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Castiglion Fiorentino Vacation Rentals

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Vacation Rentals in Castiglion Fiorentino

Farmhouse in the hills with panoramic view and swimming pool
Pool

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
Front of property - evening/night

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (70)
"My fiancée and I enjoyed ourselves! It’s a beautiful place and I adored walking around in the nearby town. "
Casanova - Panoramic Rooms and Suites
Hotel San Gregorio
Breakfast, lunch, dinner served; local cuisine

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! "
The price is ￥22,418
￥25,701 total
includes taxes & fees
Oct 29 - Oct 30
Hotel San Gregorio
Abbadia Sicille Relais
View from room

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (159)
"Great Historical location."
The price is ￥15,272
￥17,322 total
includes taxes & fees
Oct 22 - Oct 23
Abbadia Sicille Relais
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

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.
Outdoor dining

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
Outdoor dining

Hilltop house in the heart of Tuscany with private pool

9.8 out of 10, Exceptional, (92)
"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
Lobby

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."
The price is ￥12,168
￥14,079 total
includes taxes & fees
Oct 9 - Oct 10
Residenza Fabroni
17th century farmhouse with private pool and Wi-Fi and air conditioning
Outdoor pool

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
Exterior

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (55)
"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."
The price is ￥20,546
￥24,032 total
includes taxes & fees
Oct 11 - Oct 12
Il Poggio dell'Eremita
Il Tosco
Property entrance

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 "
The price is ￥46,890
￥52,273 total
includes taxes & fees
Oct 24 - Oct 25
Il Tosco
Delcorto Suites
Interior

Delcorto Suites

10.0 out of 10, Exceptional, (28)
"Exceptional service great building felt like a Medici!"
The price is ￥27,927
￥31,414 total
includes taxes & fees
Oct 2 - Oct 3
Delcorto Suites
Villa Graziella, Romantic Perugia
Outdoor pool

Villa Graziella, Romantic Perugia

9.6 out of 10, Exceptional, (7)
"Great place. Would stay here again."
The price is ￥16,871
￥29,195 total
includes taxes & fees
Oct 15 - Oct 16
Villa Graziella, Romantic Perugia
Luxury Cortona view hilltop Villa
Outdoor dining

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
Property grounds

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!
Outdoor pool

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
Exterior

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
Pool

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
Outdoor spa tub

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
Exterior

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.
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Top Castiglion Fiorentino Hotel Reviews

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

10/10 Excellent
"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."
Charles 2-night trip
Posted 11 hours ago
Casanova - Panoramic Rooms and Suites

Find out more about Castiglion Fiorentino

Find out more about Castiglion Fiorentino

Search for holiday rentals in Castiglion Fiorentino on Expedia! You can easily find your home rentals, villas, holiday apartments in Castiglion Fiorentino using one of the methods below:

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Look no further and take a look at our great range of rental properties in Castiglion Fiorentino!

Explore a world of travel with Expedia

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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?

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.