- Italy
- Tuscany
- Greve in Chianti
- Pieve di San Leolino
- Rentals by Owner
Discover Your Ideal Pieve di San Leolino, Greve in Chianti, Tuscany Rental by Owner for an Authentic Vacation Experience
Discover Your Perfect Pieve di San Leolino Rentals by Owner
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Pieve di San Leolino Rentals by Owner
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- Pet Friendly
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- Pet Friendly
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- TV
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- Balcony/Terrace
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- Ocean View
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Why Choose Rent By Owner for your Pieve di San Leolino vacation rental?
What makes our Rentals by Owner special?
Popular Areas for Pieve di San Leolino Rentals by Owner
Where are the best neighborhoods to stay in Pieve di San Leolino?
When choosing where to stay in Pieve di San Leolino, Greve in Chianti, Tuscany, you'll find a variety of charming neighborhoods that offer an authentic Tuscan experience. This picturesque region is renowned for its lush vineyards and tranquil countryside, making it the perfect setting for a relaxing getaway. Whether you prefer the peaceful rural areas or the quaint village centers, each neighborhood provides easy access to local charm and stunning landscapes. Booking a vacation rental by owner ensures you enjoy a trustworthy and convenient stay, allowing you to immerse yourself fully in the beauty of Tuscany while enjoying the comfort and reliability that Rent By Owner offers.
Montarioso
In this quiet neighborhood, you can enjoy a peaceful retreat while staying close to the charming sights of Tuscany. It offers a perfect setting for those seeking an authentic experience with convenient access to local attractions.
View 1667+ Rentals in MontariosoIl Serraglio
This area provides a serene ambiance for your stay, allowing you to immerse yourself in the region's natural beauty and tranquil atmosphere. It's ideal for travelers looking for a comfortable rental by owner near the heart of Tuscan countryside.
View 591+ Rentals in Il SerraglioBest Times to Visit Pieve di San Leolino
When should you plan your Rentals by Owner stay?
To make the most of your stay, consider visiting during the region’s optimal seasons when the weather is ideal and local events enhance your experience, allowing you to enjoy the authentic charm of this destination while booking a comfortable rental by owner through Rent By Owner.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, the area comes alive with pleasant weather and lush landscapes, making it ideal for exploring the scenic beauty and local culture. You can enjoy mild daytime temperatures perfect for outdoor activities and sightseeing.
Early Fall (September to October)
As the harvest season begins, the region is vibrant with activity and rich in flavors, attracting visitors seeking authentic Tuscan experiences. The moderate climate offers comfortable days and cooler evenings, enhancing your stay in this picturesque destination.
Off-Season Highlights
Winter (December to February)
During these months, the area tends to be quieter, providing a peaceful retreat for travelers seeking solitude or low-key exploration. While the weather can be chilly, cozy accommodations offer a warm escape in this charming region.
Early Spring (March to April)
Before the peak of tourist season, the countryside begins to bloom, yet crowds are scarce, giving you a relaxed experience. Expect variable weather and cooler temperatures suitable for leisurely visits and planning your adventures.
Weekly Weather Forecast for Pieve di San Leolino
How to Book Your Pieve di San Leolino vacation rental
What's our booking process?
Booking Steps
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Explore and book the perfect rental in Pieve di San Leolino
Common Rentals by Owner Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or terrace perfect for relaxing and dining al fresco amid the scenic surroundings.
- Make use of a well-maintained swimming pool that offers a refreshing escape in the warm Tuscan climate.
- Take advantage of extensive garden spaces ideal for leisurely strolls or outdoor activities with family and friends.
- Benefit from outdoor grilling facilities to prepare authentic Tuscan meals while soaking in the picturesque views.
- Experience the tranquility of a private courtyard or gazebo, providing a peaceful setting during your stay here.
- Utilize designated parking areas within the outdoor space for convenience and security during your visit.
- Enjoy access to scenic outdoor seating areas designed for catching sunsets or enjoying quiet mornings in the region.
Top Attractions Around Pieve di San Leolino
What attractions are nearby?
Within this charming region, you can explore scenic wine tastings, indulge in authentic Tuscan cuisine, or enjoy peaceful walks through picturesque countryside, all just moments from your Rent By Owner rental in Pieve di San Leolino, Greve in Chianti.

Family Activities
- Visit the Greve in Chianti Wine Museum: Discover the region's rich winemaking heritage through interactive exhibits that captivate both children and adults alike.
- Explore the local countryside on family-friendly hiking trails: Embark on scenic walks through the rolling Tuscan hills, perfect for soaking in the area's natural beauty with your loved ones.
- Participate in a traditional olive oil tasting experience: Engage in authentic tastings at nearby farms, offering an educational and delicious activity for families in this charming part of Tuscany.
- Enjoy a family picnic in the local vineyards: Relax amidst the picturesque landscapes while savoring Tuscan delicacies, making for a memorable day in the heart of the region.
Adult Activities
- Wine Tasting Tours: You can explore renowned local wineries to sample exceptional Chianti wines amidst scenic vineyard landscapes.
- Cooking Classes: Participate in authentic Tuscan cooking experiences where you learn to prepare regional dishes using fresh, local ingredients.
- Historical Village Walks: Discover the charming streets and historical sites of the area on guided walks that highlight its rich cultural heritage.
- Nature Excursions: Enjoy tranquil hikes or cycling routes through the rolling hills and lush countryside surrounding this destination for a relaxing outdoor experience.
Pieve di San Leolino Travel Tips
How Can You Make the Most of Your Stay?
- Explore local wineries: Take time to visit the nearby vineyards to fully appreciate the region's renowned wine culture, which enriches your stay in this picturesque destination.
- Opt for a rental with a view: Choosing a vacation home that offers scenic vistas of the rolling hills enhances your experience and allows you to enjoy the area's natural beauty from the comfort of your accommodation.
- Book activities in advance: Secure guided tours or private tastings early to ensure you make the most of your time here without missing out on popular experiences in the region.
- Discover authentic local cuisine: Dine at locally loved eateries or prepare traditional dishes in your rental to immerse yourself in the culinary culture that the area proudly offers.
Transportation Options
- Car Rentals: You can rent a vehicle locally to explore the scenic countryside and charming towns surrounding this part of Tuscany at your own pace.
- Bus Services: Regular regional bus routes connect here with nearby cities, offering an affordable and convenient way to travel without a car.
- Private Transfers: Private transfer services are available for door-to-door comfort, ideal for those seeking a stress-free journey into the heart of Tuscany.
- Taxi Services: Taxis operate in the area, providing flexible transportation options to visit local attractions or reach nearby towns easily.
Local Customs Options
- Respect for Local Religious Traditions: You should be mindful of the area's religious sites and customs, especially during local festivals and church services, demonstrating your appreciation for this destination’s spiritual heritage.
- Greeting Etiquette: It’s customary to greet locals with a friendly handshake or a warm "buongiorno," reflecting the region’s welcoming and personable atmosphere.
- Appreciation for Regional Cuisine: When dining or purchasing local products, expressing genuine interest and gratitude for Tuscan flavors shows respect for this destination’s culinary traditions.
- Environmental Respect: You are encouraged to follow sustainable practices by conserving water and minimizing waste, supporting the region’s commitment to preserving its natural beauty and scenic landscapes.
Frequently Asked Questions About Pieve di San Leolino Rentals by Owner
1. What are the top vacation rentals in Pieve di San Leolino?
There are a lot of options in Pieve di San Leolino. If you plan on staying in the Pieve di San Leolino area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pieve di San Leolino:
- Terre di Baccio
- Quiet and Beautiful Property, Large Pool, Airco in bedrooms
- Villa in Lucarelli with 6 bedrooms sleeps 10
- Luxury Historic Villa San Piero, Panoramic Views, Romantic Chapel, Wine Cellar
- "TERRACE BELL"
- Tuscany Stone Villa With Spectacular View
- Typical Tuscan farmhouse in charming position between Panzano -Greve in Chianti
- La Misura cottage with swimming pool
- Luxury Chianti Nest lost in the middle of Wineries
- Casa Grazia, quiet nest near the center. free parking all over the street.
2. How many Rentbyowner vacation rentals are available in Pieve di San Leolino?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 427 in the Pieve di San Leolino area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Pieve di San Leolino.
3. What is the cancellation policy for a rental by owner in this area?
4. How do I confirm the availability of a property in this region?
5. Are there any additional fees I should be aware of when booking directly with an owner?
6. What amenities are typically included in rentals by owner here?
7. Is it safe to book a rental directly with an owner in this destination?
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