Discover Your Perfect Montegrossi Rentals by Owner

Montegrossi Rentals by Owner

10.0 (11 Reviews)
House
L' Eroico
  • Air Conditioner
  • TV
  • Balcony/Terrace
View Availability
More Top-Rated Rentals by Owner in Montegrossi Area

Why Choose Rent By Owner for your Montegrossi vacation rental?

What makes our Rentals by Owner special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Montegrossi

When should you plan your Rentals by Owner stay?

Choosing the ideal time to vacation here ensures you experience the region’s authentic charm and enjoy your rental by owner in Montegrossi, Gaiole in Chianti with optimal weather and fewer crowds throughout the year.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, you can enjoy the region's lush landscapes and vibrant local events, making it an ideal time for exploring without the peak summer crowds.

Average Temperature Daytime: around 25°C - Nighttime: about 14°C
autumn
Early Fall (September to October)

This season offers mild weather and fewer tourists, providing a perfect backdrop for discovering the area's scenic beauty and authentic atmosphere.

Average Temperature Daytime: approximately 24°C - Nighttime: roughly 13°C

Off-Season Highlights

image
Winter (December to February)

During the colder months, the tranquility of this destination allows for a peaceful retreat away from the busy tourist season, with many accommodations offering cozy stays.

Average Temperature Daytime: around 10°C - Nighttime: close to 3°C
image
Early Spring (March to April)

As the region awakens from winter, the early spring months provide a quiet and serene setting, perfect for travelers seeking a more intimate experience in this part of Tuscany.

Average Temperature Daytime: about 15°C - Nighttime: around 5°C

Weekly Weather Forecast for Montegrossi

How to Book Your Montegrossi vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Montegrossi

More Top-Rated Rentals by Owner in Montegrossi Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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 inviting outdoor dining areas perfect for savoring Tuscan cuisine under the region's warm sunshine.
  • Relax by a private swimming pool that offers stunning views of the rolling Chianti hills.
  • Benefit from well-maintained garden spaces ideal for leisurely walks or picnics amidst local flora.
  • Take advantage of spacious terraces or patios designed to maximize the scenic beauty of your surroundings.
  • Discover outdoor lounge areas where you can unwind and soak in the tranquility of this picturesque area.
  • Utilize barbecue facilities to prepare authentic Italian grilled dishes during your stay here.
  • Explore expansive outdoor spaces suitable for activities like yoga, meditation, or simply enjoying the fresh air.

Top Attractions Around Montegrossi

What attractions are nearby?

Here, you can enjoy exploring scenic vineyards, indulging in authentic Tuscan cuisine, or taking leisurely walks through picturesque countryside—all conveniently close to your rental by owner in this charming region.

image
image

Family Activities

  • Wine and Olive Oil Tasting Tours: Explore local vineyards and olive groves to learn about traditional production methods right in the heart of this region’s renowned countryside.
  • Family-Friendly Cooking Classes: Participate in hands-on culinary experiences designed for families, where you can create authentic Tuscan dishes together.
  • Guided Nature Walks and Hiking: Discover scenic trails suitable for all ages, offering breathtaking views of the rolling hills and picturesque landscapes of the area.
  • Visiting Local Castles and Historic Sites: Step back in time by exploring well-preserved castles and historical landmarks that provide engaging stories for both kids and adults.
image

Adult Activities

  • Wine Tasting Tours: You can explore the renowned vineyards of the Chianti region, experiencing its world-famous wines right at their source.
  • Cooking Classes: Participate in authentic Tuscan cooking classes that offer an immersive taste of local cuisine and culinary traditions.
  • Historical Church Visits: Discover the area's rich history by visiting centuries-old churches and religious sites dotted around here.
  • Guided Nature Walks: Enjoy scenic walks through the rolling hills and lush landscapes, perfect for unwinding and absorbing the region's natural beauty.

Montegrossi Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local wineries: Take advantage of the region’s renowned wine heritage by booking a private tour to sample authentic Chianti wines directly from nearby vineyards.
  • Visit charming villages: Spend time wandering through nearby villages and experiencing the rustic charm and traditional Tuscan architecture that define this area.
  • Savor regional cuisine: Indulge in authentic Tuscan dishes at local trattorias—or better yet, enjoy home-cooked meals if your rental offers a kitchen for fresh, regional ingredients.
  • Plan outdoor adventures: Make the most of the scenic landscape with activities like hiking or cycling along the region’s picturesque countryside paths, immersing yourself in the tranquil surroundings.

Transportation Options

  • Rental Cars: Opting for a rental car offers you the flexibility to explore the scenic countryside and charming villages at your own pace, just steps from your vacation home here.
  • Local Taxis and Private Transfers: For convenience and comfort, local taxi services and private transfer options provide door-to-door service throughout the region, making your travels hassle-free.
  • Bus Services: Regional bus routes connect this destination to nearby towns and cities, providing an affordable and reliable transportation option during your stay.
  • Train Stations: The closest train stations offer easy connections to major Italian cities, allowing you to plan day trips or longer excursions with ease from your base here.

Local Customs Options

  • Greetings and Social Etiquette: When visiting here, it is customary to greet locals with a polite handshake or a friendly nod, reflecting the warm hospitality typical of this region in Tuscany.
  • Dining Customs: Meals often involve shared dishes, and expressing appreciation through simple phrases like "Buon Appetito" enhances your experience while respecting local dining traditions.
  • Respect for Religious Sites: Visitors should dress modestly and behave respectfully when entering churches and other religious sites throughout the area, honoring longstanding customs in this part of Italy.
  • Wine and Food Appreciation: Tasting local wines and regional specialties should be done with mindfulness, as these customs are deeply rooted in the cultural identity of this destination in Tuscany.

Frequently Asked Questions About Montegrossi Rentals by Owner

1. What are the top vacation rentals in Montegrossi?

There are a lot of options in Montegrossi. If you plan on staying in the Montegrossi area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Montegrossi:

2. How many Rentbyowner vacation rentals are available in Montegrossi?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 326 in the Montegrossi 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 Montegrossi. 

3. What is the cancellation policy for a rental by owner in this region?

The cancellation policy varies by property, so it's important to review the specific listing details or contact the owner directly for information regarding cancellation terms and any applicable fees.

4. How do I confirm the availability of a rental owned by an individual here?

Availability updates are provided on the listing page, but confirming directly with the owner can ensure the most accurate and up-to-date information before completing your booking.

5. Are there any additional fees or security deposits required for booking a rental by owner?

Additional fees or security deposits are specified in the listing details. It's recommended to read these carefully or inquire directly with the owner to understand all costs involved.

6. What amenities and features can I expect from an owner-operated rental in this area?

Amenities vary between properties, so it’s best to review each listing for detailed information about what’s included, and contact the owner if you have specific requirements.

7. How can I contact the owner for special requests or questions about my stay?

You can communicate directly with the owner through the messaging platform provided on the booking site, allowing you to ask questions or make special arrangements prior to your arrival.

More Rentals You May Like Near Montegrossi

More Top-Rated Rentals by Owner in Montegrossi Area