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
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

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
$113 nightly
The price is $118
Jul 9 - Jul 10
Total with taxes and fees
Happy Nest Tuscany Between Florence and Rome
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
$127 nightly
The price is $145
Jul 20 - Jul 21
Total with taxes and fees
San Michele al Borgo
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.
$158 nightly
The price is $160
Jul 9 - Jul 10
Total with taxes and fees
The window on the tower apartment new castiglion fiorentino
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
$828 nightly
The price is $830
Jul 9 - Jul 10
Total with taxes and fees
Apartment 'Granaio - Borgo Dolci Colline' with Private Pool, Wi-Fi, and Air Conditioning
Lobby

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (24 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
$132 nightly
The price is $146
Jul 8 - Jul 9
Total with taxes and fees
Villa Cassia di Baccano
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
$126 nightly
The price is $146
Jul 8 - Jul 9
Total with taxes and fees
iConic Wellness Resort
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
$121 nightly
The price is $136
Jul 9 - Jul 10
Total with taxes and fees
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
$88 nightly
The price is $100
Jul 13 - Jul 14
Total with taxes and fees
Abbadia Sicille Relais
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
$80 nightly
The price is $94
Jul 12 - Jul 13
Total with taxes and fees
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, (92 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
$174 nightly
The price is $196
Jul 15 - Jul 16
Total with taxes and fees
Casanova - Panoramic Rooms and Suites
Outdoor dining

Holiday home with panoramic terrace ideal for families and couples

Holiday home with panoramic terrace ideal for families and couples
Cortona
$93 nightly
The price is $93
Jul 9 - Jul 10
Total with taxes and fees
Holiday home with panoramic terrace ideal for families and couples
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
$75 nightly
The price is $87
Jul 13 - Jul 14
Total with taxes and fees
Residenza Fabroni
Outdoor dining

Deluxe room Cartazucchero in the heart of Arezzo

Deluxe room Cartazucchero in the heart of Arezzo
Arezzo Centro Storico
10.0 out of 10, Exceptional, (3 reviews)
"From all the places we stayed during our 13-day trip to Italy, this was by far our favorite. Fabio was incredibly communicative and friendly right from the start, sending us clear instructions on how to get there. He greeted us at the door with such warmth that it truly felt like we were staying with family. The room was spotless, beautifully decorated, and generously stocked with water, cookies, pastries, and other treats. It had the comfort and attention to detail of a hotel, yet the warmth of...
United States
Hector
$84 nightly
The price is $92
Jul 8 - Jul 9
Total with taxes and fees
Deluxe room Cartazucchero in the heart of Arezzo
Outdoor dining

Dolce Casa 2 by Tiny Away

Dolce Casa 2 by Tiny Away
Arezzo
$122 nightly
The price is $122
Jul 8 - Jul 9
Total with taxes and fees
Dolce Casa 2 by Tiny Away
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (35 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
$156 nightly
The price is $171
Jul 20 - Jul 21
Total with taxes and fees
Villa di Sotto
1 bedroom, WiFi, bed sheets

Dolce Casa 1 by Tiny Away

Dolce Casa 1 by Tiny Away
Arrezo
$129 nightly
The price is $129
Jul 12 - Jul 13
Total with taxes and fees
Dolce Casa 1 by Tiny Away
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (29 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
$93 nightly
The price is $107
Jul 8 - Jul 9
Total with taxes and fees
DormiVeglia B&B
Apartment (1 Bedroom) | Front of property

Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
$93 nightly
The price is $107
Jul 8 - Jul 9
Total with taxes and fees
Vicolo Della Scala Rooms - La Luna
Junior Suite | Terrace/patio

Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
$131 nightly
The price is $148
Jul 25 - Jul 26
Total with taxes and fees
Casale dell'Assiolo
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
$182 nightly
The price is $182
Jul 8 - Jul 9
Total with taxes and fees
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
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

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

10/10 Excellent
"Our stay at Casanova Panoramic Rooms was absolutely wonderful. The room was beautiful, spotless, and the view was simply breathtaking. The entire check-in process was smooth and welcoming, and having convenient parking made everything even easier. We also loved the restaurant—the food was delicious, and breakfast was excellent. Every part of our stay exceeded our expectations. We would definitely stay here again and highly recommend it to anyone visiting the area."
Anonymous traveler 2-night trip
Posted 12 hours ago
Casanova - Panoramic Rooms and Suites

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 $87 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?

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 75 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. Archaeological Museum 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.