1. Italy
  2. Tuscany
  3. Roccastrada
  4. Montemassi
  5. Rentals by Owner

Discover Your Perfect Montemassi Rentals by Owner

Montemassi Rentals by Owner

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10.0 (2 Reviews)
Apartment
Tenuta Poggio Piero
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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10.0 (2 Reviews)
House
Sequerciani
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Montemassi Area

Why Choose Rent By Owner for your Montemassi vacation rental?

What makes our Rentals by Owner special?

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

Best Times to Visit Montemassi

When should you plan your Rentals by Owner stay?

Choosing the ideal time to vacation here ensures you enjoy the region’s authentic charm and temperate climate, making your booking through Rent By Owner both convenient and stress-free for a memorable stay in this beautiful part of Tuscany.

Peak Season Highlights

spring
May to September

During these months, you can enjoy warm weather and longer daylight hours, ideal for exploring the scenic countryside and vineyards.

Average Temperature Daytime: 25°C to 30°C - Nighttime: 15°C to 20°C
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April and October

These shoulder months offer pleasant temperatures and fewer tourists, making it easier for you to experience tranquility while visiting this region.

Average Temperature Daytime: 20°C to 25°C - Nighttime: 10°C to 15°C

Off-Season Highlights

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November to March

The cooler months bring quieter surroundings, perfect for those seeking a peaceful retreat away from busy tourist spots.

Average Temperature Daytime: 8°C to 15°C - Nighttime: 0°C to 5°C
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Late January to February

This period features the coldest weather, providing an authentic and serene experience for visitors who prefer off-season tranquility in the area.

Average Temperature Daytime: 8°C to 12°C - Nighttime: 0°C to 3°C

Weekly Weather Forecast for Montemassi

How to Book Your Montemassi 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 Montemassi

More Top-Rated Rentals by Owner in Montemassi 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 a private outdoor swimming pool to cool off during warm Tuscan days.
  • Take advantage of spacious outdoor patios with seating areas for relaxing and dining al fresco.
  • Make the most of outdoor barbecues or grilling stations for memorable meals under the sun.
  • Benefit from beautifully maintained gardens and landscaped grounds that enhance your outdoor experience.
  • Relax in cozy outdoor lounge areas designed for unwinding amidst the scenic countryside.
  • Utilize outdoor dining spaces perfect for enjoying meals with views of the rolling hills.
  • Explore nearby walking trails or outdoor activities that showcase the natural beauty of this destination.

Top Attractions Around Montemassi

What attractions are nearby?

Nearby, you can explore scenic walking trails, indulge in wine tastings at local vineyards, or discover historic sites that showcase the rich cultural heritage of this charming region.

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Family Activities

  • Visit the Montemassi Fortress: Explore this historic fortress with your family to enjoy panoramic views and learn about the area's medieval history.
  • Discover local vineyards and farms: Engage in family-friendly tours of nearby vineyards and farms, where you can taste regional produce and experience authentic Tuscan agriculture.
  • Enjoy outdoor activities at nature reserves: Take advantage of scenic hiking trails and picnic spots in the surrounding natural reserves, perfect for a day of adventure and relaxation.
  • Participate in cultural workshops: Join local artisans' workshops that offer hands-on experiences such as pottery or cooking classes, ideal for engaging the whole family in regional traditions.
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Adult Activities

  • Wine Tasting Tours: Explore the renowned local wineries, sampling exquisite Tuscan wines that define this region's rich viticultural heritage.
  • Historic Castle Visits: Discover ancient castles and fortresses in the area, immersing yourself in the region’s medieval history and architecture.
  • Cooking Classes: Participate in authentic Tuscan cooking experiences, learning to prepare traditional dishes using fresh regional ingredients.
  • Nature Hiking Trails: Enjoy scenic hikes through the rolling landscapes and countryside, offering breathtaking views of the region’s natural beauty.

Other Places to Stay in Montemassi

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Montemassi Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Arrival Timing: Arrive during the early part of the day to settle into your rental and enjoy a relaxed exploration of the charming surroundings.
  • Explore Locally-Owned Eateries: Savor authentic Tuscan cuisine at family-run restaurants and markets nearby, enhancing your immersion in the region's culinary traditions.
  • Discover Hidden Gems: Venture beyond the main attractions to find secluded spots and scenic views that capture the true essence of this destination.
  • Connect with Your Host: Engage with your rental owner for personalized tips and local insights, making your stay more enriching and memorable.

Transportation Options

  • Car Rental Services: Renting a car gives you the flexibility to explore the scenic countryside and historic sites at your own pace, making it a popular choice for visitors staying in this part of Tuscany.
  • Local Bus Transport: The regional bus network offers affordable and convenient transportation options to travel between key towns and attractions nearby without the need for personal vehicle ownership.
  • Private Transfers: Private shuttle services and transfers are available for direct, comfortable travel from major airports and train stations to your rental in the area.
  • Taxis and Rideshare Options: Taxis and rideshare apps provide quick, reliable transportation within the region, ideal for short trips or when planning spontaneous excursions.

Local Customs Options

  • Respect for Local Traditions: You’ll find that honoring age-old customs, such as traditional festivals and local celebrations, enhances your authentic experience here in the region.
  • Dining Etiquette: Engaging politely during meals and trying local Tuscan specialties is appreciated, reflecting the area's rich culinary heritage.
  • Dress Code for Religious Sites: When visiting churches or religious landmarks, modest attire is expected to show reverence for the area's spiritual traditions.
  • Celebrating Festivals: Participating respectfully in seasonal festivals and community events offers a deeper connection with the area’s cultural identity.

Frequently Asked Questions About Montemassi Rentals by Owner

1. What are the top vacation rentals in Montemassi?

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 133 in the Montemassi 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 Montemassi. 

3. What is the cancellation policy for private rentals in this region?

Cancellation policies vary by owner, so it's important to review the specific listing details or contact the owner directly when booking your rental here in Tuscany.

4. How do I confirm availability for a rental by owner in this destination?

Availability can be checked instantly through the listing on the Rent By Owner platform, or you can reach out directly to the owner for real-time updates.

5. Are there any additional fees I should be aware of when booking a rental in this area?

Additional fees such as cleaning, service charges, or security deposits are specified in each listing. Review these details carefully or ask the owner for clarification before completing your reservation.

6. What amenities and features are typically included in rentals here?

Most rentals by owner in the region offer amenities like Wi-Fi, parking, kitchens, and outdoor spaces. To see what’s available, check the property description or contact the owner directly.

7. How far in advance should I book to secure my preferred rental in this destination?

It's recommended to book several months in advance, especially during peak seasons, to ensure availability. For specific dates, consult the listing or contact the owner to confirm.

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More Top-Rated Rentals by Owner in Montemassi Area