Castiglion Fiorentino vacation rentals

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Nestled in the heart of Tuscany, the enchanting village of Castiglion Fiorentino invites you to wander its historic streets, where rustic charm meets vibrant culture. Immerse yourself in local traditions as you explore stunning churches, lively piazzas, and breathtaking landscapes that promise adventure. With a variety of spacious villas, cozy apartments, and family-friendly accommodations equipped with modern amenities, your group can relish the comforts of home while savoring the flavors of Tuscany, from wine tastings at Agricola Buccelletti to the serene beauty of nearby Cortona.

Holiday rentals with weekly discounts - Castiglion Fiorentino

Showing deals for:Dec 25 - Jan 1

Pool
Outdoor dining
Exterior detail
Dining
Exceptional
(6 reviews)

Apartment in Farmhouse

Cortona

6% off
$153
$1,072 for 7 nights
All fees included
Apartment in Farmhouse
Interior
Property grounds
Exterior
Outdoor dining
Exceptional
(37 reviews)

Villa Mulinoavento with magnificent view 5 minutes walking downtown

Cortona

9% off
$730
$5,113 for 7 nights
All fees included
Villa Mulinoavento with magnificent view 5 minutes walking downtown
The master bedroom promises privacy
There's no doubt you're in Tuscany
We've tailored every detail to help you feel at home
Welcome to a piece of history!
Exceptional
(24 reviews)

Medieval Delight! Balcony, Rustic Beams & Brick Fireplace w/Modern Amenities

Castiglion Fiorentino

9% off
$160
$1,123 for 7 nights
All fees included
Medieval Delight! Balcony, Rustic Beams & Brick Fireplace w/Modern Amenities
Living room + Sofa bed
View from the outside
entrance
Dining Room
Exceptional
(59 reviews)

Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"

Cortona

14% off
$246
$1,719 for 7 nights
All fees included
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Enter here
Interior
Relax in this cozy living area
AHHH!  Tuscany!
Exceptional
(11 reviews)

❤️ of Castiglion Fiorentino

Castiglion Fiorentino

8% off
$120
$838 for 7 nights
All fees included
❤️ of Castiglion Fiorentino
Exterior
Property grounds
Stalla Private Garden with BBQ
Living area
Exceptional
(19 reviews)

Large country apartment in Cortona 3bed3bath with shared pool & gorgeous gardens

Cortona

7% off
$491
$3,437 for 7 nights
All fees included
Large country apartment in Cortona 3bed3bath with shared pool & gorgeous gardens
Interior
Outdoor dining
Exterior detail
Room
Exceptional
(11 reviews)

My house with steam room, theater view, chromtherapy, relaxing music, jacuzzi...

Cortona

7% off
$204
$1,427 for 7 nights
All fees included
My house with steam room, theater view, chromtherapy, relaxing music, jacuzzi...
Pool
Outdoor dining
Exterior
Property grounds
Exceptional
(25 reviews)

Farm on the hills of Cortona with a spectacular view of the Valdichiana Valley

Cortona

7% off
$255
$1,786 for 7 nights
All fees included
Farm on the hills of Cortona with a spectacular view of the Valdichiana Valley
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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.

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:

  • Tennis Club Castiglionese (0.3 mi / 0.5 km)
  • Terme Antica Querciolaia (16.3 mi / 26.2 km)
  • San Giovanni Terme Rapolano (17.2 mi / 27.7 km)
  • Il Borro Wines (17.3 mi / 27.8 km)
  • Villa a Sesta Polo Club (18.3 mi / 29.5 km)
  • Consorzio del Vino Nobile di Montepulciano (18.7 mi / 30 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)
  • Terme Antica Querciolaia (16.3 mi / 26.2 km)
  • Lake Trasimeno (17 mi / 27.3 km)
  • Val di Chiana (18.6 mi / 30 km)
  • Terme di Montepulciano Spa (19.5 mi / 31.4 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 are the best areas to stay in a vacation rental in Castiglion Fiorentino?
Castiglion Fiorentino offers a variety of vacation rentals throughout the city, providing space, privacy, and room to settle in comfortably for all types of guests. You'll find over 210 vacation rentals, with houses and villas being the most common property types. These options cater to families, groups, and couples looking for a relaxing stay in the Tuscan countryside. Many rentals are conveniently located within a short walk or drive of central attractions like Cassero Tower and Vasari Loggia, making it easy to explore the town's historic charm.
What are the most popular vacation rentals in Castiglion Fiorentino?
The most sought-after vacation rentals in Castiglion Fiorentino are houses and villas. You'll find over 80 houses and over 80 villas available, offering ample space and privacy, making them ideal for families and groups. Apartments are also a popular choice, with around 20 available, often providing a convenient base for exploring the town. For a more charming and intimate experience, there are also several cottages to choose from.
What amenities do vacation rentals in Castiglion Fiorentino usually offer?
Vacation rentals in Castiglion Fiorentino typically offer a range of amenities designed for a comfortable stay. You can expect fully equipped kitchens, laundry facilities, and climate control to ensure a pleasant environment. Many properties also include a television for entertainment, outdoor areas like patios or yards, and balconies or terraces to enjoy the Tuscan views. Free parking is commonly available, and a significant number of rentals feature pools for relaxation.
Are there family-friendly vacation rentals in Castiglion Fiorentino?
Yes, Castiglion Fiorentino provides over 100 family-friendly vacation rentals, making it easy to plan a trip with children. Houses and villas are the most common property types, offering plenty of space for everyone. These rentals often come with amenities that cater to families, such as fully equipped kitchens for preparing meals, laundry facilities, and travel cribs or high chairs for younger guests. Many also feature outdoor play areas or barbecue grills for family enjoyment.
Are there pet-friendly vacation rentals in Castiglion Fiorentino?
Yes, you'll find over 130 pet-friendly vacation rentals in Castiglion Fiorentino, so your furry companions can join your Tuscan getaway. Villas and houses are the most common types of pet-friendly properties. Many of these rentals offer amenities like secured yards, providing a safe space for pets to play. With plenty of outdoor areas in the region, it's easy to find walking paths and enjoy the countryside with your pet.
What are the best areas for group vacation rentals in Castiglion Fiorentino?
Castiglion Fiorentino features over 100 vacation rentals well-suited for groups, offering ample space and amenities for a memorable shared experience. Houses and villas are the most prevalent property types, providing multiple bedrooms and bathrooms to accommodate larger parties. These rentals often include spacious outdoor areas for gathering, large kitchens for communal cooking, and plenty of parking for several vehicles, ensuring comfort and convenience for everyone.
What are the best luxury vacation rentals in Castiglion Fiorentino?
For a luxurious stay, Castiglion Fiorentino offers over 80 upscale vacation rentals, primarily in the form of elegant villas and spacious houses. These properties often come with premium amenities designed for comfort and indulgence. You can expect features like private pools, hot tubs for relaxation, and cozy fireplaces. Many also boast expansive balconies or terraces, perfect for enjoying the scenic Tuscan landscape in style.
Are there any budget-friendly vacation rentals in Castiglion Fiorentino?
Yes, Castiglion Fiorentino has over 80 budget-friendly vacation rentals, offering great value for your trip. Houses and cottages are often excellent choices for guests seeking affordability without compromising on comfort. These rentals typically include amenities like fully equipped kitchens, which can help save on dining costs, and laundry facilities. Many also provide free parking, adding to the overall value of your stay.
Are there any vacation rentals in Castiglion Fiorentino with a pool?
Yes, over 170 vacation rentals in Castiglion Fiorentino come with pools, providing a refreshing amenity for your stay. Villas and houses are the most common property types to feature pools. You'll find a variety of options, including private pools for enhanced privacy, outdoor pools perfect for enjoying the Tuscan sun, and some heated pools for cooler evenings.
Are there any vacation rentals in Castiglion Fiorentino with a hot tub?
Yes, around 30 vacation rentals in Castiglion Fiorentino feature a hot tub, offering a relaxing way to unwind after a day of exploring. Villas are the most common property type to include this amenity, with houses and apartments also offering options. These hot tubs are typically private, providing a serene setting for soaking and enjoying the peaceful surroundings.
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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