Castiglion Fiorentino Vacation Rentals from AED 255: Search Short-Term Rentals

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

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Our top choices for Castiglion Fiorentino vacation rentals

A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

1. San Michele al Borgo

Castiglion Fiorentino

Vern

AED 547 total

includes taxes & fees

15 Nov - 16 Nov

A wooden door with a metal handle and a small decorative figure.

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.

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

Toscana

AED 676 total

includes taxes & fees

12 Dec - 13 Dec

A villa with a swimming pool, surrounded by lush greenery and hills.

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

Castiglion Fiorentino

AED 611 total

includes taxes & fees

16 Nov - 17 Nov

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a clear sky.

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

Castiglion Fiorentino

AED 2,760 total

includes taxes & fees

8 Dec - 9 Dec

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

6. Arc two-bedroom apartment

Cortona

AED 1,109 total

includes taxes & fees

15 Nov - 16 Nov

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

Castiglion Fiorentino

AED 534 total

includes taxes & fees

16 Nov - 17 Nov

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

Castiglion Fiorentino

AED 1,324 total

includes taxes & fees

21 Nov - 22 Nov

A two-story house with a stone facade, a tiled roof, and a small garden area with potted plants.

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

Toscana

AED 1,696 total

includes taxes & fees

16 Nov - 17 Nov

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

AED 1,656 total

includes taxes & fees

16 Nov - 17 Nov

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

AED 1,696 total

includes taxes & fees

16 Nov - 17 Nov

12. iConic Wellness Resort

Arezzo

Wade

AED 329 total

includes taxes & fees

16 Nov - 17 Nov

A bedroom with a bed, a bedside table, a mirror, and windows with curtains.

13. Limehome Arezzo Duomo

Arezzo Centro Storico

Florian

AED 383 total

includes taxes & fees

30 Nov - 1 Dec

A person sitting on a wooden chair in a garden with a table and chairs in the background.

14. Dolce Casa 2 by Tiny Away

Rigutino

AED 396 total

includes taxes & fees

16 Nov - 17 Nov

An outdoor patio with a white candelabra, a table with a vase of flowers, and a chair.

15. Bibi Boutique

Arezzo Centro Storico

Carol

AED 345 total

includes taxes & fees

15 Dec - 16 Dec

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

AED 481 total

includes taxes & fees

16 Nov - 17 Nov

A house number 102, a security keypad, and a plaque with a floral design.

17. Vacation home with a panoramic terrace, ideal for families and couples

Cortona

AED 300 total

includes taxes & fees

15 Nov - 16 Nov

A stone building with a green door, a window with shutters, and a small window with bars.

18. CASA AMBRA

Cortona Old Town

AED 826 total

includes taxes & fees

15 Nov - 16 Nov

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

19. Cameracaffè Centro

Arezzo Centro Storico

Alexandre

AED 405 total

includes taxes & fees

16 Nov - 17 Nov

A dining area with a wooden table, chairs, and a mirror. There is a clock on the wall and a window with a view.

20. Cortona Shabby Chic House<br>(Detached & Balcony)

Cortona Old Town

Erin

AED 557 total

includes taxes & fees

15 Nov - 16 Nov

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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

A bathroom with a white sink, a towel rack, and a wooden floor.

La Cantina Relais - Fattoria Il Cipresso

Arezzo

10/10 Excellent

Steve

A terrace with stone steps, outdoor furniture, and a tree planter.

San Michele al Castello

Castiglion Fiorentino

10/10 Excellent

Edward

A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.

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

An outdoor seating area with tables and chairs, potted plants, and a view of the sea.

Villa Santa Margherita

Cortona Old Town

10/10 Excellent

THUHUONG

A historic town with traditional architecture, a central courtyard with a swimming pool, and a view of distant mountains.

Monastero di Cortona Hotel & Spa

Cortona Old Town

10/10 Excellent

Eric

Terra Antica Resort

Montepulciano

10/10 Excellent

Nikhil

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

A garden pathway leading to a building with a yellow facade and arched windows.

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

An arched entrance with a wooden balcony, a tiled floor, and a door leading inside.

Hotel Boutique Castiglione del Lago

Contrada Castello

10/10 Excellent

Anonymous traveler

An aerial view of a property with a swimming pool, two buildings, and vineyard rows.

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...

An aerial view of a rural estate with a large building, a swimming pool, and well-maintained gardens.

Podere San Giuseppe

Castiglione del Lago

10/10 Excellent

Timothy

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

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

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

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

6. Arc two-bedroom apartment

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

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. Limehome Arezzo Duomo

14. Dolce Casa 2 by Tiny Away

15. Bibi Boutique

16. DormiVeglia B&B

17. Vacation home with a panoramic terrace, ideal for families and couples

18. CASA AMBRA

19. Cameracaffè Centro

20. Cortona Shabby Chic House<br>(Detached & Balcony)

Find vacation rentals that suit your style

Top Castiglion Fiorentino Hotel Reviews

Bed & Breakfast Viziottavo

10/10 Excellent

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?