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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Castiglion Fiorentino vacation rentals

A breakfast setting with a fireplace, a table with plates, glasses, and a croissant.

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 ￥21,063
￥23,876 total
includes taxes & fees
Nov 8 - Nov 9
San Michele al Borgo
A window with a view of a historic town, including a prominent tower and colorful buildings.

2. "La fenêtre sur la tour" New Apartment in Castiglion Fiorentino

"La fenêtre sur la tour" New Apartment in 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 ￥17,673
￥23,505 total
includes taxes & fees
Nov 6 - Nov 7
"La fenêtre sur la tour" New Apartment in Castiglion Fiorentino
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a clear sky.

3. Holiday Home 'Casa Dei Girasoli' with Private Pool, Wi-Fi and Air Conditioning

Holiday Home 'Casa Dei Girasoli' with Private Pool, Wi-Fi and Air Conditioning
Castiglion Fiorentino
The price is ￥91,616
￥120,777 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Home 'Casa Dei Girasoli' with Private Pool, Wi-Fi and Air Conditioning
A kitchen with wooden cabinets, a tiled backsplash, a stove, and a dining area with a table and chairs.

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

Casa Lèon: Relaxation, Nature, and Comfort in the Heart of Valdichiana.
Toscana
The price is ￥23,858
￥25,449 total
includes taxes & fees
Nov 6 - Nov 7
Casa Lèon: Relaxation, Nature, and Comfort in the Heart of Valdichiana.
An outdoor dining area with a table set for two, string lights, and a view of trees and hills.

5. Capannina - Borgo Dolci Colline Resort Apartment with Pool, Terrace & Shared Garden

Capannina - Borgo Dolci Colline Resort Apartment with Pool, Terrace & Shared Garden
Castiglion Fiorentino
The price is ￥22,975
￥23,328 total
includes taxes & fees
Nov 17 - Nov 18
Capannina - Borgo Dolci Colline Resort Apartment with Pool, Terrace & Shared Garden
A patio area with a table and chairs, a wooden pergola, and a view of a kitchen.

6. Arc two-bedroom apartment

Arc two-bedroom apartment
Cortona
The price is ￥40,648
￥48,424 total
includes taxes & fees
Nov 14 - Nov 15
Arc two-bedroom apartment
An outdoor dining area with a table set for two, string lights, and a view of trees and hills.

7. Cipresso Apartment at Borgo Dolci Colline Resort with Shared Pool, Wi-Fi & Air Conditioning

Cipresso Apartment at Borgo Dolci Colline Resort with Shared Pool, Wi-Fi & Air Conditioning
Castiglion Fiorentino
The price is ￥26,333
￥26,686 total
includes taxes & fees
Nov 5 - Nov 6
Cipresso Apartment at Borgo Dolci Colline Resort with Shared Pool, Wi-Fi & Air Conditioning
An outdoor dining area with a table set for two, string lights, and a view of trees and hills.

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

Apartment 'Granaio - Borgo Dolci Colline' with Private Pool, Wi-Fi & Air Conditioning
Castiglion Fiorentino
The price is ￥54,786
￥55,139 total
includes taxes & fees
Nov 17 - Nov 18
Apartment 'Granaio - Borgo Dolci Colline' with Private Pool, Wi-Fi & Air Conditioning
A bedroom with a bed, a nightstand, a dresser, a window with curtains, and a wooden ceiling.

9. Pheasant swimming pool flat with 3 bedrooms and two bathrooms

Pheasant swimming pool flat with 3 bedrooms and two bathrooms
Toscana
The price is ￥60,972
￥74,050 total
includes taxes & fees
Nov 17 - Nov 18
Pheasant swimming pool flat with 3 bedrooms and two bathrooms
An outdoor patio with a table and chairs, a stone wall, and a door.

10. Tobacconist's flat on two floors consisting of 3 bedrooms and two bathrooms

Tobacconist's flat on two floors consisting of 3 bedrooms and two bathrooms
Toscana
The price is ￥60,972
￥72,283 total
includes taxes & fees
Nov 17 - Nov 18
Tobacconist's flat on two floors consisting of 3 bedrooms and two bathrooms
A cozy kitchen with wooden beams, a dining table with chairs, a fireplace, and a television.

11. La Lepre swimming pool flat with 3 bedrooms and two bathrooms

La Lepre swimming pool flat with 3 bedrooms and two bathrooms
Toscana
The price is ￥60,972
￥74,050 total
includes taxes & fees
Nov 17 - Nov 18
La Lepre swimming pool flat with 3 bedrooms and two bathrooms
Pool

12. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (43 reviews)
"It was wonderful!"
United States
Wade
The price is ￥11,713
￥13,945 total
includes taxes & fees
Dec 2 - Dec 3
iConic Wellness Resort
A bedroom with a bed, a desk, a chair, and a staircase.

13. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.4 out of 10, Exceptional, (26 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is ￥22,384
￥24,975 total
includes taxes & fees
Nov 5 - Nov 6
B&B Piccolo Hotel
A hotel room with a bed, a desk with a chair, a wardrobe, a television, and a window with curtains.

14. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
9.2 out of 10, Wonderful, (5 reviews)
"I really liked the brand new room. Nice design and super comfy bed. Plus free coffee is a nice addition to the experience there. Loved it. Plus my personal highlight were the nice views into the historical center of Arezzo."
Germany
Florian
The price is ￥10,070
￥14,186 total
includes taxes & fees
Nov 9 - Nov 10
Limehome Arezzo Duomo
A bedroom with a large bed, a chandelier, a mirror, and plants.

15. Bibi Boutique

Bibi Boutique
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
"The BiBi was perfect for my needs. Its location is excellent, and the room had all the needed amenities. Fabio was a gracious host, orienting me to Arezzo and recommending a wonderful trattoria close by. I highly recommend and hope to return!"
United States
Carol
The price is ￥12,580
￥14,898 total
includes taxes & fees
Nov 6 - Nov 7
Bibi Boutique
An outdoor dining setup with a pool and lounge chairs in the background.

16. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (30 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is ￥16,963
￥19,369 total
includes taxes & fees
Nov 9 - Nov 10
DormiVeglia B&B
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

17. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.4 out of 10, Exceptional, (49 reviews)
"Roberto, his wife and his staff were all round great. Very friendly helpful and great service. We were very happy to find this authentic castle/village to stay in Tuscany."
Canada
Iain
The price is ￥43,500
￥48,557 total
includes taxes & fees
Nov 6 - Nov 7
Castello di Gargonza
A balcony with potted plants and a view of a cityscape.

18. Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (195 reviews)
"Pros: Nice staff. Good breakfast with a nice view. Cons: Old bed and can feel the metal springs in your back so poor sleep. Lots of beggars and vagrants at the entrance of building."
United States
Steven
The price is ￥14,195
￥16,674 total
includes taxes & fees
Nov 7 - Nov 8
Cameracaffè Centro
A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

19. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
The price is ￥11,936
￥17,235 total
includes taxes & fees
Nov 5 - Nov 6
Dolce Casa 2 by Tiny Away
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

20. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
The price is ￥10,266
￥11,823 total
includes taxes & fees
Dec 2 - Dec 3
Abbadia Sicille Relais
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 San Gregorio

Hotel San Gregorio

10/10 Excellent
"Great place to stay. Perfect location. Wonderful breakfast. Nice room. Underground parking could be a bit nicer, but they are actively working on it. Great place."
JOHN PAUL 2-night trip
Posted 1 day ago
Hotel San Gregorio

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:

  • View our selection of featured holiday rentals in Castiglion Fiorentino
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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?

Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!: This vacation home rental near Castiglion Fiorentino is located in a rural location and has an outdoor pool, a patio, and air-conditioning to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Castiglion Fiorentino?

With 85 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.