Photo by Vanessa Sgaravizzi

Castelfiorentino holiday lettings

We found 193 holiday rentals — enter your dates for availability

Select from 41 houses, 46 apartments and other holiday rentals to find the perfect place for your stay in Castelfiorentino. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, including parking and a TV. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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The rustic city of Castelfiorentino awaits you

Enjoy the area's theatre scene, wineries and monuments with a rental holiday home in Castelfiorentino. This scenic and welcoming city entices travellers with its restaurants and gardens. Uffizi Gallery and Cathedral of Santa Maria del Fiore are just a couple of the must-see attractions in the area. 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 and around Castelfiorentino

Are you looking for attractions to see in the area? Venture out of your holiday home and experience everything that makes Castelfiorentino a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Castelfalfi Golf Course (7.2 mi / 11.5 km)
  • Tenuta Torciano Winery (8.6 mi / 13.8 km)
  • Sovestro in Poggio Winery (10.9 mi / 17.6 km)
  • Antinori nel Chianti Classico (11.1 mi / 17.9 km)
  • Golf Club Bellosguardo Vinci (11.2 mi / 18.1 km)
  • Castello di Monsanto (13.4 mi / 21.5 km)

Exploring the natural landscape of Castelfiorentino

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

  • Sentierelsa Trail (14.9 mi / 23.9 km)
  • Cascine Park (17.3 mi / 27.9 km)
  • Boboli Gardens (17.7 mi / 28.5 km)
  • Arno River (18.3 mi / 29.4 km)
  • Casciana Thermal Baths (18.4 mi / 29.6 km)
  • Renai Park (14 mi / 22.5 km)

How to get to and around Castelfiorentino

The nearest airport is in Peretola Airport (FLR), located 17.9 mi (28.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Pisa (PSA-Galileo Galilei), which is 29.2 mi (47 km) away.

If you'd prefer to travel by train, the main station serving the city is Castelfiorentino Station.

Frequently asked questions

What is the best area to stay in Castelfiorentino when booking a holiday rental?
When considering a holiday rental in Castelfiorentino, a popular area to stay is the historic centre. This charming district is characterised by its medieval architecture, narrow streets, and vibrant atmosphere. Staying here places you within easy reach of top attractions such as the stunning Church of SS. Maria e Giovanni, renowned for its beautiful frescoes and peaceful ambience. You can also explore the local shops and cafes, which offer a taste of authentic Tuscan life.

Another appealing area is the outskirts of Castelfiorentino, where you can find a mix of rustic charm and stunning countryside views. This region is superb for those looking to enjoy the tranquillity of the Tuscan landscape while still being close to the town's amenities. You may find a variety of properties, from traditional villas to modern apartments, allowing for a comfortable and enjoyable stay.
How much does it cost to rent a holiday home in Castelfiorentino?
Prices for holiday rentals in Castelfiorentino 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 Castelfiorentino 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 Castelfiorentino holiday house rentals?
You can find great discounts on house rentals in Castelfiorentino 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 holiday rental accomodation in Castelfiorentino?
In Castelfiorentino, holiday houses are the most popular type of rental accommodation, with approximately 38 available in the area. These holiday houses offer spacious living arrangements, often featuring multiple bedrooms, fully equipped kitchens, and private outdoor spaces such as gardens or terraces, superb for enjoying the beautiful Tuscan countryside. Additionally, there are about 35 apartments scattered throughout the town, providing a more compact and convenient option for smaller groups or couples. These apartments typically include modern amenities, cosy living areas, and easy access to local shops and restaurants. Furthermore, around 32 villas can be found in this charming region, often characterised by luxurious features, private pools, and stunning views of the surrounding landscape. Lastly, there are several cottages available, offering a quaint and rustic feel for those seeking a peaceful retreat.
Are there any family house rentals in Castelfiorentino?
In Castelfiorentino, Tuscany, there is a wealth of family-friendly house rentals available, with around 66 options to choose from. This charming town, known for its beautiful landscapes and rich history, offers properties in various neighbourhoods that cater to families seeking a memorable stay. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play and explore.
Can I rent a holiday home with a pool or hot tub in Castelfiorentino?
In Castelfiorentino, Tuscany, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 104 options to choose from. This picturesque town, located in the heart of the Tuscan countryside, provides a serene backdrop for travellers seeking relaxation. Many of these properties are situated in scenic locations, offering stunning views of the surrounding vineyards and olive groves.
Can I find long-stay holiday rentals in Castelfiorentino?
A long-stay holiday rental in Castelfiorentino 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 Castelfiorentino?
In Castelfiorentino, there are numerous pet-friendly house rentals available, with about 51 options to choose from. This charming town, located in the heart of Tuscany, offers a delightful blend of rustic beauty and modern amenities. Many of these holiday homes feature spacious gardens, outdoor seating areas, and fully equipped kitchens, making them ideal for families or groups travelling with pets.
Are there any remote work holiday rentals in Castelfiorentino?
In Castelfiorentino, Tuscany, there are plenty of remote work holiday rentals available, with around 105 options to choose from. This picturesque town, located between Florence and Siena, offers a tranquil environment that is ideal for working remotely while enjoying the beauty of the Tuscan countryside. Many of these properties come equipped with essential amenities such as desks, Wi-Fi, and comfortable desk chairs, allowing for a productive work-from-home experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Castelfiorentino holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Castelfiorentino 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 Castelfiorentino?
In Castelfiorentino, holiday rentals commonly feature amenities that enhance the comfort and convenience of guests. Many properties include well-equipped kitchens, allowing travellers to prepare their own meals, which is particularly appealing for those wanting to experience local produce. Shared pools are also a popular amenity, providing a refreshing spot to relax and socialise on warm days. Additionally, free Wi-Fi is typically available in many accommodations, ensuring guests can stay connected during their stay. Some rentals may also come with dishwashers, making clean-up after meals effortless.
How early should I book a Castelfiorentino holiday rental?
Book your Castelfiorentino holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Castelfiorentino?
In Castelfiorentino, visitors can take part in the rich culture and history of Tuscany. The town's historic centre features charming medieval architecture and is home to top sites such as the Church of Santa Maria dell'Assunta, which boasts beautiful frescoes and a tranquil atmosphere.

The surrounding countryside offers stunning views and opportunities for outdoor activities, with vineyards and olive groves characterising the landscape. For those interested in local cuisine, the area has excellent eateries where one can sample traditional Tuscan dishes made from fresh, local ingredients.
Can I change or cancel my Castelfiorentino home rental booking on Vrbo?
To find Castelfiorentino holiday 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 Castelfiorentino holiday 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.

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