Ossaia vacation rentals

We found 1,360 vacation rentals — enter your dates for availability

Discover a selection of 7 homes and other vacation rentals in Ossaia that are perfect for your trip. Vacation homes provide the best amenities for your stay with friends, family, or just your pet, such as WiFi and a fireplace. At the end of the day, you'll find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Ossaia

Showing deals for:Apr 17 - Apr 24

Image gallery for Private Pool Villa near Cortona. Secluded, Perfect for Families.

Pool
9.8 out of 10, Exceptional, (59 reviews)
Exceptional
(59 reviews)

Private Pool Villa near Cortona. Secluded, Perfect for Families.

Toscana

9% off
Price is $634
$4,440 for 7 nights
All fees included
Private Pool Villa near Cortona. Secluded, Perfect for Families.

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Find out more about Ossaia

Why visit Ossaia

  • Charming village atmosphere: Experience the friendly and romantic vibe of Ossaia, perfect for relaxation and exploration.
  • Cultural sites: Visit stunning churches and a historical Roman villa to immerse yourself in local history.
  • Beautiful piazzas: Enjoy leisure time in picturesque squares, ideal for soaking in the local culture.
  • Outdoor activities: Discover serene lakes nearby, perfect for scenic walks and family outings.
  • Diverse accommodations: Choose from luxurious villas to cozy apartments, ensuring a comfortable stay.

Popular types of accommodation in Ossaia

Planning a getaway to Ossaia? The excitement begins with selecting the perfect place to stay. From luxurious villas and cozy houses to comfortable apartments, Ossaia offers a variety of accommodations to suit every traveler. Enjoy top-notch amenities, spacious dining areas, and the comforts of home in your holiday rental. Discover your ideal vacation home and make unforgettable memories in this charming destination.

  • Villas: The top choice for travelers seeking luxury, these spacious accommodations offer stunning views and private amenities in Ossaia.
  • Houses: Ideal for families or groups, these homes provide a comfortable and personalized experience during your stay.
  • Apartments: Perfect for couples or solo travelers, these cozy spaces offer the convenience of home in a vibrant setting.
  • Cottages: These charming retreats provide a quaint and intimate atmosphere, great for those looking to unwind.
  • Agritourism: Experience the countryside with these unique stays that combine agriculture and hospitality for a taste of local culture.**

Top attractions near Ossaia

Ossaia, located in the beautiful Cortona region of Tuscany, offers a perfect blend of culture and outdoor experiences for families, business travelers, and city explorers alike. You can visit stunning churches, relax in charming piazzas, and enjoy the serene lakes nearby. Additionally, don't miss the opportunity to explore a Roman villa, which adds a unique historical touch to your visit. Ossaia is sure to provide an unforgettable Italian vacation experience.

  • Lake Trasimeno: Discover the serene beauty of Lake Trasimeno, located 9 miles from Ossaia. Enjoy its sandy beaches, picturesque scenery, and romantic outdoor activities, perfect for relaxation and adventure.
  • Villa Bramasole: A historic gem just 3 miles away, Villa Bramasole offers a glimpse into local culture. This charming estate is renowned for its stunning architecture and rich history, making it a must-see.
  • Piazza della Repubblica: Experience the vibrant atmosphere of Piazza della Repubblica, situated 3 miles from Ossaia. This lively square is a cultural hub, surrounded by cafes and shops, ideal for soaking in city life.

Things to do recommended for couples

For a romantic getaway in Ossaia, visit Fattoria Le Capezzine for wine tasting and outdoor fun, indulge in luxury at Tennis Club Castiglionese, or unwind at the serene Terme di Chianciano spa. Each experience offers a unique touch to your couple's retreat in Tuscany.

Things to do recommended for families

Families vacationing in Ossaia can have a splashing good time at Tavernelle Aquatic Park, located 17 miles away. This waterpark offers a variety of entertainment and adventure activities, making it a perfect spot for family fun and lasting memories.

Things to do recommended for groups

Experience the local charm of Ossaia by shopping at the Valdichiana Outlet Village, just 10 miles away, or enjoy a captivating performance at the Signorelli Theatre, 3 miles from town. For adventure seekers, hike Hannibal's Journey for stunning outdoor scenery, also 3 miles away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Ossaia

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips just for you.

  • Traveling to Ossaia with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all of these options, and more, on Vrbo.
  • Traveling to Ossaia with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with having suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Ossaia: For many families, a vacation isn't truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Ossaia: If you're searching for vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly locate and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Ossaia

Ossaia, a charming village in Cortona, Tuscany, offers a delightful mix of relaxation and exploration. You can enjoy beautiful vacation homes and local spas while soaking in the friendly, romantic atmosphere. Nearby cities invite you to experience rich history and vibrant neighborhoods, perfect for family or business retreats. With stunning properties and rave reviews, your stay in Ossaia will be filled with memorable excursions and the essence of Tuscany.

  • Cortona: Nestled in the picturesque hills of Tuscany, Cortona is a charming city that beckons travelers seeking outdoor adventures, romantic escapades, and rich cultural experiences. The city offers a delightful mix of ancient history and modern comforts, with attractions such as historic landmarks, scenic bridges, and the beautiful nearby lake. Visitors can indulge in spa treatments and enjoy theatrical performances, making it a perfect destination for relaxation and cultural enrichment.
  • Riccio: Just 0.6 miles from Ossaia, Riccio is a quaint village that provides a serene escape with its stunning scenery and inviting beaches. Ideal for couples looking for a romantic getaway, Riccio boasts lovely views of the surrounding landscape and easy access to the tranquil lake. This charming village is perfect for leisurely strolls along the waterfront, soaking up the sun, and enjoying the local atmosphere.
  • Tuoro sul Trasimeno: Located approximately 4 miles from Ossaia, Tuoro sul Trasimeno is a vibrant city known for its outdoor activities and scenic beauty. Travelers can explore its beautiful lakeside setting while indulging in spa treatments or enjoying a day at the amusement park. The area is rich in history, featuring hot springs and historic sites that add to its allure. Whether you're seeking adventure or relaxation, Tuoro sul Trasimeno offers a delightful blend of experiences.

Best time to go to Ossaia

If you're planning a trip to Ossaia, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January39.0°F (3.9°C)Light RainMostly CloudyLowAverage
February41.2°F (5.1°C)Light RainMostly SunnyLowSlightly Low
March46.0°F (7.8°C)Light RainMostly SunnyAverageSlightly Low
April52.7°F (11.5°C)Light RainMostly SunnyAverageAverage
May59.5°F (15.3°C)Light RainMostly SunnyAverageAverage
June69.1°F (20.6°C)Light RainMostly SunnyAverageSlightly High
July74.8°F (23.8°C)No Rain (Dry)SunnyHighSlightly High
August74.5°F (23.6°C)No Rain (Dry)SunnyHighSlightly High
September65.7°F (18.7°C)Light RainMostly SunnyHighAverage
October56.8°F (13.8°C)Light RainMostly SunnyAverageAverage
November48.6°F (9.2°C)Light RainMostly SunnyAverageSlightly Low
December41.5°F (5.3°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner definitely has its perks. When you enroll in our travel rewards program, One Key, you can immediately access member discounts and earn OneKeyCash on eligible reservations. Sign up now and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's user-friendly Trip Board offers you a convenient place to plan new trips, pick up right where you left off, or review and organize your travel arrangements. You can easily find the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Book a vacation rental for your Ossaia getaway

Experience the unique character of Ossaia with a stay in a vacation home rental. You'll find plenty to explore during your stay in the area. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Ossaia

Are you hoping to discover things to do in the city? Venture out of your cozy vacation rental and check out everything that Ossaia has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • La Braccesca Winery (5.3 mi / 8.6 km)
  • Fattoria Le Capezzine (5.5 mi / 8.8 km)
  • Magione Racetrack (13.8 mi / 22.2 km)
  • Cantina Contucci (14.9 mi / 23.9 km)
  • Consorzio del Vino Nobile di Montepulciano (14.9 mi / 23.9 km)
  • Tennis Club Castiglionese (8.3 mi / 13.4 km)

Exploring the natural features in Ossaia

Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Ossaia. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Isola Maggiore (6 mi / 9.6 km)
  • Lake Trasimeno (8.5 mi / 13.7 km)
  • Chiusi Lake (12.5 mi / 20.1 km)
  • Val di Chiana (13.9 mi / 22.4 km)
  • Terme di Montepulciano Spa (15 mi / 24.2 km)
  • Hannibal's Journey (2.9 mi / 4.6 km)

Traveling to and around Ossaia

The nearest airport is in Sant Egidio Airport (PEG), located 26.9 mi (43.3 km) from the city center.

Frequently asked questions

What is the best area to stay in Ossaia when booking a vacation rental?
When looking for a vacation rental in Ossaia, Tuscany, one of the best areas to consider is the charming neighborhood surrounding the historic center. This area not only offers a picturesque setting filled with rustic charm but also provides convenient access to local attractions. Staying here places you close to the renowned Villa Bramasole, famously depicted in Frances Mayes' book "Under the Tuscan Sun." This villa is a beautiful example of Tuscan architecture and is surrounded by stunning landscapes that capture the essence of the region.

Another appealing aspect of this neighborhood is its proximity to the medieval town of Cortona, which is just a short drive away. Cortona boasts narrow cobblestone streets, quaint shops, and breathtaking views of the surrounding countryside. The area typically features a good selection of vacation rental properties, making it easy to find accommodations that fit your needs, whether you're looking for a cozy apartment or a larger villa.

Choosing to stay in this part of Ossaia not only immerses you in the local culture but also provides a great base for exploring the wider Tuscany region.
How much does it cost to rent a vacation home in Ossaia?
Prices for vacation rentals in Ossaia vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Ossaia to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Ossaia vacation house rentals?
You can find great discounts on house rentals in Ossaia on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay vacation rentals in Ossaia?
A long-stay vacation rental in Ossaia is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Ossaia vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Ossaia with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
How early should I book a Ossaia vacation rental?
Book your Ossaia vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Ossaia?
In Ossaia, Tuscany, visitors can take part in the charm of the region's picturesque countryside. The nearby town of Cortona, known for its well-preserved medieval architecture, offers attractions such as the Diocesan Museum and the stunning views from the Piazza della Repubblica. Vacation rentals in Ossaia often provide a serene escape while still being a short drive from Cortona's vibrant atmosphere and local eateries.

For those interested in enjoying nature, the surrounding hills and vineyards are superb for hiking and wine tasting, making it an ideal spot for experiencing the Tuscan landscape. Additionally, the scenic Lake Trasimeno is just a bit further away, providing opportunities for water activities and leisurely lakeside walks.
Can I change or cancel my Ossaia home rental booking on Vrbo?
To find Ossaia vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Ossaia vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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