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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
$124 nightly
The price is $141
Oct 19 - Oct 20
Total with taxes and fees
San Michele al Borgo
A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

2. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
$71 nightly
The price is $75
Oct 8 - Oct 9
Total with taxes and fees
Happy Nest Tuscany Between Florence and Rome
A window with a view of a historic town, including a prominent tower and colorful buildings.

3. 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.
$155 nightly
The price is $157
Oct 8 - Oct 9
Total with taxes and fees
The window on the tower apartment new castiglion fiorentino
An outdoor dining area with a table set for two, string lights, and a view of trees and hills.

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

Capannina - Borgo Dolci Colline Resort Apartment with Pool, Terrace & Shared Garden
Castiglion Fiorentino
$146 nightly
The price is $148
Oct 8 - Oct 9
Total with taxes and fees
Capannina - Borgo Dolci Colline Resort Apartment with Pool, Terrace & Shared Garden
An outdoor dining area with a table set for two, string lights, and a view of trees and hills.

5. 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
$196 nightly
The price is $199
Oct 12 - Oct 13
Total with taxes and fees
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.

6. 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
$348 nightly
The price is $350
Oct 8 - Oct 9
Total with taxes and fees
Apartment 'Granaio - Borgo Dolci Colline' with Private Pool, Wi-Fi & Air Conditioning
Pool

7. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (40 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
$74 nightly
The price is $89
Oct 25 - Oct 26
Total with taxes and fees
iConic Wellness Resort
A compact kitchen with wooden cabinets, a black microwave, and a countertop with a sink.

8. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
10.0 out of 10, Exceptional, (3 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
$74 nightly
The price is $81
Oct 12 - Oct 13
Total with taxes and fees
Limehome Arezzo Duomo
A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

9. Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Rigutino
$120 nightly
The price is $120
Oct 8 - Oct 9
Total with taxes and fees
Dolce Casa 2 by Tiny Away
Room

10. Bibi Boutique

Bibi Boutique
Arezzo Centro Storico
$73 nightly
The price is $87
Oct 14 - Oct 15
Total with taxes and fees
Bibi Boutique
An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

11. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
$142 nightly
The price is $159
Nov 2 - Nov 3
Total with taxes and fees
B&B Piccolo Hotel
A spa area with a stone-walled arch, a hot tub, and a small window.

12. 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
$109 nightly
The price is $124
Oct 11 - Oct 12
Total with taxes and fees
DormiVeglia B&B
Room

13. Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Rigutino
$127 nightly
The price is $127
Oct 8 - Oct 9
Total with taxes and fees
Dolce Casa 1 by Tiny Away
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

14. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay!"
Canada
Brian
$243 nightly
The price is $272
Oct 12 - Oct 13
Total with taxes and fees
Fontelunga Hotel & Villas
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

15. 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
$81 nightly
The price is $93
Oct 13 - Oct 14
Total with taxes and fees
Artisti del Cavallo Tourism
A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

16. 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)
"Beautiful location. Can't wait to go back."
United States
Dawn H.
$105 nightly
The price is $109
Oct 8 - Oct 9
Total with taxes and fees
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
A narrow street with buildings on either side, stone walls, and a clear blue sky.

17. 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
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
A view of a historic town with prominent buildings and a church tower.

18. Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (194 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
$83 nightly
The price is $98
Oct 15 - Oct 16
Total with taxes and fees
Cameracaffè Centro
A park with picnic tables, a playground, and a gravel path.

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

Holiday home with panoramic terrace ideal for families and couples
Cortona
$91 nightly
The price is $91
Oct 8 - Oct 9
Total with taxes and fees
Holiday home with panoramic terrace ideal for families and couples
An arched stone bridge with a white building on the right, featuring a balcony with plants.

20. Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (20 reviews)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
$100 nightly
The price is $110
Oct 18 - Oct 19
Total with taxes and fees
Locanda Antico Borgo
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Beautiful experience. Would recommend again and again."
MICHELLE 3-night trip
Posted 13 hours ago
Monastero di Cortona Hotel & Spa

Find out more about Castiglion Fiorentino

Everything you need to know about Castiglion Fiorentino vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Castiglion Fiorentino vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castiglion Fiorentino vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castiglion Fiorentino vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castiglion Fiorentino. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Castiglion Fiorentino in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $63 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Castiglion Fiorentino rentals

At Expedia, we put the best Castiglion Fiorentino vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Castiglion Fiorentino rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castiglion Fiorentino vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castiglion Fiorentino. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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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.