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

Castiglion Fiorentino Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Castiglion Fiorentino vacation rentals

A couple relaxing in a spa setting with a visible logo on the wall, a reception desk, and a plant in the background.

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$4,309
NT$4,885 total
includes taxes & fees
Nov 9 - Nov 10
San Michele al Borgo
Pool

2. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (41 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is NT$2,396
NT$2,853 total
includes taxes & fees
Nov 18 - Nov 19
iConic Wellness Resort
A restaurant named 'SALUMERIA FOCACCE E VINI' with outdoor seating and a stone facade.

3. 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 NT$2,465
NT$3,344 total
includes taxes & fees
Nov 2 - Nov 3
Limehome Arezzo Duomo
Room

4. 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 NT$2,958
NT$3,471 total
includes taxes & fees
Nov 1 - Nov 2
Bibi Boutique
A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

5. 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 NT$4,579
NT$5,110 total
includes taxes & fees
Nov 1 - Nov 2
B&B Piccolo Hotel
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

6. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay!"
Canada
Brian
The price is NT$10,956
NT$12,196 total
includes taxes & fees
Nov 15 - Nov 16
Fontelunga Hotel & Villas
A villa with a swimming pool, outdoor seating, and a tennis court.

7. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (83 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
Villa Curina Resort
A view of a historic town with prominent buildings and a church tower.

8. 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 NT$2,904
NT$3,411 total
includes taxes & fees
Nov 5 - Nov 6
Cameracaffè Centro
A modern hotel room with large windows, a bed, a desk, and a chair.

9. B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.2 out of 10, Very good, (84 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$2,443
NT$2,904 total
includes taxes & fees
Nov 8 - Nov 9
B&B 52cento
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

10. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (168 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is NT$4,426
NT$5,086 total
includes taxes & fees
Nov 5 - Nov 6
Hotel San Gregorio
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

11. 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 NT$2,100
NT$2,419 total
includes taxes & fees
Nov 26 - Nov 27
Abbadia Sicille Relais
A crowded restaurant with brick walls and multiple tables and chairs.

12. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is NT$4,930
NT$5,568 total
includes taxes & fees
Nov 25 - Nov 26
La Locanda di San Francesco
A spa area with a stone-walled arch, a hot tub, and a small window.

13. 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 NT$3,560
NT$4,060 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.

14. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.4 out of 10, Exceptional, (48 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 NT$8,899
NT$9,934 total
includes taxes & fees
Nov 1 - Nov 2
Castello di Gargonza
An interior courtyard with stone columns, arches, and a mosaic.

15. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (120 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is NT$5,152
NT$5,812 total
includes taxes & fees
Oct 31 - Nov 1
Meublé Il Riccio
An arched stone gateway leading to a pathway lined with potted plants and lights.

16. Castello di Modanella

Castello di Modanella
Rapolano Terme
8.0 out of 10, Very good, (17 reviews)
"To far out"
United States
Dennis
The price is NT$4,851
NT$6,566 total
includes taxes & fees
Oct 31 - Nov 1
Castello di Modanella
A terrace with a table set for breakfast, overlooking a scenic landscape.

17. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (49 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is NT$5,511
NT$6,207 total
includes taxes & fees
Oct 31 - Nov 1
Delcorto Suites
A poolside area with two glasses of water, candles, and a stone pathway.

18. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (104 reviews)
"The variety at the buffet was really good and the coffee machines made really good coffee. The site itself was very nice and well maintained. The problem with this place is the reception for arrival and departure, no service and fast to dismiss you."
Canada
DANIELA
The price is NT$5,785
NT$6,508 total
includes taxes & fees
Nov 24 - Nov 25
Casanova - Panoramic Rooms and Suites
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

19. 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$2,623
NT$3,030 total
includes taxes & fees
Oct 31 - Nov 1
Artisti del Cavallo Tourism
Exterior

20. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is NT$3,698
NT$4,213 total
includes taxes & fees
Oct 31 - Nov 1
montorio
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castiglion Fiorentino Hotel Reviews

Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"One of the cleanest hotels I’ve ever seen. Very old but beautifully maintained. The bed was a little too hard. It was a lovely property and good value."
Rebecca 1-night trip
Posted 4 hours ago
Hotel Corsignano

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
  • Use the map to find apartments and other holiday homes in the Castiglion Fiorentino neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Castiglion Fiorentino while they last

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.

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.