Photo by Sophia Field

Castiglion Fiorentino Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    bundle and save illustration

    Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
    one key illustration

    OneKeyCash

    Earn OneKeyCash on all your eligible bookings
    ftc illustration

    Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

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

Vacation Rentals in Castiglion Fiorentino

Farmhouse in the hills with panoramic view and swimming pool

9.6 out of 10, Exceptional, (74)
"We‘ve spent two wonderful weeks with our two year old daughter and our dog. The house is beautifully located in the hills with no direct neighbours. The view is fantastic and we felt immediately at home in this beautiful house. We had a wonderful time and our hosts were just lovely. (We cannot say anything about the pool - except that it is huge - because we were there out of season in March when the pool was closed.)"
Farmhouse in the hills with panoramic view and swimming pool

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (70)
"Delightful stay. The room was lovely, and the view from our private terrace was wonderful. Dinner was first rate. Easily walkable into San Quirico, short drive to Montalcino, Pienza, and Montalcino. Nice massage and spa. A very good value."
$175 nightly
The price is $198
Oct 9 - Oct 10
Total with taxes and fees
Casanova - Panoramic Rooms and Suites

Hotel San Gregorio

3.0 star property
9.4 out of 10, Exceptional, (129)
"Such friendly staff, loved Pienza and the property was such a good location! "
$121 nightly
The price is $140
Nov 4 - Nov 5
Total with taxes and fees
Hotel San Gregorio

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (159)
"Great Historical location."
$76 nightly
The price is $88
Nov 4 - Nov 5
Total with taxes and fees
Abbadia Sicille Relais

Villa in Montalcino, exclusive for you, stunning view!!!

10.0 out of 10, Exceptional, (84)
"Lovely villa in a beautiful location. "
Villa in Montalcino, exclusive for you, stunning view!!!

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

9.6 out of 10, Exceptional, (71)
"My husband and I loved our stay here! It was so close to town and the terrace was absolutely stunning. Would definitely stay here again! "
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

Hilltop house in the heart of Tuscany with private pool

9.8 out of 10, Exceptional, (93)
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."
Hilltop house in the heart of Tuscany with private pool

Residenza Fabroni

8.8 out of 10, Excellent, (90)
"We had a wonderful stay, the staff was extremely friendly and helpful. Restaurants and shops were right at our doorstep."
$88 nightly
The price is $102
Oct 24 - Oct 25
Total with taxes and fees
Residenza Fabroni

17th century farmhouse with private pool and Wi-Fi and air conditioning

9.2 out of 10, Wonderful, (39)
"Our host Maurizio, added quite a few extra layers of enjoyment to our stay. A brilliant host who went above and beyond to make our holiday truely memorable! We have invited him to come stay with us when he visits Australia. As for the farm house it’s self, an amazing experience to live like a true Italian. If you want to experience country life, I recommend La Rustica! Thank you Maurizio and Simonetta. ❤️"
17th century farmhouse with private pool and Wi-Fi and air conditioning

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (56)
"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."
$160 nightly
The price is $162
Oct 11 - Oct 12
Total with taxes and fees
Il Poggio dell'Eremita

Il Tosco

10.0 out of 10, Exceptional, (112)
"The people here are authentic and welcoming! The building, rooms and facilities are gorgeous! One of our most beautiful stays in our many trips to Italy "
$277 nightly
The price is $310
Nov 4 - Nov 5
Total with taxes and fees
Il Tosco

Delcorto Suites

10.0 out of 10, Exceptional, (28)
"Exceptional service great building felt like a Medici!"
$210 nightly
The price is $236
Oct 8 - Oct 9
Total with taxes and fees
Delcorto Suites

Villa Graziella, Romantic Perugia

9.6 out of 10, Exceptional, (7)
"Great place. Would stay here again."
$198 nightly
The price is $198
Oct 8 - Oct 9
Total with taxes and fees
Villa Graziella, Romantic Perugia

Luxury Cortona view hilltop Villa

10.0 out of 10, Exceptional, (48)
"Perfect location for day trips covering so many of the hilltop towns. Perfect accommodation for a group of 12 friends as each bedroom has it’s own bathroom.Perfect Villa for relaxing at home coffee every morning, lying by the pool and dinner watching the incredible sunsets.Perfect hosts. Denise takes care of everything while you are at the villa including cooking us a wonderful dinner. Mieke answered all our questions prior to our arrival very promptly. She has set the villa up perfectly and...
Luxury Cortona view hilltop Villa

Beautiful renovated stone villa - private pool,park,air conditioning,smart tv

9.8 out of 10, Exceptional, (35)
"We love our stay st Ca de Santi. Everything was great and the property is really amazing. You feel the Tuscany atmosphere."
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv

Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

10.0 out of 10, Exceptional, (56)
"Beautiful property comfortable beds. Amazing views room two sit outside and enjoy sunsets."
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

Casina in authentic Tuscany

9.8 out of 10, Exceptional, (68)
"My mom and I stayed at Casina del Bibo for four days. The location is perfect if you want to stay in a small village away from all of the hustle of the Tuscan hill towns. You will definitely need a car, though. We stayed in the upstairs apartment, which had two large rooms with king sized beds (and air conditioning, which was much needed!). The sitting room is cozy. There is a small kitchen that seems well equipped, although we didn't cook anything. Anna Maria and her daughter Lorella were very...
Casina in authentic Tuscany

Il Casale Di Manuele 12, Emma Villas

10.0 out of 10, Exceptional, (3)
"We loved this home - everything was perfect and it was easy to find and enjoy. I highly recommend the next time you are wanting to stay in Tuscany! "
Il Casale Di Manuele 12, Emma Villas

Typical Tuscan Residence near the farm la Vialla

9.2 out of 10, Wonderful, (13)
"Das Haus ist über 300 Jahre alt und gut restauriert. Wir haben von dort aus Sehenswürdigkeiten besucht und bewundert, wie z. B. Siena. Nach den Ausflügen konnten wir uns am Pool abkühlen.Die Gastgeber waren immer für uns ansprechbar und haben uns viele Tipps gegeben, auch zu Flussbadestellen, die wir gern besucht haben."
Typical Tuscan Residence near the farm la Vialla

Podere La Chiusella

9.4 out of 10, Exceptional, (30)
Podere La Chiusella
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

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 $88 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.

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?

Agriturismo Borgo Spagnoli: Located near Castiglion Fiorentino, this vacation home rental is located in a regional park and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. Kick off your shoes and enjoy yourself with a rooftop terrace and a private yard. Our travelers also rate Farmhouse in the hills with panoramic view and swimming pool as a favorite home for rent in Castiglion Fiorentino.

How many vacation rentals are there in Castiglion Fiorentino?

With 97 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. Tennis Club Castiglionese and Agricola Buccelletti Winery 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.