Discover Your Ideal Sasso di Simone, Sestino, Tuscany, Marche, Italy Vacation Rentals for an Unforgettable Stay
Discover Your Perfect Sasso di Simone Vacation Homes
Best Vacation Homes in Sasso di Simone
- Parking
- Pet Friendly
- Security/Safety
- Parking
- Pet Friendly
- View
- Parking
- Pool
- Balcony/Terrace
- Parking
- TV
- Balcony/Terrace
- Parking
- Pet Friendly
- View
- Parking
- Balcony/Terrace
- Security/Safety
- Parking
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Pet Friendly
- Security/Safety
- Bedding/Linens
- Pet Friendly
- TV
- Child Friendly
- Pet Friendly
- Balcony/Terrace
- Child Friendly
Why Choose Rent By Owner for your Sasso di Simone Vacation Rental Homes?
What makes our Vacation Rentals special?
Best Times to Visit Sasso di Simone
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider visiting during the shoulder seasons when the area's natural beauty is at its peak and the weather is ideal for exploring this charming destination in Italy.
Peak Season Highlights
Summer (June to August)
During the warm summer months, the region experiences peak activity, making it an ideal time for exploring outdoor activities and enjoying the scenic landscapes.
Autumn (September to October)
Early autumn offers pleasant weather and vibrant colors, attracting visitors seeking a culturally rich and comfortable visit in this part of Italy.
Off-Season Highlights
Winter (December to February)
The colder winter season sees fewer travelers, providing a peaceful setting perfect for relaxing in cozy accommodations while enjoying the quiet beauty of the area.
Spring (March to May)
Late winter through early spring offers a serene atmosphere with blooming nature, ideal for those looking to avoid crowds and experience the region’s natural charm.
Weekly Weather Forecast for Sasso di Simone
How to Book Your Sasso di Simone Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Sasso di Simone
Common Vacation Rentals 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 spacious outdoor terrace or patio to relax and take in the scenic views.
- Take advantage of a private garden or landscaped yard for outdoor dining or peaceful strolls.
- Make use of an outdoor barbecue grill to prepare delicious meals amid nature.
- Relax beside a private swimming pool, perfect for cooling off during warm days.
- Explore nearby hiking trails or walking paths that showcase the area's natural beauty.
- Benefit from ample parking space for your convenience during your stay.
- Experience outdoor recreational facilities such as a tennis court or playground, ideal for active days.
Top Attractions Around Sasso di Simone
What attractions are nearby?
Within this charming region, you can explore scenic hiking trails, discover local culinary delights, and enjoy tranquil countryside views—all just a short distance from your vacation rentals here in Sasso di Simone, Sestino, Tuscany, Marche, Italy.

Family Activities
- Exploring Sestino's historic center: Take a family walk through the charming streets of this local town and discover its medieval architecture and cultural heritage.
- Hiking in the surrounding hills: Enjoy scenic hikes with panoramic views of the lush landscape that surrounds this part of Tuscany and Marche, perfect for outdoor family adventures.
- Visiting nearby farms and agriturismos: Experience authentic regional cuisine and farm life by touring local farms, ideal for engaging children with rural traditions.
- Participating in nature excursions: Discover the diverse flora and fauna on guided nature walks, providing educational fun for the entire family in this tranquil setting.
Adult Activities
- Hiking and Nature Walks: Explore scenic trails with panoramic views that showcase the stunning landscapes of this region, perfect for leisurely walks or more vigorous hikes.
- Wine Tasting Tours: Discover local wines at nearby vineyards, immersing yourself in the area's rich viticultural tradition and enjoying tastings in charming settings.
- Historical Site Visits: Visit ancient ruins and historic landmarks that tell the story of the area's cultural heritage and preserved architecture.
- Cooking Classes: Experience authentic regional cuisine firsthand by participating in cooking classes that highlight the flavors of Tuscany and Marche.
Sasso di Simone Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Take the opportunity to savor authentic regional dishes at local eateries to enrich your stay in this scenic area.
- Visit Off-the-Beaten-Path Sites: Discover hidden gems and lesser-known spots around here to experience a more authentic and memorable visit.
- Plan for Nature Activities: Make the most of the picturesque landscape by engaging in outdoor pursuits like hiking or leisurely walks through the surrounding countryside.
- Connect with the Community: Engage with locals to gain insider tips and insights that can deepen your appreciation for this peaceful destination.
Transportation Options
- Car Rental Services: Renting a car offers the most flexibility for exploring this region's scenic countryside and charming villages at your own pace.
- Public Bus Transport: Local bus services connect you to nearby towns and attractions, providing an affordable and convenient way to navigate here.
- Taxi and Private Transfers: For direct and comfortable travel, taxis and private transfer options are available, ensuring seamless trips from airports or stations to your vacation rental.
- Shuttle Services: Some accommodations provide shuttle services within the area, making it easy to visit local points of interest without hassle.
Local Customs Options
- Respect for Religious Traditions: You’ll notice that locals observe religious customs with great reverence, especially during celebrations associated with the region’s historic churches and festivals.
- Local Cuisine Etiquette: When dining here, it’s customary to enjoy regional dishes with a sense of appreciation, often sharing meals in a communal style that reflects the area's strong culinary traditions.
- Preservation of Historical Heritage: Visitors are encouraged to honor the local customs of conserving historical sites and participating respectfully during cultural events.
- Traditional Handcrafts and Festivals: Engaging in or observing craft-making and festivals offers a glimpse into the region’s rich heritage, which remains a vital part of daily life here.
Frequently Asked Questions About Sasso di Simone?
1. What are the top vacation rentals in Sasso di Simone?
There are a lot of options in Sasso di Simone. If you plan on staying in the Sasso di Simone area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Sasso di Simone:
- Pretty Farmhouse with pool
- Relax in Nature: Holiday Home with a View in Tuscany
- Rustic stone house in Romagna with panoramic terrace and free Wi-Fi
- Appartamentino Rustico in Villa Maindi with garden use and free WiFi
- Carpegna Town Suites
- Farmhouse in Tuscany with Pool and Barbecue
- Tuscan Hillside Heaven
- Hotel Ulisse
- Country House "Locanda Le Querce"
- Carpegna Town Suites
2. How many Rentbyowner vacation rentals are available in Sasso di Simone?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 18 in the Sasso di Simone 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 Sasso di Simone.
3. What is the cancellation policy for vacation rentals in this area?
4. Are there any additional fees I should be aware of when booking a rental here?
5. How do I secure my booking for a vacation rental in this destination?
6. Is it possible to modify or cancel my reservation after booking?
7. What amenities are typically included in vacation rentals in this region?
Best Vacation Homes in Sasso di Simone
- Pet Friendly
- TV
- Balcony/Terrace
- Pet Friendly
- TV
- Balcony/Terrace
- Parking
- TV
- Balcony/Terrace