Photo by Sophia Field

Search Holiday Rentals in Castiglion Fiorentino

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
15 Nov - 16 Nov
Tomorrow
16 Nov - 17 Nov
Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov

Top Holiday Rentals in Castiglion Fiorentino

Free daily cooked-to-order breakfast
San Michele al Borgo

San Michele al Borgo

Castiglion Fiorentino
9.8 out of 10, Exceptional, (9)
"Very caring and friendly staff!"
United States
Andrea
The price is 3.426.854 ₫
3.830.833 ₫ total
includes taxes & fees
23 Nov - 24 Nov
San Michele al Borgo
Lunch, dinner served; Italian cuisine, garden views
Locanda del Viandante

Locanda del Viandante

Anghiari
9.0 out of 10, Wonderful, (6)
"Smuk beliggenhed - meget autentisk på den gode måde"
Denmark
tina
The price is 3.758.205 ₫
4.133.934 ₫ total
includes taxes & fees
16 Nov - 17 Nov
Locanda del Viandante
Lobby lounge
Villa Cassia di Baccano

Villa Cassia di Baccano

Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is 3.771.206 ₫
4.148.327 ₫ total
includes taxes & fees
27 Nov - 28 Nov
Villa Cassia di Baccano
Deluxe Double Room | View from room
Affitacamere Maria Gabriella

Affitacamere Maria Gabriella

Pienza
9.8 out of 10, Exceptional, (51)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella
Property entrance
Il Tosco

Il Tosco

Montepulciano
10.0 out of 10, Exceptional, (112)
"Stunning views. Excellent hostess! Fabulous breakfast!! Would definitely stay again if ever back"
Canada
stephen
The price is 6.914.944 ₫
7.728.925 ₫ total
includes taxes & fees
16 Nov - 17 Nov
Il Tosco
Front of property – evening/night
Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (78)
"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."
United States
Charles
The price is 4.955.153 ₫
5.573.156 ₫ total
includes taxes & fees
16 Nov - 17 Nov
Casanova - Panoramic Rooms and Suites
Interior
Delcorto Suites

Delcorto Suites

Montepulciano
10.0 out of 10, Exceptional, (32)
"Everything is great. The family owns the property over 600 years. Great breakfast, fabulous suite. "
United States
Liping
The price is 4.693.643 ₫
5.285.495 ₫ total
includes taxes & fees
16 Nov - 17 Nov
Delcorto Suites
Terrace/patio
Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci

Pergine Valdarno
9.4 out of 10, Exceptional, (3)
"We absolutely loved our stay at this hotel. The suite was perfect and the restaurant had probably the best food I have had in Tuscany. We definitely plan to stay there again."
United States
Gregory
The price is 3.287.467 ₫
3.708.153 ₫ total
includes taxes & fees
16 Nov - 17 Nov
Casa Vacanze Le Fornaci
Garden
La Murata

La Murata

Rapolano Terme
9.0 out of 10, Wonderful, (11)
"Lovely property in a great location. Lots of space. They have a Nespresso machine (perhaps they could have provided a couple of capsules too). The pool was excellent. "
United States
Ron
The price is 3.908.446 ₫
4.421.778 ₫ total
includes taxes & fees
22 Nov - 23 Nov
La Murata
Exterior
Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste

Montepulciano
9.6 out of 10, Exceptional, (127)
"Great hosts, central location "
United States
Alexander
The price is 3.156.794 ₫
3.594.991 ₫ total
includes taxes & fees
25 Nov - 26 Nov
Bed & Breakfast Vicolo dell'Oste
Exterior
Meublé Il Riccio

Meublé Il Riccio

Montepulciano
9.6 out of 10, Exceptional, (85)
"This was a great location, great hotel, and our room had a wonderful view!!! Would highly recommend for a small boutique hotel in town!"
United States
Melissa
Meublé Il Riccio
Front of property
Locanda Antico Borgo

Locanda Antico Borgo

Civitella in Val di Chiana
9.2 out of 10, Wonderful, (20)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
The price is 3.062.173 ₫
3.368.390 ₫ total
includes taxes & fees
27 Nov - 28 Nov
Locanda Antico Borgo
Exterior
Podere La Chiusella

Podere La Chiusella

Rapolano Terme
9.4 out of 10, Exceptional, (30)
"Et sjarmerende lite B&B. Har nok vært utrolig vakkert i sine glansdager, men områdene rundt bærer preg av lite vedlikehold. Leiligheten var helt grei for en overnatting. Gulvet på badet var ikke rent. Når vi tørket opp etter oss ble håndkleet møkkete. Men overnattingen var helt grei alt i alt. Når vi skulle sjekke ut var det ikke et menneske å se, resepsjonen var stengt. Endte med å sette nøklene i døra og dra da alt var betalt ved bestilling."
Norway
Elisabeth
Podere La Chiusella
Classic Double or Twin Room, 1 Double Bed | Premium bedding, down duvets, pillow-top beds, minibar
THE MONNA LISA RESORT

THE MONNA LISA RESORT

Arezzo
9.6 out of 10, Exceptional, (8)
"El personal fue de lo más atento y amigable."
Mexico
Gretta
The price is 4.325.359 ₫
4.941.774 ₫ total
includes taxes & fees
19 Nov - 20 Nov
THE MONNA LISA RESORT
Property grounds
Artisti del Cavallo Tourism

Artisti del Cavallo Tourism

Foiano della Chiana
8.4 out of 10, Very good, (24)
"Ottimo agriturismo silenzioso con persone molto gentilissime "
Italy
GIANCARLO
The price is 2.142.129 ₫
2.417.585 ₫ total
includes taxes & fees
17 Nov - 18 Nov
Artisti del Cavallo Tourism
Bar (on property)
La Piccola Locanda

La Piccola Locanda

Chiusi
8.8 out of 10, Excellent, (8)
"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
La Piccola Locanda
Seasonal outdoor pool
Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo

Asciano
The price is 6.736.781 ₫
7.563.568 ₫ total
includes taxes & fees
21 Nov - 22 Nov
Albergo Diffuso Borgo Santo
Breakfast, lunch, dinner served; local cuisine
Hotel San Gregorio

Hotel San Gregorio

3.0 star property
Pienza
9.4 out of 10, Exceptional, (133)
"Excellent property! Very elegant and the service was wonderful. The breakfast was also excellent. The location could not be any better - the entry to the old town is just across from the hotel. Wish we could have stayed longer."
United States
DEBORAH
The price is 4.584.908 ₫
5.227.129 ₫ total
includes taxes & fees
5 Dec - 6 Dec
Hotel San Gregorio
Room, 1 Bedroom, Accessible, Smoking | Interior
Room in Apartment - Two-room Apartment

Room in Apartment - Two-room Apartment

Arezzo
10.0 out of 10, Exceptional, (1)
"A little tricky to locate but friendly staff and very walkable to see the sites."
Canada
Thelma
The price is 3.215.282 ₫
3.720.540 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Room in Apartment - Two-room Apartment
Exterior
Castello di Gargonza

Castello di Gargonza

3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (39)
"All of the hotel staff did an outstanding job. Our room had everything we needed and the restaurant was great. Breakfast was exceptional. Special shoutout to Neri, the owner, for taking such good care of us. "
United States
Diane
Castello di Gargonza
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castiglion Fiorentino Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"What a unique place. Near the top of the hill. Staff service and amenities were all great. Not an easy place to drive to. The taxis drive-in backwards the last eighth of a mile."
john 2-night trip
Posted 11 days ago
Monastero di Cortona Hotel & Spa

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 97 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.