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Castiglion Fiorentino vacation rentals

We found 2,190 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Castiglion Fiorentino by choosing from 64 houses, 25 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:Jun 12 - Jun 19

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Property grounds
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Apartment in Farmhouse

Cortona

6% off
Price is $156
$1,091 for 7 nights
All fees included
Apartment in Farmhouse

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Find out more about Castiglion Fiorentino

Why visit Castiglion Fiorentino

  • Rich cultural heritage: Discover charming churches, lively piazzas, and stunning cathedrals that reflect Tuscany's artistic essence.
  • Outdoor adventures: Enjoy picturesque landscapes ideal for hiking and romantic strolls in the countryside.
  • Inviting accommodations: Choose from cozy villas, private homes, and apartments with pools and essential amenities.
  • Local cuisine: Savor authentic Italian dishes that showcase the region's culinary delights.
  • Welcoming community: Experience the warmth of friendly locals who enhance your travel experience.

Popular types of accommodation in Castiglion Fiorentino

If you're exploring vacation rentals in Castiglion Fiorentino, you're in for a treat. The most sought-after accommodations include charming villas, cozy houses, and comfortable apartments. Many options feature inviting swimming pools, essential room amenities, guest houses for extra space, complimentary Wi-Fi, and delightful breakfast offerings. Enjoy a relaxing getaway with all the comforts of home in this enchanting Italian town.

  • Villas: The top choice for vacation rentals in Castiglion Fiorentino, offering spacious accommodations and luxurious amenities.
  • Houses: A popular option for families and groups, providing a home-like atmosphere with all the comforts.
  • Apartments: Ideal for couples or solo travelers, these cozy spaces allow for a more intimate experience.
  • Cottages: Charming and quaint, perfect for those seeking a peaceful retreat in the countryside.
  • Agritourism: Experience authentic Tuscan life while enjoying farm stays in picturesque settings.**

Top attractions near Castiglion Fiorentino

Castiglion Fiorentino is perfect for outdoor enthusiasts and those seeking a romantic getaway steeped in culture. Explore charming churches, lively piazzas, and stunning cathedrals that capture the essence of this beautiful Tuscan town. Whether traveling solo, with family, or as a couple, you'll find a variety of attractions that cater to your desire for rich cultural experiences and memorable moments in this enchanting destination.

  • Villa Bramasole: This historic villa, located 6 miles from Castiglion Fiorentino, offers a glimpse into Tuscan culture and history. Its beautiful architecture and serene surroundings make it a perfect spot for relaxation and inspiration.
  • Piazza Grande: Situated 9 miles away, this vibrant square is the heart of the city, filled with culture and lively atmosphere. Enjoy local cafés, artisan shops, and stunning architecture that captures the essence of Italian life.
  • Cortona Cathedral: Just 5 miles from Castiglion Fiorentino, this magnificent cathedral showcases rich history and artistic beauty. Its tranquil ambiance invites visitors to explore its impressive interior and admire the surrounding views.

Things to do recommended for couples

For a romantic getaway in Castiglion Fiorentino, indulge in luxury at the Tennis Club Castiglionese, savor exquisite wines at Agricola Buccelletti Winery, and unwind at San Giovanni Terme Rapolano, only 17 miles away, for a blissful wellness experience. Perfect for couples seeking unforgettable memories.

Things to do recommended for families

In Castiglion Fiorentino, families can explore the stunning outdoor parks, enjoy a fun-filled day at the local animal farm, or take part in cooking classes to learn traditional Tuscan recipes. The charming streets and local markets also offer delightful experiences for both kids and adults.

Things to do recommended for groups

Explore the Valdichiana Outlet Village for a fun shopping experience, catch a show at the charming Signorelli Theatre, or enjoy a round of golf at the scenic Golf Club Valdichiana. Each offers unique vibes perfect for group bonding in beautiful Tuscany.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Castiglion Fiorentino

If you’re traveling with a group, family, or pets, or planning an extended stay, be sure to use the appropriate filters to prioritize your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Castiglion Fiorentino with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Castiglion Fiorentino with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Castiglion Fiorentino: For many families, a trip isn't truly fulfilling without their beloved pet by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly homes come equipped with feeding bowls and cozy beds, ensuring that all members of the family feel comfortable and at ease.
  • Planning for a long term stay visiting Castiglion Fiorentino: If you're in search of vacation rentals with great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Castiglion Fiorentino

Castiglion Fiorentino offers a delightful getaway for travelers seeking a mix of outdoor adventures and rich culture. With its rustic charm and breathtaking views, this enchanting city invites you to explore its historical sites and enjoy the warmth of Italian hospitality. Nearby neighborhoods provide a relaxing atmosphere perfect for romantic strolls, while the friendly locals enhance your experience. Whether you're wandering through ancient streets or savoring local cuisine, Castiglion Fiorentino promises an unforgettable vacation.

  • Cortona: Nestled approximately 6 miles from Castiglion Fiorentino, Cortona is a charming hilltop city that offers a delightful blend of outdoor and cultural experiences. Known for its romantic ambiance, visitors can explore serene landscapes, historic sites, and enjoy wellness treatments at local spas. Key attractions include the picturesque lake, ancient bridges, and the historic town center, where you can immerse yourself in the rich history and art that this beautiful Tuscan city has to offer.
  • Arezzo: Located about 9 miles from Castiglion Fiorentino, Arezzo is a vibrant city steeped in culture and history. This destination is perfect for those seeking romantic outings and outdoor adventures. The city boasts a variety of activities, from refreshing spa services to thrilling arena events. Don’t miss the chance to visit historic sites, including stunning piazzas and landmarks that showcase Arezzo's artistic heritage, making it a must-see for culture enthusiasts.
  • La Strada-Santa Cristina: Just a stone’s throw from Castiglion Fiorentino, La Strada-Santa Cristina is a quaint village known for its engaging outdoor and entertainment-themed experiences. This enchanting locale offers unique activities like horseracing and lively musicals that will captivate visitors. Explore the local historic house and visitor center to uncover the village's past, and enjoy the romantic charm that this small community exudes, making it a perfect spot for a delightful day trip.

Best time to go to Castiglion Fiorentino

If you're planning a trip to Castiglion Fiorentino, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and July to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January39.2°F (4.0°C)Light RainMostly CloudyAverageAverage
February41.2°F (5.1°C)Light RainMostly SunnyAverageSlightly Low
March46.0°F (7.8°C)Light RainMostly SunnyAverageSlightly Low
April52.7°F (11.5°C)Light RainMostly SunnySlightly HighAverage
May59.5°F (15.3°C)Light RainMostly SunnyAverageAverage
June69.1°F (20.6°C)Light RainMostly SunnyAverageSlightly High
July74.8°F (23.8°C)No Rain (Dry)SunnySlightly HighSlightly High
August74.5°F (23.6°C)No Rain (Dry)SunnySlightly HighSlightly High
September65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
October56.8°F (13.8°C)Light RainMostly SunnySlightly LowAverage
November48.6°F (9.2°C)Light RainMostly SunnySlightly LowSlightly Low
December41.7°F (5.4°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save money on your next adventure? Being flexible with your travel dates can be a great strategy, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that meets your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect fit for your getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner truly has its perks. By enrolling in our travel rewards program, One Key, you can immediately access member discounts and accumulate OneKeyCash on eligible reservations. Sign up today and begin reaping the savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly area to plan new trips, continue from where you last stopped, or manage your travel arrangements. You can easily see the properties you’ve saved or reserved, organized into categories such as Potential, Upcoming, and Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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:

  • Fattoria Le Capezzine (11.6 mi / 18.7 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:

  • Sandro Pertini Park (8.2 mi / 13.3 km)
  • 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)

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, Tuscany, Italy when booking a vacation rental?
When considering a vacation rental in Castiglion Fiorentino, a popular area to stay is in the historic center. This charming neighborhood offers a unique blend of medieval architecture and modern amenities, allowing visitors to immerse themselves in the rich cultural heritage of Tuscany. The narrow streets are lined with quaint shops, delightful cafes, and local restaurants, providing plenty of options for dining and shopping.

In the historic center, you'll find remarkable attractions such as the ancient fortress, which offers stunning panoramic views of the surrounding countryside, and the beautiful Church of Sant'Angelo, known for its impressive frescoes. Another highlight is the lovely public gardens, superb for a leisurely stroll or a picnic.

While the number of properties in this area can vary, you can typically find a selection of charming apartments and villas that reflect the traditional Tuscan style. Staying here not only places you in the heart of the town but also provides easy access to local events and festivals that celebrate the vibrant culture of the region.
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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
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 98 available throughout the picturesque Tuscan countryside. These spacious properties often feature elegant designs, private gardens, and outdoor terraces, allowing guests to enjoy the stunning views of the surrounding landscape. Many villas come equipped with modern kitchens, comfortable living areas, and amenities such as swimming pools, making them great for families or groups seeking a relaxing getaway.

Vacation houses are also quite popular, with approximately 69 options scattered in and around the town. These homes typically provide a cozy atmosphere, multiple bedrooms, and outdoor spaces ideal for dining al fresco while soaking in the serene Tuscan ambiance. Additionally, there are about 23 apartments available, mostly situated within the charming town center, offering easy access to local shops and restaurants. These apartments generally include essential amenities like fully equipped kitchens and comfortable living spaces.

Lastly, there are several cottages available, which provide a quaint and rustic charm, often set in more secluded areas.
Are there any family house rentals in Castiglion Fiorentino?
In Castiglion Fiorentino, Tuscany, there are numerous family-friendly house rentals available, totaling around 98 options. This charming town offers a picturesque setting with its rich history and beautiful landscapes, making it an ideal destination for families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play or enjoy al fresco dining.

Visitors can explore local attractions such as the historic town center, which is home to ancient architecture and quaint shops, as well as nearby parks that provide opportunities for outdoor activities. Additionally, the surrounding region of Tuscany is famous for its stunning countryside and vineyards, superb for family outings and day trips.
Can I rent a vacation home with a pool or hot tub in Castiglion Fiorentino?
In Castiglion Fiorentino, visitors can find a variety of vacation homes available for rent that come equipped with pools or hot tubs, with around 167 options to choose from. This charming town in Tuscany offers a picturesque setting with beautiful countryside views, making it a delightful destination for relaxation. Many of these properties feature private pools, outdoor hot tubs, and spacious gardens, superb for enjoying the serene Tuscan landscape.

Travelers can expect amenities such as fully equipped kitchens for preparing meals, cozy living areas for family gatherings, and outdoor dining spaces to enjoy al fresco meals. Additionally, some rentals offer proximity to local attractions, vineyards, and historical sites, allowing guests to immerse themselves in the rich culture and beauty of the region while having a comfortable retreat to return to after a day of exploration.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Castiglion Fiorentino?
In Castiglion Fiorentino, travelers can find a variety of pet-friendly house rentals, with over a hundred options available. This charming town in Tuscany offers accommodations that often feature traditional Italian architecture, spacious gardens, and outdoor dining areas, making it ideal for families and pet owners. Many properties come equipped with modern amenities such as fully equipped kitchens, Wi-Fi, and comfortable living spaces, allowing guests to relax and feel at home during their stay.

The surrounding countryside provides ample opportunities for outdoor activities with pets, including scenic walks through the rolling hills and vineyards. Nearby points of interest, such as the beautiful Val di Chiana region, invite exploration and adventure, adding to the overall experience.
Are there any remote work vacation rentals in Castiglion Fiorentino?
In Castiglion Fiorentino, there are ample options for remote work vacation rentals, with around 174 properties available. This charming town in Tuscany offers a picturesque setting for those looking to blend work and leisure. Many of the rentals come equipped with essential amenities such as free Wi-Fi, dedicated workspaces or desks, and comfortable living areas, making it easy to maintain productivity while enjoying the beauty of the Italian countryside.

You can expect to find a variety of accommodations, from rustic villas to modern apartments, often featuring nice views of the surrounding hills and vineyards. The town itself is rich in history, with local attractions like the historic castle and quaint piazzas, providing a delightful backdrop for your stay. Additionally, the culinary scene in Castiglion Fiorentino is vibrant, with many opportunities to enjoy traditional Tuscan dishes at nearby restaurants. 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 travelers 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 vacation rental amenities include kitchens, which allow travelers to prepare their own meals and enjoy the local cuisine. Many rentals also offer onsite parking, making it convenient for those who prefer to drive and explore the beautiful Tuscan countryside. A private pool is a sought-after feature, great for relaxing and enjoying the warm Italian weather. Additionally, many properties come equipped with fireplaces, adding a cozy touch for cooler evenings. For those traveling with pets, it's common to find rentals that permit pets, ensuring that furry companions can join the trip.
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 travelers eager to soak up the sun and immerse themselves in the rich culture of Tuscany. With warm temperatures averaging in the mid-80s Fahrenheit, the weather is great for outdoor activities such as exploring the historic streets, enjoying local cuisine at al fresco dining spots, and taking in the stunning landscapes that define this picturesque region.

July stands out as the most popular month, drawing visitors who relish the lively option. The town comes alive with summer festivals, art exhibitions, and opportunities to engage with the local community. It's an ideal time for sightseeing, as the longer days allow you to explore both Castiglion Fiorentino and nearby cities like Arezzo and Cortona at a leisurely pace.

For those considering a budget-friendly option, November offers a unique charm with fewer crowds. Although the temperatures can drop to the low 50s Fahrenheit, this tranquil month showcases the beautiful fall colors and allows for a more intimate experience of the town's historical sites without the bustling summer crowds.

Ultimately, your choice of when to visit Castiglion Fiorentino should reflect your preferences for a lively summer ambiance or a peaceful autumn retreat.
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, Tuscany, Italy?
In Castiglion Fiorentino, visitors can discover a range of attractions that highlight the town's rich history and charming Tuscan landscape. The historic center is a must-visit, featuring the medieval fortress known as the Cassero, which offers panoramic views of the surrounding countryside. Nearby, the Church of San Francesco showcases beautiful frescoes and is a significant cultural site.

Exploring the quaint streets, travelers can enjoy local shops and cafes, providing a taste of authentic Italian cuisine. Just a short distance from the town, the Etruscan ruins are a fascinating glimpse into the area's ancient past, while the nearby Val di Chio valley is great for those looking to soak in the stunning natural beauty of Tuscany.

For art lovers, the surrounding area is dotted with vineyards and olive groves, where visitors can partake in wine and olive oil tastings, enhancing their experience of the region.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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