Discover Your Perfect San Filippo Vacation Homes

San Filippo Luxury Rentals

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Why Choose Rent By Owner for your San Filippo Vacation Rental Homes?

What makes our Vacation Rentals 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 San Filippo

When should you plan your Vacation Rentals stay?

To make the most of your stay, consider visiting during the shoulder seasons when the region offers pleasant weather and fewer crowds, allowing you to fully enjoy the authentic charm of this destination.

Peak Season Highlights

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Late Spring (May to June)

During the late spring months, this region enjoys warm weather and lush landscapes, making it ideal for exploring the countryside and enjoying outdoor activities. Booking your vacation rental here during this time ensures a vibrant atmosphere with longer daylight hours.

Average Temperature Daytime: 22°C to 26°C - Nighttime: 11°C to 15°C
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Early Fall (September to October)

The early fall offers pleasant temperatures and fewer crowds, providing a peaceful environment to experience the area's natural beauty and local culture. Securing your stay during these months allows you to enjoy mild weather and scenic vistas in comfort.

Average Temperature Daytime: 20°C to 24°C - Nighttime: 9°C to 13°C

Off-Season Highlights

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Winter (December to February)

In winter, the region becomes quieter, offering an intimate setting for cozy stays and cultural exploration without the bustling tourist crowds. This is a great time to explore inland attractions while enjoying cooler temperatures.

Average Temperature Daytime: 7°C to 12°C - Nighttime: 0°C to 4°C
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Early Spring (March to April)

Early spring marks the transition into warmer weather, though it remains relatively quiet, making it suitable for visitors who prefer a more relaxed experience. You can enjoy the blossoming scenery and serene surroundings at this time of year.

Average Temperature Daytime: 12°C to 16°C - Nighttime: 3°C to 7°C

Weekly Weather Forecast for San Filippo

How to Book Your San Filippo Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. 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 San Filippo

More Top-Rated Vacation Rentals in San Filippo Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 relax and cool off amidst the stunning Tuscan landscape.
  • Take advantage of spacious gardens or courtyards perfect for outdoor dining and gatherings.
  • Benefit from well-maintained patios or terraces offering panoramic views of the rolling hills.
  • Make use of outdoor barbecue facilities to prepare authentic Italian meals with family or friends.
  • Stroll through scenic walking paths or landscaped grounds surrounding your rental property.
  • Utilize outdoor furniture such as loungers and umbrellas to unwind in the sun.
  • Participate in outdoor activities like playing lawn games on expansive grassy areas.

Top Attractions Around San Filippo

What attractions are nearby?

In this charming region, you can explore scenic hiking trails, indulge in local wine tastings, and immerse yourself in the authentic Tuscan countryside, all just moments from your preferred vacation rentals here in San Filippo, Barberino Tavarnelle.

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Family Activities

  • Visit the Countryside Nature Trails: Embark on family-friendly walks along scenic trails that wind through lush landscapes, offering a peaceful way to experience the natural beauty of this region.
  • Explore Local Wineries and Olive Oil Tastings: Enjoy guided tours suitable for families, where you can learn about traditional production methods while sampling regional wines and olive oils.
  • Discover Historical Villas and Gardens: Tour charming estates with expansive gardens that provide an enchanting setting for educational outings and outdoor picnics.
  • Participate in Cooking Classes: Engage in family-focused cooking experiences that highlight Tuscan cuisine, perfect for creating memorable moments together here.
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Adult Activities

  • Wine Tasting Tours: Explore the renowned vineyards of the region through guided wine tastings that showcase the area's rich Tuscan wine heritage.
  • Cooking Classes in Tuscany: Participate in authentic Tuscan cooking classes to learn traditional recipes and immerse yourself in local culinary traditions.
  • Historical Sightseeing: Discover the area's medieval villages and historic landmarks that offer a glimpse into its fascinating past.
  • Hiking and Nature Walks: Enjoy scenic trails through the rolling hills and lush landscapes surrounding here, perfect for outdoor enthusiasts seeking tranquility and natural beauty.

San Filippo Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the local vineyards: Take time to visit nearby wineries and enjoy authentic tastings that showcase the region’s renowned wine production.
  • Embrace regional cuisine: Savor traditional Tuscan dishes at local trattorias to truly experience the flavors of this picturesque area.
  • Discover scenic routes: Use scenic drives or walking trails to immerse yourself in the countryside’s beauty and capture memorable photos.
  • Engage with local culture: Attend regional events or markets to gain insight into the area’s rich history and vibrant community life.

Transportation Options

  • Car Rental Services: Renting a car provides the most flexibility to explore the scenic countryside and nearby attractions at your own pace.
  • Public Buses: Local bus routes connect this area with larger cities and towns, offering an affordable means of transportation during your stay.
  • Taxi and Ride-Sharing: Taxis and ride-sharing options are readily available here, providing convenient door-to-door service for quick trips or outings.
  • Private Transfers: Booking private transfer services ensures comfortable and reliable travel between the region and major airports or train stations.

Local Customs Options

  • Traditional Tuscan Greetings: When visiting here, it is customary to greet locals with a warm handshake or cheek kisses, reflecting the area's friendly and welcoming culture.
  • Respect for Local Festivals: Participating respectfully in regional festivals and celebrations allows you to experience the authentic customs of this destination and connect with the community.
  • Enjoying Regional Cuisine: Embracing local dining manners, such as sharing large tables during meals, helps you engage more deeply with the area's culinary traditions.
  • Preserving the Peaceful Atmosphere: Maintaining a quiet demeanor, especially during siesta hours, respects the tranquil lifestyle that characterizes the region's way of life.

Frequently Asked Questions About San Filippo?

1. What are the top vacation rentals in San Filippo?

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

2. How many vacation rentals have private pools in San Filippo?

There are 104 vacation rentals with private pools near San Filippo. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in San Filippo are best for families?

If you are looking for a family-friendly vacation home in San Filippo, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in San Filippo:

4. How many Rentbyowner vacation rentals are available in San Filippo?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 515 in the San Filippo 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 San Filippo. 

5. What is the cancellation policy for vacation rentals in this area?

The cancellation policy varies depending on the property listing. You should review the specific cancellation terms outlined in the rental details or contact the property owner directly to understand your options and any applicable fees.

6. How do I ensure my booking in Tuscany meets all requirements?

To secure your reservation, carefully read the listing description, policies, and any house rules provided. If you have questions or special requests, reaching out to the property owner can help clarify details and ensure a smooth booking process.

7. Are there additional fees or charges for staying at a vacation rental here?

Additional fees such as cleaning, security deposits, or local taxes may apply. These details are typically included in the listing or confirmed during the booking process, so reviewing the specific property information is recommended.

8. What amenities can I expect when booking a vacation rental in this part of Tuscany?

Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, and outdoor spaces. Check the detailed listing for a comprehensive list of amenities offered to ensure the rental meets your needs.

9. Is it possible to modify or extend my stay once booked?

Modification or extension policies depend on the individual property owner. Contacting the owner directly through the booking platform can help you discuss possible changes and confirm availability.