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

Castiglion Fiorentino Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Castiglion Fiorentino vacation rentals

A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

1. 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
$131 nightly
The price is $149
Oct 30 - Oct 31
Total with taxes and fees
San Michele al Borgo
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

2. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (166 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
$145 nightly
The price is $166
Nov 9 - Nov 10
Total with taxes and fees
Hotel San Gregorio
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

3. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.4 out of 10, Exceptional, (48 reviews)
"Roberto, his wife and his staff were all round great. Very friendly helpful and great service. We were very happy to find this authentic castle/village to stay in Tuscany."
Canada
Iain
$242 nightly
The price is $271
Oct 24 - Oct 25
Total with taxes and fees
Castello di Gargonza
A historic building with a tower, a courtyard, and a well-lit entrance.

4. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
$71 nightly
The price is $81
Nov 23 - Nov 24
Total with taxes and fees
Abbadia Sicille Relais
A poolside area with two glasses of water, candles, and a stone pathway.

5. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (102 reviews)
"The variety at the buffet was really good and the coffee machines made really good coffee. The site itself was very nice and well maintained. The problem with this place is the reception for arrival and departure, no service and fast to dismiss you."
Canada
DANIELA
$166 nightly
The price is $187
Oct 27 - Oct 28
Total with taxes and fees
Casanova - Panoramic Rooms and Suites
A hot tub with two people, surrounded by trees and a wooden deck.

6. 2 Cuori e 1 Yurta Glamping in Toscana

2 Cuori e 1 Yurta Glamping in Toscana
Asciano
$238 nightly
The price is $268
Nov 2 - Nov 3
Total with taxes and fees
2 Cuori e 1 Yurta Glamping in Toscana
A villa with a swimming pool, outdoor seating, and a tennis court.

7. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (81 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
$135 nightly
The price is $153
Oct 24 - Oct 25
Total with taxes and fees
Villa Curina Resort
An interior courtyard with stone columns, arches, and a mosaic.

8. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (119 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
$149 nightly
The price is $168
Oct 31 - Nov 1
Total with taxes and fees
Meublé Il Riccio
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

9. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (28 reviews)
"We were so comfortable and impressed with L'Olmo. Communication prior to our trip was perfect. We got there and the grounds were immaculate, the room was stunning, and the location was extremely convenient. The staff was very helpful. We loved staying here and can recommend it whole heartedly."
United States
Michelle
$449 nightly
The price is $498
Nov 4 - Nov 5
Total with taxes and fees
L'Olmo
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

10. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (143 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
$106 nightly
The price is $121
Nov 1 - Nov 2
Total with taxes and fees
Bed & Breakfast Vicolo dell'Oste
A crowded restaurant with brick walls and multiple tables and chairs.

11. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (151 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
$160 nightly
The price is $180
Nov 7 - Nov 8
Total with taxes and fees
La Locanda di San Francesco
A spa area with a stone-walled arch, a hot tub, and a small window.

12. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (30 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
$103 nightly
The price is $118
Nov 8 - Nov 9
Total with taxes and fees
DormiVeglia B&B
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

13. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
$170 nightly
The price is $187
Oct 31 - Nov 1
Total with taxes and fees
Villa di Sotto
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

14. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (138 reviews)
"Excellent room, service and food. The best."
United States
Valerie
$231 nightly
The price is $259
Nov 3 - Nov 4
Total with taxes and fees
Il Tosco
Pool

15. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (41 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
$74 nightly
The price is $89
Nov 16 - Nov 17
Total with taxes and fees
iConic Wellness Resort
A cozy living room with a stone wall, a wine rack, and two sofas.

16. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (27 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
$107 nightly
The price is $118
Nov 22 - Nov 23
Total with taxes and fees
Villa Cassia di Baccano
A hotel room with a bed, a bedside table, a mirror, and a ceiling with wooden beams.

17. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
9.0 out of 10, Wonderful, (4 reviews)
"I really liked the brand new room. Nice design and super comfy bed. Plus free coffee is a nice addition to the experience there. Loved it. Plus my personal highlight were the nice views into the historical center of Arezzo."
Germany
Florian
$85 nightly
The price is $99
Oct 25 - Oct 26
Total with taxes and fees
Limehome Arezzo Duomo
An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

18. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.4 out of 10, Exceptional, (26 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
$142 nightly
The price is $159
Nov 7 - Nov 8
Total with taxes and fees
B&B Piccolo Hotel
An arched doorway leading to a building with a wooden door and a staircase.

19. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (115 reviews)
"Very charming property in a fantastic location. The host was very responsive and we had a marvelous stay. Bear in mind this is a historic property and accordingly has some quirks. Those looking for modernity and perfect fixtures may not appreciate those quirks."
United States
Marc
$90 nightly
The price is $103
Oct 29 - Oct 30
Total with taxes and fees
Residenza Fabroni
A modern hotel room with large windows, a bed, a desk, and a chair.

20. B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.2 out of 10, Very good, (84 reviews)
"Very accessible and easy accommodation. Very pleasant room and reasonable breakfast. Within walking distance of train station and city centre."
Australia
Tina
$71 nightly
The price is $85
Nov 3 - Nov 4
Total with taxes and fees
B&B 52cento
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

Nuovo Etruria Resort

Nuovo Etruria Resort

8/10 Good
"When we arrived the gate to the hotel was locked. Called the hotel and then a person drove up and helped us to check in. He was very nice. The hotel is very old, but a decent place to stay for a night."
John 1-night trip
Posted 22 hours ago
Nuovo Etruria Resort

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 $62 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.

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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?

Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!: This vacation home rental near Castiglion Fiorentino is located in a rural location and has an outdoor pool, a patio, and air-conditioning to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Castiglion Fiorentino?

With 85 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?

Enjoy the area's cultural attractions such as Museo Diocesano, or get outdoors into nature at a spot like Val di Chiana. Tennis Club Castiglionese and Vasari Loggia 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.