Castiglion Fiorentino Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Castiglion Fiorentino vacation rentals

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 CA $186
CA $212 total
includes taxes & fees
May 23 - May 24
San Michele al Borgo

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 CA $160
CA $224 total
includes taxes & fees
May 18 - May 19
The window on the tower apartment new castiglion fiorentino

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 CA $167
CA $202 total
includes taxes & fees
May 19 - May 20
Casa Lèon, Relax Nature and Comfort in the Heart of Valdichiana.

Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is CA $115
CA $150 total
includes taxes & fees
Jun 1 - Jun 2
Happy Nest Tuscany Between Florence and Rome

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 CA $762
CA $765 total
includes taxes & fees
May 18 - May 19
Apartment 'Granaio - Borgo Dolci Colline' with Private Pool, Wi-Fi, and Air Conditioning

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 CA $192
CA $211 total
includes taxes & fees
May 19 - May 20
Villa Cassia di Baccano

Villa La Ginestra

Villa La Ginestra
Subbiano
9.6 out of 10, Exceptional, (5 reviews)
"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."
Canada
Philippe
The price is CA $145
CA $160 total
includes taxes & fees
Jun 14 - Jun 15
Villa La Ginestra

Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (5 reviews)
"Amazing stay at this hotel I would recommend it. Great hospitality, clean and picture postcard views. "
United Kingdom
Liam
The price is CA $438
CA $485 total
includes taxes & fees
May 18 - May 19
Fontelunga Hotel & Villas

Villa Graziella, Romantic Perugia

Villa Graziella, Romantic Perugia
La Valle
9.6 out of 10, Exceptional, (8 reviews)
"excellent stay. Beautiful pool, well equipped kitchen, very friendly host.Perfect for the visit of the surrondigns: Perugia, the lake, Montepulciano."
United States
cinzia c.
The price is CA $160
CA $272 total
includes taxes & fees
May 18 - May 19
Villa Graziella, Romantic Perugia

Eagle House

Eagle House
CHIANCIANO
10.0 out of 10, Exceptional, (3 reviews)
"Paolo and Monica were such gracious and enthusiastic hosts. The property is beautiful, and the hospitality was great. Paolo and Monica helped plan our itinerary each day which made for a stress-free week. The highlight was the interaction with owls, eagles, and other animals, as well as the wine cave and the history behind it. Thanks again, Paolo and Monica! "
United States
Rob C.
The price is CA $288
CA $420 total
includes taxes & fees
May 18 - May 19
Eagle House

TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (2 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is CA $142
CA $163 total
includes taxes & fees
Jun 2 - Jun 3
TuscanyLettings Studio&Room

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 CA $161
CA $181 total
includes taxes & fees
May 23 - May 24
La Piccola Locanda

L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (24 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is CA $1,007
CA $1,114 total
includes taxes & fees
Jun 9 - Jun 10
L'Olmo

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (174 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is CA $242
CA $271 total
includes taxes & fees
May 19 - May 20
Abbadia Sicille Relais

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (84 reviews)
"We loved our stay and wish we could have stayed longer. Our room was clean & comfortable. The view was AMAZING. We had breakfast included daily which was very good and had a bunch of gluten free options. Our bodies were tired after the hustle & bustle of Florence & Rome so we booked into the “light spa” and had the hot pools to ourselves. It was a short walk to town. We wish we could have stayed longer and plan to be back. "
Canada
Ron
The price is CA $259
CA $291 total
includes taxes & fees
May 26 - May 27
Casanova - Panoramic Rooms and Suites

Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
The price is CA $309
CA $348 total
includes taxes & fees
May 25 - May 26
Albergo Diffuso Borgo Santo

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (142 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is CA $269
CA $306 total
includes taxes & fees
Jun 7 - Jun 8
Hotel San Gregorio

Dolce Casa 2 Summary:

Dolce Casa 2 Summary:
Arezzo
The price is CA $123
CA $171 total
includes taxes & fees
May 18 - May 19
Dolce Casa 2 Summary:

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (138 reviews)
"Beautiful quaint place to stay in Montepulciano. Stairs are doable to carry up luggage and the views of the valley are spectacular. Great location, can’t wait to stay again!"
Canada
Melissa
The price is CA $249
CA $280 total
includes taxes & fees
Jun 11 - Jun 12
La Locanda di San Francesco

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 CA $224
CA $262 total
includes taxes & fees
May 27 - May 28
Apartment 'La Dimora Di Pienza in Val D'Orcia' with Wi-Fi
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Castiglion Fiorentino Hotel Reviews

Find out more about Castiglion Fiorentino

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Castiglion Fiorentino. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Farmhouse in the hills with panoramic view and swimming pool: This highly rated vacation home rental in Castiglion Fiorentino is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 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. Our travelers also rate Farmhouse in Tuscany with Private Pool as a favorite home for rent in Castiglion Fiorentino.

How many vacation rentals are there in Castiglion Fiorentino?

With 68 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.