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Top Holiday Rentals in Castiglion Fiorentino

Farmhouse in the hills with panoramic view and swimming pool

9.6 out of 10, Exceptional, (71)
"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

Secluded position,villa with private pool,ideal for families, close to Cortona.

9.8 out of 10, Exceptional, (57)
"Giovanna was an amazing host. She provided many recommendations and support throughout the stay. We loved staying here!"
Secluded position,villa with private pool,ideal for families, close to Cortona.

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (62)
"My fiancée and I enjoyed ourselves! It’s a beautiful place and I adored walking around in the nearby town. "
The price is £153
includes taxes & fees
26 Aug - 27 Aug
Casanova - Panoramic Rooms and Suites

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (159)
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "
The price is £120
includes taxes & fees
31 Jul - 1 Aug
Abbadia Sicille Relais

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

9.6 out of 10, Exceptional, (69)
"Samantha’s apartment was wonderful! The terrace was dreamy, with views and sunsets that I will remember for a long time! Apertivos and evenings sitting outside were lovely! The location is quiet and convenient. Lacking only a few refinements, the apartment is very desirable. "
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (121)
"Fabulous location just outside the entrance to the main part of town. Property is stylish in an olde worlde way, perfect for relaxation."
The price is £199
includes taxes & fees
8 Aug - 9 Aug
Hotel San Gregorio

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

10.0 out of 10, Exceptional, (82)
"Luigi was very helpful. We had a chef 3 nights that he helped facilitate. Beautiful location. "
Villa in Montalcino, exclusive for you, stunning view!!!

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

9.4 out of 10, Exceptional, (36)
"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 Tosco

10.0 out of 10, Exceptional, (111)
"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 £218
includes taxes & fees
8 Aug - 9 Aug
Il Tosco

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

10.0 out of 10, Exceptional, (53)
"Exvellent Location close to all towns in Tuscany Good communication w Manager"
Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

Residenza Fabroni

8.8 out of 10, Excellent, (88)
"We had a wonderful stay, the staff was extremely friendly and helpful. Restaurants and shops were right at our doorstep."
The price is £74
includes taxes & fees
4 Aug - 5 Aug
Residenza Fabroni

Osteria del Borgo

9.2 out of 10, Wonderful, (146)
"Jacopo and his family were super friendly, the restaurant is the best in Montepulciano and the views are breathtaking. If we come back we will stay at Osteria del Borgo again without a doubt. "
Osteria del Borgo

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (52)
"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 £135
includes taxes & fees
6 Aug - 7 Aug
Il Poggio dell'Eremita

Luxury Cortona view hilltop Villa

10.0 out of 10, Exceptional, (47)
"The location and accommodations are perfect for a family. Nestled in the Italian countryside providing easy access to the nearby renaissance villages, art and landscapes and the people of Italy. The accommodations that Mieke has provided will only put a smile on your face."
Luxury Cortona view hilltop Villa

Villa Graziella, Romantic Perugia

9.6 out of 10, Exceptional, (5)
"Great place. Would stay here again."
The price is £161
includes taxes & fees
21 Aug - 22 Aug
Villa Graziella, Romantic Perugia

Borgo Dolciano

9.0 out of 10, Wonderful, (24)
"We had five wonderful days in beautiful Toscana! Great atmosphere, wonderful location of the hotel and very reasonably priced. Eating at their restaurant was quite pricy however. Breakfast ok but excellent croissants and coffee! One of the reasons we picked this hotel was the laundry service which was advertised on hotels.com. No laundry service was available. "
The price is £73
includes taxes & fees
31 Jul - 1 Aug
Borgo Dolciano

Castello di Modanella

7.6 out of 10, Good, (14)
"Property is closing and looks like it. Very unfortunate, I was there 30 years ago with fond memories! Obviously I should have done more homework!! Very sad."
Castello di Modanella

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

9.8 out of 10, Exceptional, (30)
"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

Casina in authentic Tuscany

9.8 out of 10, Exceptional, (64)
"This is a charming house in a small town outside Cortona. Easily located near all the things you would want to see in the area. The host treated us like family and had homemade treats and wine waiting for our arrival. The house is perfectly suited for 4 people to stay and had a lot of charm. If you are looking to escape the hustle of daily life and relax this is the perfect location. "
Casina in authentic Tuscany

Agriturismo Borgo Spagnoli

8.6 out of 10, Excellent, (10)
"Hostess very kind and engaging. Had nice map of the area with suggested places to visit."
Agriturismo Borgo Spagnoli
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

Frequently asked questions

Are there holiday rentals in Castiglion Fiorentino?

Yes, there are holiday rentals close to the most popular sights in Castiglion Fiorentino, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Castiglion Fiorentino has to offer?

Agriturismo Borgo Spagnoli: This holiday home rental outside of Castiglion Fiorentino is located in a regional park, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a coffee maker. Kick off your shoes and enjoy yourself with a rooftop terrace and a private garden. Our travellers also rate Farmhouse in the hills with panoramic view and swimming pool as a favourite home for rent in Castiglion Fiorentino.

How many holiday rentals are there in Castiglion Fiorentino?

With 98 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Castiglion Fiorentino?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Castiglion Fiorentino. Holiday rentals provide amenities such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family trip.