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San Casciano in Val di Pesa vacation rentals

We found 805 vacation rentals — enter your dates for availability

Discover a selection of 22 homes, 13 apartments, and other vacation rentals in San Casciano in Val di Pesa that are perfect for your trip. Vacation homes provide the amenities you need and want for your stay with friends, family, or just your pet, such as WiFi and a fireplace. At the end of the day, you'll be able to choose a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Find out more about San Casciano in Val di Pesa

Why visit San Casciano in Val di Pesa

  • Charming Piazzas: Explore picturesque squares that embody the romantic essence of Tuscany.
  • Historic Churches: Visit beautiful churches that showcase the rich cultural heritage of the region.
  • Wine Tastings: Indulge in the local Chianti wine culture with delightful tastings at nearby vineyards.
  • Stunning Villas: Tour exquisite Italian villas that highlight the elegance of Tuscan architecture.
  • Breathtaking Countryside: Experience the serene beauty of the Chianti Hills with scenic outdoor adventures.

Popular types of accommodation in San Casciano in Val di Pesa

If you're looking for the perfect getaway in San Casciano in Val di Pesa, we’ve got you covered with a variety of charming accommodation options. Our most popular types include spacious apartments, exquisite villas, and houses. Whether you're seeking a villa holiday with multiple bedrooms or a cozy retreat, you'll find the ideal holiday villas to make your stay memorable. Experience the beauty of Tuscany with comfort and style.

  • Apartments: The top choice for visitors in San Casciano in Val di Pesa, offering convenience and comfort for couples or solo travelers.
  • Villas: A favored option for those seeking luxury and spaciousness, perfect for family gatherings or special occasions.
  • Houses: Ideal for groups or families wanting a homey atmosphere with all the amenities.
  • Caravan Parks: A unique and budget-friendly option for adventurous travelers wanting a taste of outdoor living.
  • Cottages: A delightful choice for a quaint and cozy retreat in the Tuscan countryside.**

Top attractions in and around San Casciano in Val di Pesa

San Casciano in Val di Pesa is perfect for romantic getaways and outdoor adventures. Visitors can explore charming piazzas, historic churches, and elegant palaces while enjoying the rich culture of Tuscany. Don't miss the opportunity to tour stunning Italian villas, indulge in wine tastings, and experience the breathtaking Chianti Hills. This destination offers a delightful blend of romance, entertainment, and cultural exploration for every traveler.

  • Monastery of Sorelle Clarisse: Nestled in San Casciano in Val di Pesa, this serene monastery offers a glimpse into monastic life with its tranquil atmosphere and rich cultural heritage.
  • Ponte Vecchio: An iconic historic bridge located 8 miles away, renowned for its picturesque views and unique shops, making it a perfect spot for photos and souvenirs.
  • Uffizi Gallery: Also 8 miles away, this renowned art museum houses masterpieces from the Renaissance, providing an immersive experience into Italy's artistic legacy.

Things to do recommended for couples

San Casciano in Val di Pesa offers a romantic getaway with wine tasting in local vineyards, leisurely walks through charming medieval streets, and intimate dinners at cozy trattorias. Don't miss a sunset view over the rolling hills—it's the perfect backdrop for a memorable couple's experience.

Things to do recommended for families

Your family will delight in exploring the charming streets of San Casciano in Val di Pesa, where kids can enjoy local gelato shops. Visit nearby vineyards for family-friendly tours, and don’t miss the chance to hike scenic trails that offer stunning views of the Tuscan countryside.

Things to do recommended for groups

Groups visiting San Casciano in Val di Pesa can enjoy a wine tasting tour at local vineyards, participate in a traditional Tuscan cooking class, and explore the charming medieval town with its picturesque streets and stunning views of the Chianti countryside.

*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 San Casciano in Val di Pesa

If you're planning a trip with a group, family, or pets, or if you're interested in longer stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to San Casciano in Val di Pesa with a group: Think about how many bedrooms you'll require and any additional features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to San Casciano in Val di Pesa with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with finding age-appropriate 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 San Casciano in Val di Pesa: For many families, a vacation wouldn’t feel complete without their furry companion. If you relate to this, explore Vrbo listings that welcome pets. Most pet-friendly properties offer feeding bowls and beds to ensure that every family member feels comfortable and at home.
  • Planning for a long term stay visiting San Casciano in Val di Pesa: If you're seeking vacation rentals with special offers for month-long stays, 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 amenities like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around San Casciano in Val di Pesa

San Casciano in Val di Pesa offers an unforgettable Tuscan getaway, perfect for romance and relaxation. Explore the charming countryside views and indulge in the local wine culture of Chianti. Families will find plenty to enjoy in this tranquil setting, surrounded by friendly locals and rich history. Whether you're wandering through picturesque villages or savoring gourmet meals, San Casciano promises a delightful blend of serenity and entertainment in the heart of Tuscany.

  • Florence: Florence, located 8 miles from San Casciano in Val di Pesa, is a cultural gem that draws travelers seeking rich history and vibrant city life. Known as the birthplace of the Renaissance, it offers an array of attractions including the iconic piazza squares and historic landmarks. Visitors can enjoy a variety of activities such as shopping in chic boutiques, indulging in spa treatments, or taking in a performance at one of its elegant theaters. Florence’s artistic heritage, exemplified by renowned museums and galleries, makes it an essential stop for any traveler.
  • Mercatale Val di Pesa: Nestled within the San Casciano in Val di Pesa area, Mercatale Val di Pesa is a charming village perfect for those seeking a romantic and outdoor experience. While it may not be known for beaches, its natural beauty and tranquil surroundings provide a lovely escape. Visitors can explore local resorts and unwind in spas, or even take advantage of nearby ski lifts during winter months. The village is rich in history, with notable landmarks that invite exploration and discovery.
  • Sant'Andrea in Percussina: This picturesque village, also located near San Casciano in Val di Pesa, is ideal for adventurous travelers looking for outdoor activities. Sant'Andrea in Percussina offers opportunities for swimming and enjoying the scenic beauty of its landscapes. Highlights include a modern tower that provides stunning views and an event conference venue that attracts visitors. The village's inviting atmosphere is perfect for couples seeking a romantic getaway or anyone looking to connect with nature.

Best time to go to San Casciano in Val di Pesa

If you're planning a trip to San Casciano in Val di Pesa, it's a good idea to check both the weather and property rates. The warmest months are July and August. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January41.4°F (5.2°C)Light RainMostly SunnyAverageSlightly Low
February43.0°F (6.1°C)Light RainMostly SunnyAverageSlightly Low
March47.8°F (8.8°C)Light RainMostly SunnyAverageAverage
April54.3°F (12.4°C)Light RainMostly SunnySlightly HighAverage
May60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
June69.6°F (20.9°C)Light RainSunnyAverageSlightly High
July75.2°F (24.0°C)No Rain (Dry)SunnySlightly HighSlightly High
August75.2°F (24.0°C)No Rain (Dry)SunnyAverageSlightly High
September67.3°F (19.6°C)Light RainMostly SunnySlightly HighAverage
October58.8°F (14.9°C)Light RainMostly SunnySlightly LowAverage
November50.2°F (10.1°C)Light RainMostly SunnySlightly LowSlightly Low
December43.5°F (6.4°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers an easy-to-use platform where you can plan new trips, resume your previous work, or organize your travel arrangements. You’ll find your saved or booked properties neatly organized under categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Tranquil 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 coffeehouses, this relaxing city won't disappoint. Piazza di Santa Maria Novella and Cathedral of Santa Maria del Fiore are just a couple of the must-sees in the area. If you need more space to accommodate a family vacation or friends trip, 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 find attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes San Casciano in Val di Pesa a fun spot to vacation. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 exciting outdoor activities or just want to spend some time taking in the scenery, San Casciano in Val di Pesa is a great place to get outside. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Florence Botanical Gardens (9.1 mi / 14.6 km)
  • Villa di Castello (11.3 mi / 18.2 km)

Traveling to and around San Casciano in Val di Pesa

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

Frequently asked questions

What is the best area to stay in San Casciano In Val Di Pesa, Tuscany, Italy when booking a vacation rental?
When considering a vacation rental in San Casciano In Val Di Pesa, a popular area to stay is the historic center. This charming neighborhood is characterized by its picturesque streets and stunning medieval architecture, providing a truly authentic Tuscan experience. Visitors can easily explore attractions such as the beautiful Church of San Giovanni Battista and the scenic Piazza della Repubblica, where local markets and events often take place.

Another appealing option is the surrounding countryside, which offers a serene atmosphere and breathtaking views of the rolling hills and vineyards that Tuscany is famous for. This area is superb for those looking to unwind in a tranquil setting while still being a short drive from the vibrant local culture. Additionally, there are numerous vineyards and wineries nearby, providing excellent opportunities for wine tasting and tours.

Overall, San Casciano In Val Di Pesa features a variety of properties, ranging from cozy apartments in the heart of town to charming villas located in the countryside.
How much does it cost to rent a vacation home in San Casciano In Val Di Pesa?
Prices for vacation 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 vacation 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 vacation rental accomodation in San Casciano In Val Di Pesa?
In San Casciano In Val Di Pesa, apartments are the most popular vacation rental option, with about 87 available in the area. These apartments are often situated in charming neighborhoods, providing easy access to local shops, restaurants, and the beautiful Tuscan countryside. Most units come equipped with fully functional kitchens, cozy living areas, and balconies where guests can enjoy stunning views of the rolling hills.

For those looking for more spacious rooms, there are approximately 52 vacation houses and 51 villas available, which are ideal for families or larger groups. These properties typically feature multiple bedrooms, expansive living spaces, private gardens, and outdoor areas superb for enjoying al fresco dining under the Tuscan sun. Additionally, several cottages can be found, offering a quaint and rustic experience while still being close to the region's attractions.
Are there any family house rentals in San Casciano In Val Di Pesa?
In San Casciano In Val Di Pesa, Tuscany, there is a substantial selection of family-friendly houses, with around 129 options available for visitors. This charming area is known for its picturesque landscapes and proximity to popular attractions such as the beautiful vineyards of Chianti and the historic city of Florence, which is just a short drive away.

Many of these homes come equipped with spacious living areas, full kitchens for preparing family meals, and outdoor spaces where children can run and play. Additional amenities often include Wi-Fi, air conditioning, and sometimes even private pools or gardens for relaxation. The local environment encourages exploration, with opportunities for hiking and enjoying the breathtaking Tuscan countryside.

Families can take advantage of the nearby cultural experiences, such as visiting local markets or enjoying traditional Tuscan cuisine in nearby villages.
Can I rent a vacation home with a pool or hot tub in San Casciano In Val Di Pesa?
In San Casciano In Val Di Pesa, travelers can find a variety of vacation homes available for rent with pools or hot tubs, totaling around 144 options. This charming town in Tuscany is surrounded by picturesque vineyards and rolling hills, making it a serene getaway. Many of the properties come equipped with private pools, hot tubs, and spacious outdoor areas ideal for soaking up the sun and enjoying the stunning countryside views.

Amenities often include fully equipped kitchens, allowing guests to prepare meals with local ingredients, as well as comfortable living spaces for relaxation after a day of exploring. Some rentals may also offer additional features like barbecue facilities and beautiful gardens, great for outdoor dining.
Can I find long-stay vacation rentals in San Casciano In Val Di Pesa?
A long-stay vacation 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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in San Casciano In Val Di Pesa?
Yes, there are numerous pet-friendly house rentals available in San Casciano In Val Di Pesa, with over 100 options to choose from. This picturesque town in Tuscany offers vacation homes that often feature rustic charm and modern comforts, including fully equipped kitchens, spacious living areas, and outdoor spaces like gardens or terraces. Many properties also provide amenities such as Wi-Fi, air conditioning, and private parking, making them ideal for travelers with pets and families.

San Casciano In Val Di Pesa is surrounded by beautiful Tuscan countryside, providing ample opportunities for pet-friendly outdoor activities. The area is dotted with vineyards and olive groves, where guests can enjoy leisurely strolls with their pets while taking in the stunning landscape. Additionally, nearby parks and walking trails offer great spots for exercise and exploration, ensuring both pets and their owners have a delightful stay in this charming region.
Are there any remote work vacation rentals in San Casciano In Val Di Pesa?
In San Casciano In Val Di Pesa, there are numerous vacation rentals that cater to remote work needs, with around 171 options available throughout the area. This picturesque town in Tuscany offers a serene environment, great for working remotely while surrounded by stunning landscapes. Many properties come equipped with high-speed internet and Wi-Fi, allowing for a seamless work experience.

Travelers can expect accommodations ranging from charming villas to cozy apartments, often featuring dedicated workspaces and comfortable living areas. Additionally, some rentals provide amenities such as outdoor terraces or gardens where you can take breaks and enjoy the beautiful Tuscan scenery.

The town itself is rich in history and culture, with local wineries and olive groves nearby, providing opportunities for relaxation after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any San Casciano In Val Di Pesa vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in San Casciano In Val Di Pesa with parking available—perfect for families or travelers 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, allowing guests to prepare their own meals with local ingredients from the nearby markets. Onsite parking is commonly available, providing convenience for those traveling by car. Many properties are pet-friendly, welcoming furry companions to join the stay. Travelers can also enjoy the warmth and ambiance of fireplaces, great for cozy evenings after exploring the beautiful Tuscan countryside. Additionally, gardens are a frequent feature, offering serene outdoor spaces to relax and take in the picturesque surroundings.
When is the best time to visit San Casciano In Val Di Pesa for a vacation rental?
April is the most popular month to visit San Casciano In Val Di Pesa, as it marks the beginning of spring in Tuscany, bringing mild weather and vibrant landscapes. During this time, visitors can enjoy comfortable temperatures ranging from the low 50s to the mid-70s Fahrenheit, making it ideal for outdoor activities such as vineyard tours, scenic walks, and exploring the charming town's historic sites.

The peak season, running from July to September, draws a lively crowd eager to experience the warmth of summer in Tuscany. This bustling period is filled with outdoor dining, wine festivals, and various cultural events, creating an energetic atmosphere that appeals to many travelers. However, if you prefer a more relaxed experience with fewer tourists, visiting in April ensures you can fully appreciate the beauty of the Tuscan countryside without the summer crowds.

For those looking for more budget-friendly options, December offers a unique charm with fewer visitors and the opportunity to experience local holiday traditions. The weather is cooler, generally ranging from the low 30s to the mid-50s Fahrenheit, but the picturesque landscapes dusted with light frost can provide a cozy backdrop for a winter getaway.
How early should I book a San Casciano In Val Di Pesa vacation rental?
Book your San Casciano In Val Di Pesa 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 San Casciano In Val Di Pesa, Tuscany, Italy?
In San Casciano In Val Di Pesa, visitors can immerse themselves in the charm of Tuscany with its picturesque landscapes and rich history. The town itself boasts the stunning Church of Santa Maria del Prato, known for its beautiful frescoes and serene ambiance. Just a short drive away, travelers can explore the vineyards and olive groves that dot the Chianti region, offering wine tastings and tours that highlight the area's renowned wines.

The nearby Castello di Bibbione is also a must-see, providing a glimpse into the region's medieval past, along with breathtaking views of the rolling hills. For those seeking outdoor activities, the surrounding countryside presents numerous hiking and biking trails that allow for exploration of the stunning Tuscan landscape.
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 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 San Casciano In Val Di Pesa 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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