Photo by Ashley Robinson

San Casciano in Val di Pesa holiday lettings

We found 850 holiday rentals — enter your dates for availability

Discover a selection of 22 homes, 13 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.

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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. 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)
  • Circolo Golf Ugolino (5.8 mi / 9.4 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)

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)
  • Torrigiani Garden (7.8 mi / 12.6 km)
  • Giardino degli Iris (8.2 mi / 13.2 km)
  • Florence Botanical Gardens (9.1 mi / 14.6 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 historic centre is an excellent area to stay. This charming neighbourhood boasts a delightful blend of medieval architecture and picturesque landscapes, making it a superb base for exploring the surrounding Tuscan countryside. Here, you can find a variety of properties, ranging from quaint apartments to more spacious villas.

A popular attraction within this area is the stunning Church of San Giovanni Battista, which features beautiful frescoes and offers insight into the local history. Additionally, the nearby Wine Museum is a must-visit for those interested in Tuscany's rich viniculture, showcasing the region's renowned wines and offering tastings.

Moreover, the central location allows easy access to nearby towns and vineyards, giving you the opportunity to immerse yourself in the authentic Tuscan experience.
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 348 available across the region. These apartments are typically situated in charming neighbourhoods and provide a comfortable, home-like atmosphere. Most units are equipped with fully functional kitchens, inviting living areas, and often include balconies or terraces that allow guests to enjoy the stunning Tuscan landscape.

For those seeking more space, there are around 208 holiday houses and 204 villas, which cater well to families or larger groups. These properties usually feature multiple bedrooms, private gardens, and outdoor seating areas, making them ideal for relaxing after a day of exploring the picturesque countryside and nearby wineries.
Are there any family house rentals in San Casciano In Val Di Pesa?
In San Casciano In Val Di Pesa, there are numerous family-friendly house rentals available, with around 129 options to choose from. This charming town in Tuscany is surrounded by picturesque vineyards and olive groves, making it a delightful destination for families. Many of these properties boast spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and families can enjoy al fresco dining.

Visitors will find amenities such as Wi-Fi, air conditioning, and sometimes even private pools, adding to the comfort of their stay. The town's central location allows for easy day trips to nearby attractions like the historic city of Florence and the beautiful Chianti wine region.
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, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 144 options to choose from. This picturesque town in Tuscany is surrounded by stunning countryside and vineyards, making it a delightful destination for those seeking relaxation and natural beauty.

Travellers can expect a variety of amenities in these properties, including private swimming pools, hot tubs, and spacious outdoor areas great for enjoying the warm Tuscan sun. Many rentals also come equipped with fully fitted kitchens, allowing for self-catering, and comfortable living spaces where families or groups can unwind together.

The charming historic centre of San Casciano offers local shops and restaurants, adding to the appeal of staying in the area.
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, offering a fantastic opportunity for travellers wishing to explore Tuscany with their furry companions. Many properties in this picturesque area come equipped with amenities such as spacious gardens, terraces, and fully equipped kitchens, allowing for a comfortable stay.

The charming town is surrounded by beautiful vineyards and olive groves, providing a stunning backdrop for outdoor activities with your pet. Nearby, you'll find the lovely Chianti region, where you can enjoy scenic walks and hikes that are superb for dog owners. Additionally, the area is rich in history and culture, with local attractions such as historic churches and traditional Tuscan architecture, making it an ideal base for exploring the beauty of Tuscany while accommodating your pet.
Are there any remote work holiday rentals in San Casciano In Val Di Pesa?
In San Casciano In Val Di Pesa, there are numerous remote work holiday rentals available, with around 684 options to choose from. This picturesque town in Tuscany is not only steeped in history and surrounded by beautiful vineyards, but it also provides a conducive environment for remote work. Many properties offer free in-room Wi-Fi and additional internet services, ensuring that guests can stay connected while enjoying their tranquil surroundings.

Accommodations range from charming villas to spacious apartments, often featuring comfortable workspaces, lovely gardens, and sometimes even outdoor areas for relaxing breaks. The town itself boasts delightful local shops, restaurants, and stunning views of the Tuscan countryside, making it an ideal setting for those seeking a blend of productivity and leisure. 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 well-equipped kitchens, allowing guests to prepare their own meals and enjoy the local produce. Onsite parking is also commonly available, making it convenient for those travelling by car. Many properties permit pets, suiting travellers who wish to bring their furry companions along. Additionally, a fireplace is a sought-after feature, providing warmth and a cosy atmosphere, particularly during the cooler months. Outdoor spaces, such as gardens, are also prevalent, offering a tranquil setting for relaxation and enjoying the beautiful Tuscan landscape.
When is the best time to visit San Casciano In Val Di Pesa for a holiday rental?
April is a wonderful time to visit San Casciano In Val Di Pesa, as the charming Tuscan countryside comes alive with vibrant blooms and mild temperatures, typically ranging from 10 to 20 degrees Celsius. This month offers a delightful balance of comfortable weather for outdoor activities, including leisurely strolls through vineyards and visits to local markets, all while avoiding the crowds of the high tourist season.

The peak season in this picturesque town runs from July to September, drawing numerous visitors eager to soak in the sun and savour the local cuisine at outdoor trattorias. While this bustling period provides a lively option, it can also mean higher prices and busy attractions. If you prefer a more tranquil experience, visiting in April allows you to enjoy the beauty of the region without the hustle and bustle, making it an ideal time for sightseeing and exploring the rich culture of Tuscany.

For those seeking budget-friendly options, December offers a unique charm with the festive season. Though it is considered low season, the holiday spirit brings a special warmth to the town, providing opportunities for cozy moments and quieter explorations.
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 engage in the charm of Tuscany, characterised by its beautiful landscapes and rich history. The town itself features the impressive Church of San Giovanni Battista, which showcases stunning Renaissance art and architecture. Just a short walk away, the local piazza is a vibrant hub, surrounded by quaint cafes and shops where travellers can sample Tuscan cuisine and wines.

For those interested in vineyards, the surrounding Chianti region is renowned for its wine production, with many wineries offering tours and tastings, allowing visitors to enjoy the scenic countryside. The nearby Castello di Poppiano is another highlight, providing a glimpse into the region's medieval history as well as breathtaking views of the vineyards.

Additionally, San Casciano serves as a convenient base for exploring other great attractions in Tuscany, such as Florence and Siena, both easily accessible for day trips.
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 cabin or a beach house, 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 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.
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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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