Castiglion Fiorentino vacation rentals

We found 2,330 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Castiglion Fiorentino by choosing from 95 houses, 33 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:Aug 22 - Aug 29
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Find out more about Castiglion Fiorentino

Find out more about Castiglion Fiorentino

Why visit Castiglion Fiorentino

  1. Historical Landmarks: Visit the impressive Cassero Tower and the archaeological museum to immerse yourself in the town's rich history.
  2. Charming Piazzas: Stroll through picturesque piazzas and churches that showcase the local architecture and culture.
  3. Stunning Landscapes: Enjoy breathtaking views of the Tuscan countryside, perfect for photography and relaxation.
  4. Outdoor Activities: Engage in outdoor adventures, from hiking trails to exploring nearby towns, ideal for families and couples.
  5. Vibrant Atmosphere: Experience the lively energy of the high season with festivals and local events that celebrate Tuscan culture.

Top attractions near Castiglion Fiorentino

Castiglion Fiorentino, nestled in Tuscany, is perfect for outdoor, romantic, and culture-themed vacations. Explore local attractions like the Cassero Tower, the archaeological museum, and charming piazzas and churches. This destination is ideal for families and culture seekers alike, offering a rich blend of history and city life. Don't forget to check traveler reviews and consider a day trip to fully immerse yourself in this picturesque town.

  1. Villa Bramasole: This historic villa, located 6 miles from Castiglion Fiorentino, offers a glimpse into the rich cultural heritage of Tuscany. Surrounded by beautiful landscapes, it exudes charm and tranquility, making it a perfect spot for relaxation and exploration.
  2. Piazza Grande: Situated 9 miles away, this vibrant square is the heart of local life, filled with cafes, shops, and stunning architecture. It's an ideal place to soak in the culture and enjoy the lively atmosphere of the city.
  3. Eremo Le Celle: Just 5 miles from Castiglion Fiorentino, this serene church is nestled in nature, providing a peaceful retreat. Its historical significance and tranquil surroundings make it a must-visit for those seeking spiritual reflection.

Things to do recommended for couples

Experience romance in Castiglion Fiorentino by playing tennis at the luxurious Tennis Club Castiglionese, savoring fine wines at Agricola Buccelletti Winery, and indulging in wellness treatments at San Giovanni Terme Rapolano, only 17 miles away. Your couple's getaway will be unforgettable!

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

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to apply the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Castiglion Fiorentino with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Castiglion Fiorentino with young kids: Traveling with young children can be quite demanding. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private swimming 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, a family vacation isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer amenities like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Castiglion Fiorentino: If you're in search of vacation rentals that offer discounts 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 rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Castiglion Fiorentino

Castiglion Fiorentino offers an enchanting blend of history, culture, and romance, making it a perfect destination for your vacation. Explore charming streets filled with art and soak in the stunning landscapes of Tuscany. Nearby towns provide a relaxed, welcoming atmosphere, ideal for a romantic getaway or a peaceful retreat. Experience the high season's vibrant energy while enjoying a wonderful stay in this picturesque region.

  • Cortona: Nestled about 6 miles from Castiglion Fiorentino, Cortona is a charming hilltop city that captivates visitors with its blend of outdoor beauty and rich cultural experiences. The city is renowned for its romantic ambiance, making it a perfect destination for couples. Explore the stunning landscapes and historic landmarks, including ancient bridges and picturesque lakes. Don’t miss the opportunity to indulge in a relaxing spa day or enjoy a performance at the local theater, offering a glimpse into the vibrant arts scene.
  • Arezzo: Located approximately 9 miles from Castiglion Fiorentino, Arezzo is a city steeped in history and culture. Travelers flock to Arezzo for its vibrant arts, outdoor activities, and romantic settings. The city boasts remarkable historic sites and beautiful piazzas that invite exploration. Enjoy a rejuvenating spa experience or catch an event at the arena entertainment facility. Arezzo's rich tapestry of history is evident in every corner, making it a fascinating stop on your Tuscan journey.
  • Montecchio: Situated close to Castiglion Fiorentino, Montecchio is a quaint village offering a delightful mix of culture and entertainment. With its charming atmosphere, Montecchio is ideal for those seeking a romantic getaway. The village is known for its educational venues and captivating historic sites, including ancient bridges that tell tales of the past. Wander through its scenic streets and soak in the local culture, making it a lovely addition to your Tuscany itinerary.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancy
January39.2°F (4.0°C)Light RainMostly CloudyAverage
February41.2°F (5.1°C)Light RainMostly SunnyAverage
March46.0°F (7.8°C)Light RainMostly SunnyAverage
April52.7°F (11.5°C)Light RainMostly SunnySlightly High
May59.5°F (15.3°C)Light RainMostly SunnyAverage
June69.1°F (20.6°C)Light RainMostly SunnyAverage
July74.8°F (23.8°C)No Rain (Dry)SunnySlightly High
August74.5°F (23.6°C)No Rain (Dry)SunnySlightly High
September65.7°F (18.7°C)Light RainMostly SunnyAverage
October56.8°F (13.8°C)Light RainMostly SunnySlightly Low
November48.6°F (9.2°C)Light RainMostly SunnySlightly Low
December41.7°F (5.4°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? One great way to do this is by being flexible with your travel dates, as prices can vary significantly. Additionally, booking an extended stay often leads to substantial discounts. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your needs!

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on the full booking amount. Being the planner truly has its benefits! When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash™ on eligible bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your trips, revisit your previous journeys, or organize your future plans. You can easily access properties you've saved or booked, which are now categorized under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

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)
  • 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)
  • Cantina Contucci (18.6 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 is the best area to stay in Castiglion Fiorentino when booking a vacation rental?
Podere Viti is among the most desired locations to book a vacation home in Castiglion Fiorentino. Base yourself here to savor the comfort and privacy that comes with having a place to yourself.
What is the most popular type of vacation rental accommodation in Castiglion Fiorentino?
Villas are the most popular kind of vacation rental in Castiglion Fiorentino, according to our data. Even if you have something bigger or smaller in mind, Vrbo has vacation homes in a variety of sizes and shapes. Take a look at our options to find your perfect fit.
How much does it cost to rent a vacation rental in Castiglion Fiorentino?
The average price for a vacation rental in Castiglion Fiorentino depends on a number of factors, including property type, length of stay and season. Whether you prefer a villa with space for extended family or a cozy cabin for just you and your sweetheart, just enter your travel dates to see stays with unbeatable value.
How much does it cost to rent a beach house in Castiglion Fiorentino?
When you travel and the style and size of the property will influence the cost of your beachside escape. Type in your Castiglion Fiorentino travel dates to view your available options on Vrbo. Can’t live without a private pool? Use the filters to select the features and amenities you want.
Are there pet-friendly vacation rentals in Castiglion Fiorentino?
With 259 vacation rentals that host pets, your furry best friend can join you on your Castiglion Fiorentino getaway. Use the filter tool to search our pet-friendly vacation rentals and find a stay that’s pawfect on Vrbo.
Can I rent a house with a pool in Castiglion Fiorentino?
Pack your swimsuit and inflatable unicorn, because there are 226 houses with a private pool in Castiglion Fiorentino. Make a booking at one of these superb vacation rentals and let every day be a pool day. Simply enter your travel dates into Vrbo, then check the “pool” filter to find the ideal place for a splashing good time!
What are popular rental amenities in Castiglion Fiorentino?
The most popular rental amenities people search for in Castiglion Fiorentino are a barbecue grill, tennis and a nearby waterfront. Whether you’re taking a trip with your besties, family or even pets, Vrbo vacation homes include the best amenities for making epic memories with the people that matter most.
Are there large group vacation rentals in Castiglion Fiorentino?
Choose from 94 vacation homes in Castiglion Fiorentino that can sleep 10 or more people. Whether you’re planning a get-together with extended family or some kind of special event, there’s enough space to get your loved ones together under one roof.
Are there vacation rentals in Castiglion Fiorentino that welcome kids?
With 253 family-friendly vacation rentals available in Castiglion Fiorentino, now is a superb time to introduce your kids to the wonders of travel. Click on our “Properties good for families” filter box to find stays that come with conveniences ideal for vacationing families, such as kitchens, swimming pools, bunk beds and entertainment areas.
What are the top attractions for families in Castiglion Fiorentino?
Keep the kids busy at these popular family-friendly attractions in Castiglion Fiorentino:

  • Cassero Tower
  • Municipal Art Gallery
  • Archaeological Museum

Are there one-bedroom vacation rentals in Castiglion Fiorentino?
Yes, there are 37 one-bedroom properties in Castiglion Fiorentino to choose from. A one-bedroom vacation property is a wonderful choice if it’s just the two of you or if you’re traveling alone. Throw in more space, privacy and convenience compared to a hotel, and you’ll be sure to have a memorable getaway.
Can I find two-bedroom vacation rentals in Castiglion Fiorentino?
Take off with your besties and relax in total privacy and comfort in one of the 60 two-bedroom vacation rentals Castiglion Fiorentino has to offer.
Are there vacation rentals with WiFi in Castiglion Fiorentino?
Take your pick of 77 vacation rentals with WiFi in Castiglion Fiorentino. If you’d like to disconnect from daily life on your vacation, but still need to be connected to the web, these properties have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Castiglion Fiorentino?
You’ll find 138 Vrbo vacation rentals with air conditioning in Castiglion Fiorentino giving you that cool, cool breeze and extra touch of comfort. Enter your preferred travel dates and then make use of our filters to help you find stays with air conditioning.
How old do you have to be to rent a vacation rental in Castiglion Fiorentino?
The age limit can differ between properties on Vrbo, so be sure to look at the rules of the vacation rental in Castiglion Fiorentino you’re interested in. But typically, it’s 16, 18 or 21.
How long can I rent a vacation rental in Castiglion Fiorentino for?
The length of time you can rent a vacation rental in Castiglion Fiorentino is up to the property. Just enter your chosen travel dates to view a list of options offering extended stays. With a range of creature comforts like laundries and air conditioning, as well as some offering weekly or monthly discounts, you’re sure to find the perfect place to call your home away from home in Castiglion Fiorentino.
Does Vrbo offer discounts for vacation homes in Castiglion Fiorentino?
On Vrbo, we’ve got some great bargains and discounts for Castiglion Fiorentino. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re planning a short getaway or an extended escape, Vrbo has a variety of options for all budgets and styles.

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