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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Castiglion Fiorentino vacation rentals

Exterior

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 AED 504
AED 571 total
includes taxes & fees
22 Aug - 23 Aug
San Michele al Borgo
Interior

2. 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.
The price is AED 423
AED 592 total
includes taxes & fees
6 Aug - 7 Aug
The window on the tower apartment new castiglion fiorentino
Private kitchen

3. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is AED 211
AED 304 total
includes taxes & fees
1 Sep - 2 Sep
Happy Nest Tuscany Between Florence and Rome
Dining

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

Casa Lèon, Relax Nature and Comfort in the Heart of Valdichiana.
Toscana
The price is AED 571
AED 668 total
includes taxes & fees
6 Aug - 7 Aug
Casa Lèon, Relax Nature and Comfort in the Heart of Valdichiana.
Outdoor dining

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

Apartment 'Granaio - Borgo Dolci Colline' with Private Pool, Wi-Fi, and Air Conditioning
Castiglion Fiorentino
The price is AED 3,060
AED 3,069 total
includes taxes & fees
2 Sep - 3 Sep
Apartment 'Granaio - Borgo Dolci Colline' with Private Pool, Wi-Fi, and Air Conditioning
Property grounds

6. Dimora del Poggio - cozy Tuscan apartment

Dimora del Poggio - cozy Tuscan apartment
San Quirico d'Orcia
10.0 out of 10, Exceptional, (5 reviews)
"Our hosts were fantastic, the apartment was clean, roomy, and comfortable, and the location was perfect. Easy walk to enjoy shops and dining."
United States
Joe B.
The price is AED 545
AED 761 total
includes taxes & fees
3 Sep - 4 Sep
Dimora del Poggio - cozy Tuscan apartment
Couples treatment rooms, sauna, hot tub, steam room, body treatments

7. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (49 reviews)
"Our stay was great. "
United States
Elena
The price is AED 366
AED 419 total
includes taxes & fees
6 Aug - 7 Aug
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Exterior

8. SUITE WINE - Relax & Design in the Heart of the Valdorcia

SUITE WINE - Relax & Design in the Heart of the Valdorcia
San Quirico d'Orcia
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful, clean, comfortable apartment in a great location."
United Kingdom
priscilla e.
The price is AED 380
AED 579 total
includes taxes & fees
2 Sep - 3 Sep
SUITE WINE - Relax & Design in the Heart of the Valdorcia
1 treatment room, massages

9. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (93 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is AED 618
AED 697 total
includes taxes & fees
31 Aug - 1 Sep
Casanova - Panoramic Rooms and Suites
Suite, 2 Bedrooms | Courtyard view

10. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is AED 2,663
AED 2,946 total
includes taxes & fees
17 Aug - 18 Aug
L'Olmo
Bar (on property)

11. La Piccola Locanda

La Piccola Locanda
Chiusi
7.8 out of 10, Good, (11 reviews)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
The price is AED 436
AED 489 total
includes taxes & fees
5 Sep - 6 Sep
La Piccola Locanda
Interior

12. Boutique Apartment Eleganza

Boutique Apartment Eleganza
Chiusi Scalo
9.6 out of 10, Exceptional, (5 reviews)
"Amazing apartment!So close to the train!"
United States
Ryan W.
The price is AED 397
AED 485 total
includes taxes & fees
12 Aug - 13 Aug
Boutique Apartment Eleganza
Outdoor dining

13. Suite Gioconda - Podere Casa Rossa in Pienza

Suite Gioconda - Podere Casa Rossa in Pienza
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Comfortable, clean and the hosts are over the top welcoming! Walking distance to Pienza with gorgeous views. Loved staying here and hope to come back someday! "
United States
Doug H.
The price is AED 829
AED 1,058 total
includes taxes & fees
16 Aug - 17 Aug
Suite Gioconda - Podere Casa Rossa in Pienza
Exterior

14. Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Good communication with management through WhatsApp. The taxi dropped us off one minute from the property. Very cozy top floor with only a few steps. The 2 bedroom unit is very comfortable, the kids enjoyed sleeping in the loft. Air conditioning worked very well. We had everything we needed, the location is wonderful. We really enjoyed our stay. Thank you!"
United States
Nancy
The price is AED 477
AED 541 total
includes taxes & fees
31 Aug - 1 Sep
Casa Gioia - Casa Olivieri
Monolocale Exclusive, vista città, secondo piano senza ascensore | Laptop workspace, iron/ironing board, WiFi (free)

15. TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is AED 381
AED 436 total
includes taxes & fees
6 Aug - 7 Aug
TuscanyLettings Studio&Room
Exterior detail

16. Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi

Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Pienza
The price is AED 629
AED 731 total
includes taxes & fees
10 Aug - 11 Aug
Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio

17. PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (5 reviews)
"Clean room with friendly and helpful staff. Thank you so much for the wonderful stay"
United States
Pearlyn
The price is AED 418
AED 477 total
includes taxes & fees
25 Aug - 26 Aug
PienzaLettings Suites
Food and drink

18. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (152 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is AED 683
AED 777 total
includes taxes & fees
6 Aug - 7 Aug
Hotel San Gregorio
2 bedrooms, desk, iron/ironing board, travel crib

19. The house in the village - Angelica apartment - Vald'Orcia

The house in the village - Angelica apartment - Vald'Orcia
Monticchiello
10.0 out of 10, Exceptional, (12 reviews)
"Marco was great to work with, was easily available for any of our questions and the stay was wonderful. The apartment is in a great location and had all we needed for our stay."
United States
Melissa B.
The price is AED 444
AED 537 total
includes taxes & fees
24 Aug - 25 Aug
The house in the village - Angelica apartment - Vald'Orcia
Coffee/tea maker, fridge, microwave, stovetop

20. "Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (11 reviews)
"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "
Australia
Dan
The price is AED 423
AED 516 total
includes taxes & fees
19 Aug - 20 Aug
"Il Focolare" Superior Apartment in Monticchiello
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

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

10/10 Excellent
"The place it’s an Amazing. Very clean. Is more beautiful than the pictures."
Ervin 1-night trip
Posted 3 days ago
Precise Tale Poggio Alla Sala

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?

La Dolce Collina: You might like this vacation home rental near Castiglion Fiorentino. It is located in a rural location and has a garden, a hot tub, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and kitchenware.

How many vacation rentals are there in Castiglion Fiorentino?

With 82 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?

Cultural attractions include Municipal Art Gallery, whereas Val di Chiana is a spot to enjoy nature. Vasari Loggia and Archaeological Museum 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.