
Sep 1 - Sep 2
Happy Nest Tuscany Between Florence and Rome
Dining

4. Casa Lèon, Relax Nature and Comfort in the Heart of Valdichiana.

Casa Lèon, Relax Nature and Comfort in the Heart of Valdichiana.
Toscana
The price is ￥24,495
￥28,668 total
includes taxes & fees
Aug 5 - Aug 6
Casa Lèon, Relax Nature and Comfort in the Heart of Valdichiana.
Outdoor dining

5. Apartment 'Granaio - Borgo Dolci Colline' with Private Pool, Wi-Fi, and Air Conditioning

Apartment 'Granaio - Borgo Dolci Colline' with Private Pool, Wi-Fi, and Air Conditioning
Castiglion Fiorentino
The price is ￥131,363
￥131,726 total
includes taxes & fees
Sep 1 - Sep 2
Apartment 'Granaio - Borgo Dolci Colline' with Private Pool, Wi-Fi, and Air Conditioning
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

6. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (38 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is ￥18,557
￥21,501 total
includes taxes & fees
Aug 2 - Aug 3
iConic Wellness Resort
Outdoor dining

7. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is ￥13,993
￥19,444 total
includes taxes & fees
Aug 5 - Aug 6
Dolce Casa 2 by Tiny Away
1 bedroom, WiFi, bed sheets

8. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
The price is ￥15,026
￥20,477 total
includes taxes & fees
Aug 5 - Aug 6
Dolce Casa 1 by Tiny Away
Apartment (1 Bedroom) | Front of property

9. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is ￥15,708
￥18,005 total
includes taxes & fees
Aug 3 - Aug 4
Vicolo Della Scala Rooms - La Luna
Porch

10. 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 ￥13,202
￥15,612 total
includes taxes & fees
Aug 4 - Aug 5
Cameracaffè Centro
Courtyard

11. 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 ￥48,944
￥54,564 total
includes taxes & fees
Aug 9 - Aug 10
Fontelunga Hotel & Villas
Lobby

12. 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 ￥23,603
￥26,690 total
includes taxes & fees
Aug 2 - Aug 3
B&B Piccolo Hotel
Property grounds

13. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
10.0 out of 10, Exceptional, (8 reviews)
"This place was such a great find! So central and easily reachable. We really enjoyed our stay!"
United States
Julie R.
The price is ￥16,965
￥17,691 total
includes taxes & fees
Aug 4 - Aug 5
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

14. 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 ￥18,799
￥21,405 total
includes taxes & fees
Aug 2 - Aug 3
DormiVeglia B&B
Outdoor dining

15. Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is ￥11,431
￥14,697 total
includes taxes & fees
Aug 30 - Aug 31
Holiday home with panoramic terrace ideal for families and couples
Exterior

16. Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
The price is ￥12,973
￥25,674 total
includes taxes & fees
Aug 11 - Aug 12
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Interior

17. La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
9.8 out of 10, Exceptional, (38 reviews)
"This was perfectly clean. The host was perfect."
United States
Michelle H.
The price is ￥23,678
￥36,016 total
includes taxes & fees
Aug 3 - Aug 4
La Finestra sul Teatro
Luxury Double or Twin Room, 1 Bedroom, Jetted Tub, City View | View from room

18. 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 ￥12,945
￥15,328 total
includes taxes & fees
Aug 24 - Aug 25
B&B 52cento
Interior

19. Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Shabby Chic House<br>(Independent & balcony)
Cortona Old Town
10.0 out of 10, Exceptional, (3 reviews)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is ￥22,728
￥26,593 total
includes taxes & fees
Aug 2 - Aug 3
Cortona Shabby Chic House<br>(Independent & balcony)
Exterior

20. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very Good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is ￥12,635
￥14,625 total
includes taxes & fees
Aug 3 - Aug 4
Artisti del Cavallo Tourism
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

Hotel Villa Ricci

Hotel Villa Ricci

10/10 Excellent
"The staff was so incredibly friendly and accommodating. They were ready with recommendations, patient with our lack of Italian knowledge, and always smiling when we entered. The spa is so lovely and relaxing, and reasonably priced. Breakfast spread is lovely and served fairly late into the morning. Walkable to multiple delicious restaurants nearby. We would definitely recommend this hotel if you’re visiting Tuscany."
Amber 2-night trip
Posted 18 hours ago
Hotel Villa Ricci

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

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?

La Dolce Collina: You might like this vacation home rental near Castiglion Fiorentino. It is located in a rural location and has a garden, a hot tub, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and kitchenware.

How many vacation rentals are there in Castiglion Fiorentino?

With 82 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. Vasari Loggia and Archaeological Museum 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.