Ossaia holiday rentals

We found 1,290 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Ossaia that are perfect for your trip. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as a fireplace and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Ossaia

Showing deals for:18 Dec - 25 Dec

Exterior
Exterior
Lunch on the rear patio.
The Casa Castagni living room
Exceptional
(5 reviews)

Gorgeously restored tranquil farmhouse

Castiglione del Lago

19% off
AU$2,750
for 7 nights, 1 home
AU$393 per night
includes taxes & fees
Gorgeously restored tranquil farmhouse
Dining
Outdoor dining
Pool
Exterior
Exceptional
(6 reviews)

Apartment in Farmhouse

Cortona

6% off
AU$1,513
for 7 nights, 1 room
AU$216 per night
includes taxes & fees
Apartment in Farmhouse
Exterior
Property grounds
Outdoor dining
Pool
Exceptional
(37 reviews)

Villa Mulinoavento with magnificent view 5 minutes walking downtown

Cortona

9% off
AU$7,015
for 7 nights, 1 villa
AU$1,002 per night
includes taxes & fees
Villa Mulinoavento with magnificent view 5 minutes walking downtown
Living area
Property grounds
Pool
Stalla Private Garden with BBQ
Exceptional
(19 reviews)

Large country apartment in Cortona 3bed3bath with shared pool & gorgeous gardens

Cortona

7% off
AU$4,732
for 7 nights, 1 apartment
AU$676 per night
includes taxes & fees
Large country apartment in Cortona 3bed3bath with shared pool & gorgeous gardens
entrance
View from the outside
Dining Room
Living room + Sofa bed
Exceptional
(59 reviews)

Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"

Cortona

14% off
AU$2,371
for 7 nights, 1 home
AU$339 per night
includes taxes & fees
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
AHHH! Tuscany!
Interior
Enter here
Room
Exceptional
(11 reviews)

❤️ of Castiglion Fiorentino

Castiglion Fiorentino

9% off
AU$1,141
for 7 nights, 1 apartment
AU$163 per night
includes taxes & fees
❤️ of Castiglion Fiorentino
Take a seat. You're finally home.
There's no doubt you're in Tuscany
We've tailored every detail to help you feel at home
The master bedroom promises privacy
Exceptional
(24 reviews)

Medieval Delight! Balcony, Rustic Beams & Brick Fireplace w/Modern Amenities

Castiglion Fiorentino

9% off
AU$1,529
for 7 nights, 1 apartment
AU$218 per night
includes taxes & fees
Medieval Delight! Balcony, Rustic Beams & Brick Fireplace w/Modern Amenities
Dining
Exterior detail
Living area
Exterior
Exceptional
(15 reviews)

Ray's House - GLICINE Apartment

Passignano sul Trasimeno

8% off
AU$1,721
for 7 nights, 1 apartment
AU$246 per night
includes taxes & fees
Ray's House - GLICINE Apartment
Exterior
Outdoor dining
Dining
Pool
Exceptional
(25 reviews)

Farm on the hills of Cortona with a spectacular view of the Valdichiana Valley

Cortona

7% off
AU$2,488
for 7 nights, 1 room
AU$355 per night
includes taxes & fees
Farm on the hills of Cortona with a spectacular view of the Valdichiana Valley

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Ossaia getaway

Learn about the unique charm of Ossaia with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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 looking for top things to see and do during your stay? Venture out of your cosy holiday rental and check out everything that makes Ossaia a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Tennis Club Castiglionese (8.3 mi / 13.4 km)
  • Magione Racetrack (13.8 mi / 22.2 km)
  • Consorzio del Vino Nobile di Montepulciano (14.9 mi / 23.9 km)
  • La Braccesca Winery (5.3 mi / 8.6 km)
  • Tenuta Valdipiatta (12.8 mi / 20.5 km)
  • Naturalistic Oasis La Valle (12.8 mi / 20.6 km)

Exploring the natural features in Ossaia

Whether you're an active traveller or just want to take in the scenery, Ossaia is a great spot to appreciate mother nature. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Terme Sant'Elena (15.3 mi / 24.6 km)

Travelling to and around Ossaia

The nearest airport is in Perugia San Francesco d'Assisi – Umbria Intl. Airport (PEG), located 26.9 mi (43.3 km) from the city centre.

Frequently asked questions

What is the best area to stay in Ossaia when booking a holiday rental?
The best area to stay in Ossaia, Tuscany, is the charming neighbourhoods that surround this picturesque locale. Ossaia itself offers a tranquil atmosphere, superb for those looking to unwind amidst the stunning Tuscan landscape. While the area is relatively small, it boasts a selection of delightful properties that capture the essence of Italian living, with many featuring beautiful views of the rolling hills.One of the top attractions nearby is the historic city of Cortona, known for its Etruscan heritage and breathtaking vistas. Visitors can explore the cobbled streets, visit the Diocesan Museum, or relax in the beautiful gardens of the town. Additionally, the region is renowned for its vineyards and olive groves, making it an ideal spot for wine enthusiasts to indulge in local tastings.In terms of local amenities, Ossaia is conveniently located, allowing easy access to nearby services while still providing a peaceful retreat. With a variety of properties available, holidaymakers can find accommodations that suit their preferences, ranging from quaint apartments to larger villas, all within reach of the stunning attractions that Tuscany has to offer.
What are the top attractions in Ossaia?
In Ossaia, Tuscany, visitors can experience a blend of natural beauty and cultural heritage. The nearby town of Cortona is a highlight, renowned for its stunning views over the Valdichiana and rich Etruscan history. Here, one can explore the charming streets, visit the Diocesan Museum, and admire the beautiful Basilica of Santa Margherita.Additionally, the surrounding countryside offers picturesque landscapes great for hiking and cycling. The area is dotted with vineyards and olive groves, making it ideal for wine and olive oil tasting experiences. For those interested in art, the Etruscan Academy Museum in Cortona showcases a fascinating collection of ancient artefacts.
Are all fees included in the Ossaia holiday homes prices shown on Stayz?
Stayz 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.
Are there any Ossaia holiday homes with parking?
Stayz offers a wide selection of holiday homes in Ossaia with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Ossaia holiday homes?
You can find great discounts on holiday homes in Ossaia on Stayz, 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 change or cancel my Ossaia holiday home booking on Stayz?
To find Ossaia holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Ossaia?
A long-stay holiday home in Ossaia is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Ossaia holiday home?
Book your Ossaia holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Ossaia?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Ossaia to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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