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San Casciano in Val di Pesa holiday lettings

We found 867 holiday rentals — enter your dates for availability

Discover a selection of 67 homes, 91 apartments and other holiday rentals in San Casciano in Val di Pesa that are perfect for your trip. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as parking and a washer and dryer. At the end of the day, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - San Casciano in Val di Pesa

Showing deals for:2 Jan - 9 Jan

Image gallery for Medieval Castle 15 km from Florence, in the heart of "Chianti Classico" region

Aerial view
10 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)

Medieval Castle 15 km from Florence, in the heart of "Chianti Classico" region

Greve in Chianti, Toscana

9% off
Price is £9,617
for 7 nights, 1 room
£1,374 per night
includes taxes & fees
Medieval Castle 15 km from Florence, in the heart of "Chianti Classico" region

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Find out more about San Casciano in Val di Pesa

Find out more about San Casciano in Val di Pesa

Relaxing San Casciano in Val di Pesa will entice you

Enjoy the wineries and other features of San Casciano in Val di Pesa. Well known for its cheese shops, spas and coffee shops, this relaxing city won't disappoint. Uffizi Gallery and Cathedral of Santa Maria del Fiore are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around San Casciano in Val di Pesa

Do you want to discover attractions to visit while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes San Casciano in Val di Pesa a fun spot to go on holiday. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Antinori nel Chianti Classico (3.2 mi / 5.2 km)
  • Villa Medicea di Lilliano - Malenchini (7.2 mi / 11.6 km)
  • Ruffino - Tenuta di Poggio Casciano (7.3 mi / 11.8 km)
  • Visarno Arena (8.7 mi / 14 km)
  • Casa Sola - Chianti Winery (9.5 mi / 15.2 km)
  • Buondonno Winery (10 mi / 16.1 km)

Exploring the natural landscape of San Casciano in Val di Pesa

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, San Casciano in Val di Pesa is a great place to spend some time outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Boboli Gardens (7.8 mi / 12.6 km)
  • Arno River (8.2 mi / 13.2 km)
  • Cascine Park (9 mi / 14.4 km)
  • Olmo (14.5 mi / 23.4 km)
  • Florence Botanical Gardens (9.1 mi / 14.6 km)
  • Villa di Castello (11.3 mi / 18.2 km)

Travelling to and around San Casciano in Val di Pesa

The nearest airport is in Peretola Airport (FLR), located 10 mi (16 km) from the city centre.

Frequently asked questions

What is the best area to stay in San Casciano In Val Di Pesa when booking a holiday rental?
When considering a holiday rental in San Casciano in Val di Pesa, the area surrounding the historic town centre is an excellent choice. This vibrant neighbourhood offers a delightful blend of classic Tuscan charm and modern amenities, making it an ideal base for your explorations. Staying here allows you to immerse yourself in the local culture, with quaint streets lined with shops, cafes, and restaurants that serve authentic Tuscan cuisine.

One of the top attractions nearby is the stunning Church of San Cassiano, which showcases beautiful frescoes and a peaceful atmosphere, superb for a moment of reflection. Additionally, the picturesque surroundings provide easy access to the renowned Chianti wine region, inviting you to indulge in wine tastings at local vineyards.
How much does it cost to rent a holiday home in San Casciano In Val Di Pesa?
Prices for holiday rentals in San Casciano In Val Di Pesa 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 San Casciano In Val Di Pesa 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 San Casciano In Val Di Pesa holiday house rentals?
You can find great discounts on house rentals in San Casciano In Val Di Pesa 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 San Casciano In Val Di Pesa?
In San Casciano In Val Di Pesa, apartments are the most popular type of holiday rental, with approximately 86 available throughout the charming town. These apartments typically feature fully equipped kitchens, comfortable living areas, and often delightful views of the surrounding Tuscan countryside. Many are situated near points of interest such as local wineries and historical sites, offering guests an authentic experience of the region.
Are there any family house rentals in San Casciano In Val Di Pesa?
In San Casciano In Val Di Pesa, Tuscany, families can choose from a variety of holiday homes, with around 126 options available. This charming town is located in the heart of the Chianti wine region, making it a splendid base for exploring the picturesque countryside. Many of these properties offer spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces where children can enjoy themselves.
Can I rent a holiday home with a pool or hot tub in San Casciano In Val Di Pesa?
In San Casciano In Val Di Pesa, travellers can find a delightful selection of holiday homes with pools and hot tubs, with approximately 155 options available. This picturesque town in Tuscany offers a stunning backdrop of rolling hills and vineyards, great for those seeking a tranquil retreat. Many of these rentals feature private swimming pools, often accompanied by sun loungers and outdoor dining areas, allowing guests to fully enjoy the Tuscan sunshine.
Can I find long-stay holiday rentals in San Casciano In Val Di Pesa?
A long-stay holiday rental in San Casciano In Val Di Pesa 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 San Casciano In Val Di Pesa?
In San Casciano In Val Di Pesa, there are numerous pet-friendly house rentals available, providing a wonderful setting for travellers accompanied by their furry friends. This charming town in Tuscany offers a variety of holiday homes that often feature amenities such as spacious gardens, outdoor terraces, and fully equipped kitchens, making them ideal for families or groups looking to enjoy the picturesque Tuscan countryside.

The area is known for its stunning rolling hills and vineyards, and many rentals are situated near local wineries, allowing guests to indulge in wine tasting while enjoying the scenic views. Additionally, the nearby Chianti region offers beautiful walking trails, great for exploring with pets, and the tranquillity of the countryside makes for a relaxing retreat.
Are there any remote work holiday rentals in San Casciano In Val Di Pesa?
In San Casciano In Val Di Pesa, there are a variety of remote work holiday rentals available, with approximately 173 options to choose from. This picturesque town in Tuscany offers a serene environment, superb for those looking to combine work with leisure. Many of the properties are equipped with essential remote work amenities, including WiFi, dedicated desk spaces, and comfortable office chairs, ensuring a productive atmosphere. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any San Casciano In Val Di Pesa holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in San Casciano In Val Di Pesa 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 San Casciano In Val Di Pesa?
In San Casciano In Val Di Pesa, popular rental amenities include kitchens, refrigerators, and stovetops, making it easy for guests to prepare their own meals. Many properties also feature private pools, providing a refreshing spot to relax during warm days. Additionally, free Wi-Fi is commonly available, ensuring that travellers can stay connected.
When is the best time to visit San Casciano In Val Di Pesa for a holiday rental?
April is the most popular time to visit San Casciano In Val Di Pesa, as the landscape bursts into life with vibrant spring colours, making it ideal for those eager to explore Tuscany's enchanting countryside. This month is particularly pleasant for outdoor activities, with mild temperatures averaging around 15-20°C, great for leisurely strolls through vineyards and olive groves, or visiting local markets where you can sample the region's exquisite culinary offerings.

The peak tourist season runs from July to September, when the warm summer weather draws in crowds eager to experience the charm of this historic town. During these months, you can immerse yourself in the lively atmosphere, attending various festivals and enjoying outdoor dining under the Tuscan sun. However, this bustling season may also mean higher prices for accommodations and activities.

If you're looking for a more budget-friendly option, consider visiting in December, when the town takes on a quieter, more intimate feel. It's cooler, averaging around 5-10°C, the holiday decorations and local festivities can create a magical atmosphere, allowing you to experience San Casciano In Val Di Pesa in a unique light.
How early should I book a San Casciano In Val Di Pesa holiday rental?
Book your San Casciano In Val Di Pesa 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 San Casciano In Val Di Pesa?
In San Casciano In Val Di Pesa, visitors can enjoy a range of attractions that highlight the charm of Tuscany. The historic centre features beautiful medieval architecture and quaint streets, ideal for leisurely strolls. Nearby, the stunning Church of San Giovanni Battista is worth a visit, showcasing remarkable frescoes and an impressive bell tower.

The surrounding countryside is dotted with vineyards and olive groves, making it an excellent area for wine tasting tours, particularly in the renowned Chianti region. For those interested in local history, the ancient ruins of the Etruscan city of Fiesole are just a short drive away, offering insight into the region's rich past.
Can I change or cancel my San Casciano In Val Di Pesa home rental booking on Vrbo?
To find San Casciano In Val Di Pesa 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 San Casciano In Val Di Pesa 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.

More holiday ideas

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