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
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Castiglion Fiorentino vacation rentals

Exterior

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 SAR 497
SAR 564 total
includes taxes & fees
6 Jul - 7 Jul
San Michele al Borgo
Private kitchen

Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is SAR 345
SAR 439 total
includes taxes & fees
26 Jun - 27 Jun
Happy Nest Tuscany Between Florence and Rome
Spa

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

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 SAR 426
SAR 597 total
includes taxes & fees
3 Jul - 4 Jul
The window on the tower apartment new castiglion fiorentino
Dining

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 SAR 576
SAR 669 total
includes taxes & fees
2 Jul - 3 Jul
Casa Lèon, Relax Nature and Comfort in the Heart of Valdichiana.
Spa

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

Apartment 'Capannina - Borgo Dolci Colline Resort' with Pool, Terrace & Shared Garden
Castiglion Fiorentino
The price is SAR 684
SAR 692 total
includes taxes & fees
26 Jun - 27 Jun
Apartment 'Capannina - Borgo Dolci Colline Resort' with Pool, Terrace & Shared Garden
1 treatment room, massages

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (91 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is SAR 634
SAR 715 total
includes taxes & fees
22 Jul - 23 Jul
Casanova - Panoramic Rooms and Suites
Lobby

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is SAR 593
SAR 652 total
includes taxes & fees
1 Jul - 2 Jul
Villa Cassia di Baccano
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (177 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is SAR 577
SAR 647 total
includes taxes & fees
28 Jun - 29 Jun
Abbadia Sicille Relais
Bar (on property)

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 SAR 453
SAR 507 total
includes taxes & fees
26 Jun - 27 Jun
La Piccola Locanda
Suite, 2 Bedrooms | Courtyard view

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 SAR 2,515
SAR 2,784 total
includes taxes & fees
12 Jul - 13 Jul
L'Olmo
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (34 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
The price is SAR 593
SAR 652 total
includes taxes & fees
10 Jul - 11 Jul
Villa di Sotto
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (148 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is SAR 806
SAR 912 total
includes taxes & fees
22 Jul - 23 Jul
Hotel San Gregorio
Lunch and dinner served

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (42 reviews)
"Beautiful historic fortress / castle with tastefully updated rooms, great amenities that maintains the old character "
Canada
Ariel
The price is SAR 986
SAR 1,102 total
includes taxes & fees
28 Jun - 29 Jun
Castello di Gargonza
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (37 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is SAR 726
SAR 816 total
includes taxes & fees
27 Jun - 28 Jun
Delcorto Suites
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (138 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is SAR 461
SAR 524 total
includes taxes & fees
26 Jun - 27 Jun
Bed & Breakfast Vicolo dell'Oste
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (69 reviews)
"This was our second stay. The property is beautiful and our room was lovely. The breakfast was one of the best on our trip in Italy."
Canada
Dr Anne
The price is SAR 613
SAR 708 total
includes taxes & fees
2 Jul - 3 Jul
Villa Curina Resort
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (111 reviews)
"It was very well located ."
Canada
Marlenne
The price is SAR 607
SAR 685 total
includes taxes & fees
29 Jun - 30 Jun
Meublé Il Riccio
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (144 reviews)
"Great location."
United States
James
The price is SAR 508
SAR 576 total
includes taxes & fees
19 Jul - 20 Jul
La Locanda di San Francesco
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (103 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is SAR 314
SAR 362 total
includes taxes & fees
30 Jun - 1 Jul
Residenza Fabroni
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

Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa

10/10 Excellent
"Absolutamente perfecto. Todo my limpio y nuevo..staff super amable y resolutivo..el desayuno buenísimo y diverso y de gran calidad el hotel me sorprendió... mucho mejor que en las fotos"
Isis 2-night trip
Posted 6 hours ago
Poggio Paradiso Resort & Spa

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?

Lovely home in Castiglion Fiorentino: Visitors give good reviews to this Castiglion Fiorentino vacation home rental, which is located on a lake and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like foosball.

How many vacation rentals are there in Castiglion Fiorentino?

With 74 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. Cassero Tower and Tennis Club Castiglionese 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.