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

Castiglion Fiorentino Vacation Rentals

Where to?

Dates

November 2026

December 2026

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

In two months

In three months

In four months

Our top choices for Castiglion Fiorentino vacation rentals

1. San Michele al Borgo

Castiglion Fiorentino

Vern

￥23,876 total

includes taxes & fees

Nov 12 - Nov 13

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

Castiglion fiorentino

"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...

aric w.

￥23,623 total

includes taxes & fees

Nov 5 - Nov 6

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

Castiglion Fiorentino

￥120,777 total

includes taxes & fees

Nov 30 - Dec 1

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.

Toscana

￥26,820 total

includes taxes & fees

Nov 5 - Nov 6

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

Castiglion Fiorentino

￥23,446 total

includes taxes & fees

Nov 5 - Nov 6

A patio area with a table and chairs, a wooden pergola, and a view of a kitchen.

6. Arc two-bedroom apartment

Cortona

￥48,424 total

includes taxes & fees

Nov 14 - Nov 15

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

Castiglion Fiorentino

￥26,686 total

includes taxes & fees

Nov 5 - Nov 6

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

Castiglion Fiorentino

￥55,417 total

includes taxes & fees

Nov 5 - Nov 6

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

Toscana

￥74,422 total

includes taxes & fees

Nov 14 - Nov 15

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

Toscana

￥72,646 total

includes taxes & fees

Nov 14 - Nov 15

A pool area with lounge chairs, umbrellas, and a stone building with a tiled roof.

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

Toscana

￥74,422 total

includes taxes & fees

Nov 16 - Nov 17

12. iConic Wellness Resort

Arezzo

Wade

￥13,945 total

includes taxes & fees

Dec 2 - Dec 3

A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

13. B&B Piccolo Hotel

Cortona Old Town

mansoor

￥24,975 total

includes taxes & fees

Nov 6 - Nov 7

A restaurant named 'SALUMERIA FOCACCE E VINI' with outdoor seating and a stone facade.

14. Limehome Arezzo Duomo

Arezzo Centro Storico

Florian

￥14,186 total

includes taxes & fees

Nov 9 - Nov 10

A bedroom with a large bed, a chandelier, a mirror, and plants.

15. Bibi Boutique

Arezzo Centro Storico

Carol

￥14,974 total

includes taxes & fees

Nov 10 - Nov 11

A spa area with a stone-walled arch, a hot tub, and a small window.

16. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

￥19,369 total

includes taxes & fees

Nov 9 - Nov 10

A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

17. Castello di Gargonza

Monte San Savino

Iain

￥48,556 total

includes taxes & fees

Dec 4 - Dec 5

A view of a historic town with prominent buildings and a church tower.

18. Cameracaffè Centro

Arezzo Centro Storico

Steven

￥16,674 total

includes taxes & fees

Nov 7 - Nov 8

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

Rigutino

￥17,443 total

includes taxes & fees

Nov 8 - Nov 9

A covered corridor with brick columns, potted plants, and a view of a lush landscape.

20. Abbadia Sicille Relais

Trequanda

Robert

￥11,823 total

includes taxes & fees

Dec 2 - Dec 3

View all properties

Find vacation rentals that suit your style

Top Castiglion Fiorentino Hotel Reviews

A breakfast buffet with various food items and beverages.

Bed & Breakfast Viziottavo

Castiglion Fiorentino

10/10 Excellent

Anonymous traveler

An outdoor event with people seated at tables, surrounded by stone buildings and greenery.

San Michele al Castello

Castiglion Fiorentino

10/10 Excellent

Edward

A restaurant with glass walls, tables set with white tablecloths, and chairs.

La Cantina Relais - Fattoria Il Cipresso

Arezzo

10/10 Excellent

Steve

A room with a glass floor, stone walls, and a door in the center.

SUGAR ROOMS Residenza d' Epoca

Arezzo Centro Storico

10/10 Excellent

Patricia

A person in a white robe standing by a window with a view of mountains.

Locanda agli Amici

Cortona

10/10 Excellent

This was the perfect away from the city stay for us. Cortona was just a quick few day stay for us but the staff/sylvia were fantastic. Room was clean, the breakfast was delicious. A/c and water pressure from the shower was much needed and the location was perfect for us. It is a short walk from downtown Cortona (steep walk into the city and about 15 mins) but the views are unmatched. Sylvia went above and beyond for us picking us up and dropping us off at the bus station. Highly recommend to...

Kaylan

A terrace with sun loungers, stone walls, and potted plants.

Monastero di Cortona Hotel & Spa

Cortona Old Town

10/10 Excellent

Eric

Terra Antica Resort

Montepulciano

10/10 Excellent

Nikhil

A large estate with multiple buildings, a well-maintained garden, and a vineyard in the background.

Lupaia

Torrita di Siena

10/10 Excellent

This was the most amazing place to stay! This was our favorite stop on a 30-day trip to Greece, Italy and Switzerland. The surrounding countryside is stunning. Our room had a Turkish Bath - what a fun experience. We were a couple of weeks in to our vacation, and we were ready for some down time. Having a private little garden, overlooking the Tuscan hillside was WONDERFUL. The dinner we had on site was one of the best of our entire trip. Breakfast in the morning was an incredible display...

KC Traveler

A hot tub with two glasses of white wine and a plate of strawberries and roses.

Residenza Dei Ricci Relais

Chiusi

10/10 Excellent

My husband and I spent one night at Residenza dei Ricci last weekend and cannot wait to return. It is ideally situated for exploring Chiusi and the surrounding area. Our short time spent under the care of Donatella and Raffaele was one of the best travel experiences we have ever had. They are talented, congenial and generous hosts. The residenza is beautifully appointed with all the amenities one would expect at a luxury hotel -- combined with all the warmth one feels while staying at the home...

Tim

A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

L'Olmo

Pienza

10/10 Excellent

Michelle

A stone building with outdoor seating and a pool in the background.

B&B Country House Poggio del Drago

Civitella in Val di Chiana

10/10 Excellent

Kristen

An aerial view of a vineyard estate with rows of grapevines, a swimming pool, and a red building.

Podere La Rocca

Montepulciano

10/10 Excellent

Our stay at Podere La Rocca was fabulous! The property is located in the rolling Tuscan hills just outside Montepulciano. The property is a working farm and vineyard with an onsite restaurant and pool. Our room was comfortable and clean. The bathroom was huge with a new jetted tub. We stayed on the second floor in a building with a large communal room with a fireplace. On the first floor of the same building was a rec room with a pool table. What made the stay was our experience at the...

A pool surrounded by lavender and yellow flowers, with a stone wall and a building in the background.

Podere San Giuseppe

Castiglione del Lago

10/10 Excellent

Timothy

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.

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.

Castiglion Fiorentino Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Castiglion Fiorentino vacation rentals

1. San Michele al Borgo

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

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

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

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

6. Arc two-bedroom apartment

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

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

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

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

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

12. iConic Wellness Resort

13. B&B Piccolo Hotel

14. Limehome Arezzo Duomo

15. Bibi Boutique

16. DormiVeglia B&B

17. Castello di Gargonza

18. Cameracaffè Centro

19. Dolce Casa 2 by Tiny Away

20. Abbadia Sicille Relais

Find vacation rentals that suit your style

Top Castiglion Fiorentino Hotel Reviews

Bed & Breakfast Viziottavo

10/10 Excellent

Find out more about Castiglion Fiorentino

Frequently Asked Questions

Are there vacation rentals in Castiglion Fiorentino?

What are some of the best vacation rentals that Castiglion Fiorentino has to offer?

How many vacation rentals are there in Castiglion Fiorentino?

What can I see and do in Castiglion Fiorentino?

What are vacation rentals like in Castiglion Fiorentino?