Photo by Pigellino (CC BY)

Castiglion Fiorentino vacation rentals

We found 2,357 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Castiglion Fiorentino by choosing from 98 houses, 37 apartments, and other vacation rentals. Vacation homes provide the best amenities for you and your friends, family, or even pets, such as parking and a washer and dryer. At the end of the day, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Castiglion Fiorentino

Showing deals for:Nov 14 - Nov 21

Image gallery for Beautiful Tuscan farmhouse in the countryside with swimming pool

Pool
10 out of 10 rating
Exceptional
(7 reviews)

Beautiful Tuscan farmhouse in the countryside with swimming pool

Cortona, Tuscany

5% off
Price is CA $830
CA $6,462 total
includes taxes & fees
Beautiful Tuscan farmhouse in the countryside with swimming pool

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Castiglion Fiorentino

Find out more about Castiglion Fiorentino

The historic area of Castiglion Fiorentino awaits your stay

Take a vacation to Castiglion Fiorentino and enjoy the area's history, culture and wineries. This city's horse racing, horseback riding and churches draw many visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Castiglion Fiorentino

Are you looking for things to do in the area? Venture out of your vacation home and experience everything that makes Castiglion Fiorentino a one-of-a-kind vacation spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Arezzo Equestrian Centre (7.5 mi / 12 km)
  • La Braccesca Winery (12.3 mi / 19.8 km)
  • Terme Antica Querciolaia (16.3 mi / 26.2 km)
  • San Giovanni Terme Rapolano (17.2 mi / 27.7 km)
  • Villa a Sesta Polo Club (18.3 mi / 29.5 km)
  • Cantina del Redi (18.6 mi / 29.9 km)

Exploring the natural features in Castiglion Fiorentino

Whether you're an active traveler or just want to spend some time taking in the scenery, Castiglion Fiorentino is a great place to get outside. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Piazza Guido Monaco (8.7 mi / 14 km)
  • Isola Maggiore (14.2 mi / 22.9 km)
  • Sualzo Beach (15.7 mi / 25.3 km)
  • Terme Antica Querciolaia (16.3 mi / 26.2 km)
  • Lake Trasimeno (17 mi / 27.3 km)
  • Val di Chiana (18.6 mi / 30 km)

Traveling to and around Castiglion Fiorentino

The nearest airport is in Sant Egidio Airport (PEG), located 33.7 mi (54.3 km) from the city center.

If you prefer train travel, the main station serving the city is Castiglion Fiorentino Station.

Frequently asked questions

What is the best area to stay in Castiglion Fiorentino when booking a vacation rental?
When considering a vacation rental in Castiglion Fiorentino, the historic centre is a popular area to stay. This charming neighbourhood offers a delightful blend of medieval architecture and stunning views of the surrounding Tuscan countryside. While wandering through its narrow, cobblestone streets, you can marvel at the well-preserved ancient buildings and visit the impressive Cassero, a fortress that provides panoramic vistas of the region.

Another appealing area is the outskirts of the town, where you can find properties with beautiful gardens and scenic landscapes. This area is great for those seeking a more tranquil retreat while still being within easy reach of the town's attractions. Here, you can enjoy the serenity of the countryside and explore nearby vineyards, which are a hallmark of the Tuscan experience.
How much does it cost to rent a vacation home in Castiglion Fiorentino?
Prices for vacation rentals in Castiglion Fiorentino vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Castiglion Fiorentino to more spacious homes.
Are there any discounts for Castiglion Fiorentino vacation house rentals?
You can find great discounts on house rentals in Castiglion Fiorentino on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Castiglion Fiorentino?
In Castiglion Fiorentino, villas are the most popular type of vacation rental, with around 108 available throughout the picturesque Tuscan landscape. These villas often feature traditional architecture, spacious gardens, and private pools, providing an ideal setting for relaxation while enjoying stunning views of the surrounding countryside. Additionally, there are approximately 90 vacation houses that offer a similar charm, usually equipped with fully fitted kitchens, comfortable living areas, and outdoor dining spaces for al fresco meals.
Are there any family house rentals in Castiglion Fiorentino?
In Castiglion Fiorentino, Tuscany, there are numerous family-friendly house rentals available, with around 114 options to choose from. This charming town offers a fantastic blend of history and natural beauty, making it an ideal destination for families seeking an enjoyable getaway.

Visitors can find spacious homes featuring amenities such as fully equipped kitchens, ample living spaces for relaxation, and outdoor areas where children can play safely. Many properties also provide conveniences like Wi-Fi and air conditioning, ensuring a comfortable stay for all family members.
Can I rent a vacation home with a pool or hot tub in Castiglion Fiorentino?
In Castiglion Fiorentino, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 197 options to choose from. This picturesque town in Tuscany provides a wonderful setting for travellers seeking relaxation and leisure. Many of these properties come with amenities such as private swimming pools, inviting hot tubs, and spacious outdoor terraces, ideal for enjoying the stunning views of the surrounding countryside.
Can I find long-stay vacation rentals in Castiglion Fiorentino?
A long-stay vacation rental in Castiglion Fiorentino is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Castiglion Fiorentino?
In Castiglion Fiorentino, there are numerous pet-friendly house rentals available, with around 137 options to choose from. This charming town in Tuscany offers a variety of accommodations that cater to both you and your furry friends. Many of these rentals come equipped with essential amenities, such as fully equipped kitchens, outdoor spaces, and comfortable living areas, superb for a relaxing vacation.
Are there any remote work vacation rentals in Castiglion Fiorentino?
In Castiglion Fiorentino, there is a wide selection of remote work vacation rentals available, with around 207 options to choose from. This picturesque town in Tuscany offers a charming setting for those looking to combine work and leisure. Many of these properties come equipped with essential amenities for remote work, such as reliable Wi-Fi, dedicated office spaces with desks and chairs, and safes for securing valuables. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Castiglion Fiorentino vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Castiglion Fiorentino with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Castiglion Fiorentino?
In Castiglion Fiorentino, popular rental amenities include kitchens, allowing guests to prepare their own meals, and private pools for a refreshing dip in the warm Tuscan sun. Many properties also feature refrigerators, ensuring that travellers can store their perishables conveniently. Additionally, free Wi-Fi is commonly available, enabling guests to stay connected during their stay.
When is the best time to visit Castiglion Fiorentino for a vacation rental?
The best time to visit Castiglion Fiorentino for a vacation rental is during the peak season from July to September. This vibrant period attracts travellers eager to immerse themselves in the stunning landscapes and rich culture of Tuscany. With warm temperatures averaging around 30°C, it's an ideal time for outdoor activities such as hiking through the picturesque hills or exploring the charming streets of the town.

July, in particular, stands out as the most popular month, where visitors can enjoy local festivals, outdoor markets, and delightful al fresco dining experiences. The atmosphere is lively, with both locals and tourists taking full advantage of the season's offerings.

For those seeking a more tranquil experience, consider visiting in November. This month offers a unique charm, as the tourist crowds thin out, allowing for a relaxed exploration of the area. You can still enjoy the beautiful Tuscan scenery, perhaps indulging in wine tours or cooking classes without the hustle and bustle.
How early should I book a Castiglion Fiorentino vacation rental?
Book your Castiglion Fiorentino vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Castiglion Fiorentino?
In Castiglion Fiorentino, visitors can engage in a rich tapestry of history and culture, with the charming medieval town centre being a highlight. The historic fortress, known as the Cassero, offers stunning panoramic views of the Val di Chio valley, making it a superb spot for photographs and leisurely strolls. Nearby, the picturesque Piazza del Municipio is lined with delightful cafes and shops, where vacation rentals often provide convenient access to local amenities.
Can I change or cancel my Castiglion Fiorentino home rental booking on Vrbo?
To find Castiglion Fiorentino vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Castiglion Fiorentino vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Vacation Rental options in Castiglion Fiorentino
Vacation rentals with pool in Castiglion Fiorentino
Standard Link for Castiglion Fiorentino
Ski vacation rentals in Castiglion Fiorentino
Standard Link for Castiglion Fiorentino
Oceanfront vacation rentals in Castiglion Fiorentino
Standard Link for Castiglion Fiorentino
Monthly rentals in Castiglion Fiorentino
Standard Link for Castiglion Fiorentino
Beach vacation rentals in Castiglion Fiorentino
Standard Link for Castiglion Fiorentino
Family-friendly vacation rentals in Castiglion Fiorentino
Standard Link for Castiglion Fiorentino
Mountain vacation rentals in Castiglion Fiorentino
Standard Link for Castiglion Fiorentino
Pet-friendly vacation rentals in Castiglion Fiorentino
Standard Link for Castiglion Fiorentino
Vacation rentals with hot tub in Castiglion Fiorentino
Standard Link for Castiglion Fiorentino
Lake vacation rentals in Castiglion Fiorentino
Standard Link for Castiglion Fiorentino

More Vacation Rentals ideas

Impruneta Vacation Rentals
Standard Link for Impruneta
San Gimignano Vacation Rentals
Standard Link for San Gimignano
Radda in Chianti Vacation Rentals
Standard Link for Radda in Chianti
Arezzo Vacation Rentals
Standard Link for Arezzo
Pergine Valdarno Vacation Rentals
Standard Link for Pergine Valdarno
Piombino Vacation Rentals
Standard Link for Piombino
Forte dei Marmi Vacation Rentals
Standard Link for Forte dei Marmi
Montepulciano Vacation Rentals
Standard Link for Montepulciano
Greve in Chianti Vacation Rentals
Standard Link for Greve in Chianti
Grosseto Vacation Rentals
Standard Link for Grosseto
Montalcino Vacation Rentals
Standard Link for Montalcino
Marciana Marina Vacation Rentals
Standard Link for Marciana Marina
Volterra Vacation Rentals
Standard Link for Volterra
Livorno Vacation Rentals
Standard Link for Livorno
Pienza Vacation Rentals
Standard Link for Pienza
Siena Vacation Rentals
Standard Link for Siena
Florence Vacation Rentals
Standard Link for Florence
Pisa Vacation Rentals
Standard Link for Pisa
Cortona Vacation Rentals
Standard Link for Cortona
Lucca Vacation Rentals
Standard Link for Lucca

People also search for

Florence Villas
Standard Link for Florence
San Gimignano Villas
Standard Link for San Gimignano
Florence Cottages
Standard Link for Florence
Siena Villas
Standard Link for Siena
Montalcino Villas
Standard Link for Montalcino
Lucca Villas
Standard Link for Lucca
Arezzo Villas
Standard Link for Arezzo
Florence Apartments
Standard Link for Florence
Montepulciano Villas
Standard Link for Montepulciano
Cortona Villas
Standard Link for Cortona