San Casciano in Val di Pesa vacation rentals

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Immerse yourself in the enchanting charm of San Casciano in Val di Pesa, where picturesque piazzas and historic churches weave a tapestry of Tuscany's rich heritage. Explore the breathtaking Chianti Hills, indulge in wine tastings at local vineyards, and wander through exquisite villas that showcase elegant Italian architecture. Ideal for groups and families, our selection of spacious apartments and luxurious villas offers the perfect blend of comfort and convenience, ensuring a memorable home-like retreat amidst this stunning landscape.

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

Showing deals for:Dec 4 - Dec 11

apt Androne
Exterior
Pool
Terrace/patio
Exceptional
(40 reviews)

Large estate with private pool comprising 7 apartments - up to 24 people

Greve in Chianti

27% off
$828
$5,798 for 7 nights
All fees included
Large estate with private pool comprising 7 apartments - up to 24 people
Property grounds
Interior
Room
Dining
Exceptional
(64 reviews)

Locanda del podestà: 17th century mansion in Chianti

Montespertoli

8% off
$237
$1,661 for 7 nights
All fees included
Locanda del podestà: 17th century mansion in Chianti
Private kitchen
Pool
Exterior
Property grounds
Exceptional
(28 reviews)

RELAX BETWEEN OLIVES AND WINEYARDS IN THE CHIANTI, ONLY 35MINUTES FROM FLORENCE!

San Casciano in Val di Pesa

8% off
$152
$1,065 for 7 nights
All fees included
RELAX BETWEEN OLIVES AND WINEYARDS IN THE CHIANTI, ONLY 35MINUTES FROM FLORENCE!
Interior
Exterior detail
Exterior
Living area
Exceptional
(51 reviews)

Florentine Hills LE SCALETTE

Scandicci

8% off
$368
$2,579 for 7 nights
All fees included
Florentine Hills LE SCALETTE
Outdoor dining
Outdoor dining
Property grounds
Dining
Exceptional
(112 reviews)

Exclusive Estate | Personal Concierge & Heated Pool

Impruneta

9% off
$1,735
$12,146 for 7 nights
All fees included
Exclusive Estate | Personal Concierge & Heated Pool
Exterior
Pool
Property grounds
Dining
Exceptional
(9 reviews)

RELAX BETWEEN OLIVES AND WINEYARDS, NEAR FLORENCE

San Casciano in Val di Pesa

7% off
$170
$1,188 for 7 nights
All fees included
RELAX BETWEEN OLIVES AND WINEYARDS, NEAR FLORENCE
Living area
Property grounds
Living area
Exterior
Exceptional
(5 reviews)

7km Florence, garden, terrace & relax!

San Casciano in Val di Pesa

9% off
$87
$606 for 7 nights
All fees included
7km Florence, garden, terrace & relax!
Property grounds
Terrace/patio
Interior
Living area
Exceptional
(5 reviews)

Le Piccole Scalette"Under the Tuscan Sun"

Scandicci

8% off
$293
$2,050 for 7 nights
All fees included
Le Piccole Scalette"Under the Tuscan Sun"

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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)
  • 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 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)
  • Olmo (14.5 mi / 23.4 km)
  • Alta Val d'Elsa River Park (18.8 mi / 30.3 km)
  • Florence Botanical Gardens (9.1 mi / 14.6 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 are the best areas to stay in a vacation rental in San Casciano in Val di Pesa?
Vacation rentals in San Casciano in Val di Pesa offer a variety of settings, and while the town itself is charming, specific areas provide distinct experiences. The best area depends on what kind of stay you're looking for, with options for those who enjoy local amenities and those seeking a more secluded retreat.
  • Il Serraglio: Ideal for couples or small groups who enjoy being close to local life, this area features a selection of houses and villas. You'll find properties with kitchens, parking, and pools, and it boasts numerous restaurants, cafes, and bars for easy dining and entertainment.
For families or larger groups seeking more space and privacy, the wider San Casciano in Val di Pesa area offers many more options, particularly villas and larger homes with ample room to settle in comfortably.
What are the most popular vacation rentals in San Casciano in Val di Pesa?
Vacation rentals in San Casciano in Val di Pesa are most popular for their variety of property types, offering space and privacy for different guest needs. Apartments are widely available, with over 80 options, providing a convenient base for exploring the region. Houses are also a top choice, with nearly 70 properties, often preferred by families or groups seeking more room to spread out. Villas, with over 50 available, are highly sought after for their classic Tuscan experience, offering luxurious amenities and scenic settings. These property types are spread throughout the area, allowing guests to find a whole place to themselves, whether they prefer a lively town setting or a more secluded countryside retreat.
What amenities do vacation rentals in San Casciano in Val di Pesa usually offer?
Vacation rentals in San Casciano in Val di Pesa typically offer a range of amenities designed for a comfortable and convenient stay. You'll often find fully equipped kitchens, perfect for preparing meals with local ingredients, along with fast Wi-Fi and laundry facilities for longer stays. Many properties also provide ample parking, which is helpful for exploring the Tuscan countryside. Outdoor areas are common, allowing guests to enjoy the beautiful surroundings, and a significant number of rentals feature pools for relaxation. Pet-friendly options are also widely available, ensuring your furry companions can join your trip.
Are there family-friendly vacation rentals in San Casciano in Val di Pesa?
Yes, San Casciano in Val di Pesa offers over 140 family-friendly vacation rentals, providing comfortable and spacious options for your trip. You'll find a wide selection of apartments, houses, and villas, many of which are designed to accommodate families of all sizes. These properties often come equipped with full kitchens, dishwashers, and microwaves, making meal preparation easy. Many also include amenities like high chairs and travel cribs, along with outdoor play areas or games, ensuring a convenient stay for those traveling with children. While family-friendly options are available throughout the region, you can find several properties in areas like Il Serraglio, which offers a mix of private homes and villas.
Are there pet-friendly vacation rentals in San Casciano in Val di Pesa?
Yes, you'll find over 140 pet-friendly vacation rentals in San Casciano in Val di Pesa, making it easy to bring your furry companions along. These options include numerous apartments, houses, and villas, offering plenty of space for both you and your pets. Many properties feature amenities such as secured yards, providing a safe outdoor space for pets to enjoy. While pet-friendly rentals are available across the area, you can find a selection of properties in Il Serraglio, which offers a mix of apartments and private homes.
What are the best areas for group vacation rentals in San Casciano in Val di Pesa?
For groups traveling to San Casciano in Val di Pesa, the area offers nearly 100 vacation rentals with ample space and amenities. You'll find many houses and villas, which are ideal for larger gatherings, providing multiple bedrooms, spacious living areas, and privacy. These properties often include fully equipped kitchens for shared meals, outdoor areas for socializing, and plenty of parking for multiple vehicles. While group-friendly options are available throughout the region, a selection of properties suitable for groups can be found in areas like Il Serraglio, featuring both private homes and villas.
What are the best luxury vacation rentals in San Casciano in Val di Pesa?
San Casciano in Val di Pesa offers over 60 luxury vacation rentals, providing an elevated experience for guests. Villas are a prominent choice for luxury stays, with many offering private pools, stunning views, and spacious outdoor areas. You'll also find upscale houses that feature amenities like hot tubs, fireplaces, and elegant furnishings. These premium properties are available across the region, with a selection of luxury villas and private homes also found in areas such as Il Serraglio.
Are there any budget-friendly vacation rentals in San Casciano in Val di Pesa?
Yes, San Casciano in Val di Pesa offers over 110 budget-friendly vacation rentals, providing great value for your stay. Apartments and houses are common choices for guests seeking affordability, often providing more space and amenities than traditional hotel rooms. Many of these properties include fully equipped kitchens, allowing you to save on dining out, along with free Wi-Fi and parking. Choosing a whole home means groups can split costs, and you can find a selection of budget-friendly options in areas like Il Serraglio, which offers a mix of apartments and private homes.
Are there any vacation rentals in San Casciano in Val di Pesa with a pool?
Yes, you'll find over 170 vacation rentals in San Casciano in Val di Pesa that feature pools, perfect for relaxing under the Tuscan sun. Many of these properties offer private pools for enhanced privacy, while others provide shared pools, often with spacious outdoor areas for lounging. You can choose from apartments, houses, and villas, with outdoor pools being a common feature across these property types. A selection of properties with pools can be found in areas like Il Serraglio, which offers a mix of private homes and villas.
Are there any vacation rentals in San Casciano in Val di Pesa with a hot tub?
Yes, San Casciano in Val di Pesa offers around 30 vacation rentals equipped with a hot tub, providing a relaxing amenity for your stay. These properties include houses and villas, often featuring outdoor hot tubs where you can unwind after a day of exploring. You'll find a selection of properties with hot tubs in areas like Il Serraglio, which offers a mix of private homes and villas.
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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