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
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Castiglion Fiorentino vacation rentals

Private kitchen

Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is AED 341
AED 434 total
includes taxes & fees
22 Jun - 23 Jun
Happy Nest Tuscany Between Florence and Rome
Hair dryer, bidet, towels, soap

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

Casa Lèon, Relax Nature and Comfort in the Heart of Valdichiana.
Toscana
Casa Lèon, Relax Nature and Comfort in the Heart of Valdichiana.
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 AED 421
AED 590 total
includes taxes & fees
22 Jun - 23 Jun
The window on the tower apartment new castiglion fiorentino
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 AED 492
AED 558 total
includes taxes & fees
22 Jun - 23 Jun
San Michele al Borgo
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
Apartment 'Capannina - Borgo Dolci Colline Resort' with Pool, Terrace & Shared Garden
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
The price is AED 2,654
AED 2,663 total
includes taxes & fees
25 Jun - 26 Jun
Apartment 'Granaio - Borgo Dolci Colline' with Private Pool, Wi-Fi, and Air Conditioning
Outdoor dining

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
The price is AED 265
AED 341 total
includes taxes & fees
23 Jun - 24 Jun
Holiday home with panoramic terrace ideal for families and couples
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 AED 509
AED 560 total
includes taxes & fees
23 Jun - 24 Jun
Villa Cassia di Baccano
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (33 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 AED 586
AED 645 total
includes taxes & fees
5 Jul - 6 Jul
Villa di Sotto
Front of property

RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.6 out of 10, Exceptional, (7 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is AED 295
AED 345 total
includes taxes & fees
29 Jun - 30 Jun
RESIDENCE LECCIO
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 AED 609
AED 687 total
includes taxes & fees
25 Jun - 26 Jun
Casanova - Panoramic Rooms and Suites
Suite, Multiple Beds, Valley View | Bathroom | Shower, rainfall showerhead, designer toiletries, hair dryer

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 AED 516
AED 584 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 AED 326
AED 375 total
includes taxes & fees
13 Jul - 14 Jul
Residenza Fabroni
Exterior

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
The price is AED 338
AED 633 total
includes taxes & fees
22 Jun - 23 Jun
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (37 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is AED 431
AED 499 total
includes taxes & fees
22 Jun - 23 Jun
iConic Wellness Resort
Outdoor pool

Villa Graziella, Romantic Perugia

Villa Graziella, Romantic Perugia
La Valle
9.6 out of 10, Exceptional, (9 reviews)
"Great place. Would stay here again."
United States
Rob B.
The price is AED 493
AED 801 total
includes taxes & fees
22 Jun - 23 Jun
Villa Graziella, Romantic Perugia
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 AED 448
AED 501 total
includes taxes & fees
22 Jun - 23 Jun
La Piccola Locanda
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 AED 761
AED 850 total
includes taxes & fees
22 Jun - 23 Jun
Abbadia Sicille Relais
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (68 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 AED 606
AED 700 total
includes taxes & fees
24 Jun - 25 Jun
Villa Curina Resort
Spa

2 Cuori e 1 Yurta Glamping in Toscana

2 Cuori e 1 Yurta Glamping in Toscana
Asciano
The price is AED 1,076
AED 1,208 total
includes taxes & fees
23 Jun - 24 Jun
2 Cuori e 1 Yurta Glamping in Toscana
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
"This was my favorite place we stayed in Italy. The property is immaculate and convenient to the city square. The staff were all so kind, professional, and personable. We loved the spa, the beautiful pool, the views, the cocktail bar on site. We will be back."
Erin 2-night trip
Posted 13 hours ago
Monastero di Cortona Hotel & 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 73 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.