Discover Your Perfect Ossaia Vacation Homes

Ossaia Large Vacation Homes

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10.0 (2 Reviews)
Apartment
B&B Cortona Suite - Together in Tuscany
  • Air Conditioner
  • Security/Safety
  • Child Friendly
View Availability
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10.0 (1 Review)
Villa
Le Caselle 26, Emma Villas
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
See More Family Vacation Rentals in Ossaia on FVR

Why Choose Rent By Owner for your Ossaia 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 Ossaia

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience of the region's charming atmosphere and pleasant weather, ensuring you enjoy the best moments during your stay in this beautiful destination.

Peak Season Highlights

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Spring (April to June)

During spring, the area blossoms with vibrant colors and pleasant weather, making it an ideal time for exploring the picturesque countryside.

Average Temperature Daytime: 20°C to 25°C - Nighttime: 10°C to 15°C
autumn
Autumn (September to October)

Autumn offers mild temperatures and stunning fall foliage, perfect for enjoying the region's scenic beauty without the summer crowds.

Average Temperature Daytime: 20°C to 22°C - Nighttime: 10°C to 12°C

Off-Season Highlights

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Winter (December to February)

Winters are quiet and cooler, providing a cozy atmosphere for those seeking tranquility and a quieter experience in this destination.

Average Temperature Daytime: 8°C to 12°C - Nighttime: 0°C to 5°C
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Late Autumn (November)

Late autumn sees fewer visitors and cooler temperatures, offering a peaceful retreat amid the natural beauty of the region.

Average Temperature Daytime: 12°C to 15°C - Nighttime: 5°C to 8°C

Weekly Weather Forecast for Ossaia

How to Book Your Ossaia 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 Ossaia

More Top-Rated Vacation Rentals in Ossaia 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 under the Tuscan sun.
  • Take advantage of outdoor dining areas perfect for al fresco meals amid scenic views.
  • Stroll through beautifully landscaped gardens designed for your leisure and tranquility.
  • Utilize spacious patios or terraces ideal for morning coffee or evening gatherings.
  • Make use of barbecue facilities to prepare traditional Tuscan cuisine with family and friends.
  • Benefit from ample parking spaces in secure outdoor settings.
  • Experience scenic outdoor seating areas that offer panoramic views of the surrounding countryside.

Top Attractions Around Ossaia

What attractions are nearby?

Within this charming region, you can enjoy exploring local wineries, discovering historic towns, and savoring authentic Tuscan cuisine just a short drive from your vacation rental in Ossaia, Cortona, Tuscany.

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Family Activities

  • Exploring Cortona's Historic Center: Discover the charming streets and ancient architecture that make this area a captivating experience for families seeking cultural enrichment.
  • Visit to the Etruscan Museum: Engage your family with fascinating exhibits showcasing the region’s ancient Etruscan heritage, offering educational fun for all ages.
  • Outdoor Picnics in Local Parks: Relax and enjoy quality time together in scenic parks nearby, perfect for outdoor dining and play amid nature.
  • Walking Tours of the Tuscan Countryside: Embark on family-friendly strolls through rolling hills and picturesque landscapes, immersing yourselves in the region’s natural beauty.
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Adult Activities

  • Wine Tasting Tours: Discover the rich flavors of Tuscany through wine tasting experiences at local vineyards nestled just outside here, offering a perfect way to indulge in regional specialties.
  • Cultural Heritage Visits: Explore the area's historic churches and museums that showcase the region’s captivating history and art, ideal for enriching your stay in this destination.
  • Cooking Classes: Participate in authentic Tuscan cooking classes that highlight traditional recipes, allowing you to bring home a piece of this culinary tradition.
  • Scenic Hiking Trails: Take advantage of scenic hiking routes through the countryside, providing breathtaking views and a peaceful retreat within the natural beauty of the region.

Ossaia Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local cuisine: Take the opportunity to indulge in authentic Tuscan dishes at nearby eateries, enhancing your stay with traditional flavors unique to this region.
  • Visit nearby cultural sites: Make the most of your visit by exploring charming villages and historical landmarks within easy reach from here, immersing yourself in the area's rich heritage.
  • Plan outdoor activities: Enjoy the scenic countryside with leisurely walks or cycling adventures that showcase the natural beauty of this destination.
  • Utilize local markets: Shop at regional markets for fresh produce and handcrafted goods, offering a genuine taste of the area's vibrant community life.

Transportation Options

  • Car Rentals: Renting a car is an ideal way to explore the region at your own pace, giving you easy access to nearby towns and scenic countryside around Ossaia, Cortona.
  • Bus Services: Local bus transportation offers a cost-effective and convenient option for getting around here, connecting you with key destinations within Tuscany.
  • Private Transfers: Private transfer services provide reliable and comfortable transportation, making your journey from airports or nearby cities seamless and stress-free.
  • Taxis and Ridesharing: Taxis and ridesharing options are readily available for quick trips within the area, ensuring you can easily reach your vacation rentals in Cortona without hassle.

Local Customs Options

  • Local Festivals and Traditions: During special occasions, you can enjoy authentic Tuscan festivals that celebrate regional history, food, and art, offering a glimpse into the area's rich cultural heritage.
  • Religious Celebrations: Participating in local religious processions and church festivals provides an immersive experience of the community’s spiritual life here.
  • Traditional Cuisine:** Sampling regional dishes often involves local customs like family-owned trattorias serving recipes passed down through generations, giving you a taste of genuine Tuscan flavors.
  • Handicrafts and Local Markets: Visiting markets where artisans sell handmade products offers insight into traditional crafts that have been preserved over centuries in this part of Tuscany.

Frequently Asked Questions About Ossaia?

1. What are the top vacation rentals in Ossaia?

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

2. How many vacation rentals have private pools in Ossaia?

There are 212 vacation rentals with private pools near Ossaia. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Ossaia are best for families?

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

4. How many Rentbyowner vacation rentals are available in Ossaia?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 974 in the Ossaia 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 Ossaia. 

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

Cancellation policies vary by property, so it's important to review the specific listing details or contact the owner directly to understand the terms and any applicable fees.

6. How do I secure my reservation for a vacation rental in this destination?

Reservations are typically confirmed through the booking platform once your selected dates and payment details are completed; always confirm the process with the property owner if you have special requests.

7. Are there any house rules or restrictions I should be aware of before booking?

Each property has its own set of house rules listed in the rental description, including policies on pets, smoking, or noise; review these carefully before confirming your reservation.

8. What amenities are generally available at vacation rentals here?

Amenities can vary, but many properties offer features such as Wi-Fi, fully equipped kitchens, private outdoor spaces, and parking; check each listing for a detailed amenities list.

9. Is it possible to see recent reviews from previous guests before booking?

Yes, guest reviews are usually available on the listing page, providing insights into the property’s condition, location, and overall guest experience for this region.