A historic town with a prominent church tower, surrounded by rolling hills and vineyards.

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Castiglion Fiorentino holiday rentals

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
The price is 3.769.224 ₫
4.266.324 ₫ total
includes taxes & fees
5 Jul - 6 Jul
San Michele al Borgo
Lobby

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 3.905.574 ₫
4.296.131 ₫ total
includes taxes & fees
2 Jul - 3 Jul
Villa Cassia di Baccano
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, (91 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is 4.967.864 ₫
5.584.979 ₫ total
includes taxes & fees
5 Jul - 6 Jul
Casanova - Panoramic Rooms and Suites
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
The price is 1.888.460 ₫
2.197.484 ₫ total
includes taxes & fees
2 Jul - 3 Jul
Residenza Fabroni
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
The price is 4.154.340 ₫
4.659.908 ₫ total
includes taxes & fees
2 Jul - 3 Jul
Abbadia Sicille Relais
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (69 reviews)
"This was our second stay. The property is beautiful and our room was lovely. The breakfast was one of the best on our trip in Italy."
Canada
Dr Anne
The price is 4.798.385 ₫
5.518.580 ₫ total
includes taxes & fees
2 Jul - 3 Jul
Villa Curina Resort
Classic Apartment, Vineyard View | Interior

Podere Tre Berte - The Sleeping Beauty

Podere Tre Berte - The Sleeping Beauty
Toscana
Podere Tre Berte - The Sleeping Beauty
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
The price is 2.101.752 ₫
2.462.150 ₫ total
includes taxes & fees
20 Jul - 21 Jul
RESIDENCE LECCIO
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (148 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is 5.682.161 ₫
6.430.644 ₫ total
includes taxes & fees
22 Jul - 23 Jul
Hotel San Gregorio
Suite, 2 Bedrooms | Courtyard view

L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (25 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is 12.017.814 ₫
13.339.773 ₫ total
includes taxes & fees
27 Jul - 28 Jul
L'Olmo
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (111 reviews)
"It was very well located ."
Canada
Marlenne
The price is 4.281.346 ₫
4.829.658 ₫ total
includes taxes & fees
2 Jul - 3 Jul
Meublé Il Riccio
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
The price is 3.191.549 ₫
3.570.793 ₫ total
includes taxes & fees
2 Jul - 3 Jul
La Piccola Locanda
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (145 reviews)
"Great location."
United States
James
The price is 3.823.768 ₫
4.326.323 ₫ total
includes taxes & fees
16 Jul - 17 Jul
La Locanda di San Francesco
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (34 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
The price is 4.493.078 ₫
4.942.386 ₫ total
includes taxes & fees
5 Jul - 6 Jul
Villa di Sotto
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, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is 2.462.599 ₫
2.829.037 ₫ total
includes taxes & fees
14 Jul - 15 Jul
DormiVeglia B&B
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

Il Borro - Relais & Châteaux

Il Borro - Relais & Châteaux

10/10 Excellent
"Wonderful place to stay for part of our honeymoon! The staff were wonderful and so helpful. There is so much to do within the village and the food was amazing. We will be back!"
Nichole 3-night trip
Posted 12 hours ago
Il Borro - Relais & Châteaux

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.

How many holiday rentals are there in Castiglion Fiorentino?

With 74 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. Cassero Tower and Tennis Club Castiglionese 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.