
Vacation rentals in Ossaia
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Ossaia
Guests agree: these stays are highly rated for location, cleanliness, and more.

La Pergola, a beautiful Tuscan farmhouse
Villa La Pergola, a recently built house, together with other near villas is part of a small residential area situated in wordeful hilly position surrounded by greenery and spotted with olive groves. The façade is enhanced by the stone patio from which one can enjoy a stunning view on the valley underneath. On the several levels in the outer space there is the swimming pool, an outer cooking space with BBQ and wood-burning oven and, on the lower level, a covered park (1 car). The house, sleeping up to 8 people, is developed on four floors. On the ground floor the sunny living area gives access to the garden both from the sitting room with sofa and fireplace and the fully-equipped kitchen, connected to the pergola, ideal to comfortably eat in the open air. On the same floor there is also a double bedroom and a bathroom with shower. 2 double bedrooms, each with private bathroom, are located on the first floor from which it is possible to enjoy an evoking view on the Valdichiana. An additional twin bedroom (1 French and 1 single) with bathroom with tub, ideal for kids, is at guests' disposal in the attic. All the windows are equipped with mosquito nets and all rooms dispose of air conditioning. Cotona is only 5 km far, while within 2 km there are supermarkets and main amenities. Villa La Pergola is ideal for those who want to spend a pleasant holiday in Tuscany.

Apt. Silvana-Tenuta VillaAugusto
The property is located in a residential area 3/4 km from the center of Cortona. Surrounded by greenery, a true paradise of tranquility. Independent and welcoming accommodation with large spaces furnished with antique furniture and objects, equipped kitchen, 2 bedrooms (double and 2 single), 1 bathroom. Air-conditioned rooms. Outdoor space equipped with table, chairs and sun loungers. Large park with many shaded areas and large swimming pool (14x7) surrounded by greenery, shared with other guests of the estate.

Cortona’s Rooftop Nest
The apartment is located in the historic center right in front of the wonderful church of San Francesco and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It accommodates 4 people. Fans in the bedrooms The apartment is located in the historic center right in front of the wonderful church of St. Francis and a few steps from the main square. Furnished in a country chic style and equipped with all comforts. It can accommodate up to 4 people. Fans in the rooms.

Tuscan charm of villa - countryside - Villa Senaia
In the charming Tuscan countryside, among olive trees and vineyards, a stone villa, in a strategic position to grasp the secrets of Tuscany and Umbria air conditioning and swimming pool with wellness area for your relaxation and comfort Villa Senaia is a large house with wooden beams, in a beautiful hillside location with idyllic views overlooking one of the favorite places in the Tuscan countryside, an attractive setting for outdoor dining, drinking Tuscan wine and listening to crickets and cicadas

Historic Villa Getaway with 6BR/9BA, Pool, Views
This six-bedroom villa complex, set in atop a hill, overlooks a panorama of surrounding hills, fully immersed in nature. Villa was estored in 2020, with the rustic flair preserved to maintain its unique charm. The authentic stonework, the open fireplace in the entrance hall, and the exposed beams are in harmony with wooden floors. The villa is within 30min drive of Cortona. Also near Siena, Gubbio, Assisi, Lake Trasimeno, Arezzo, Montepulciano, Spoleto, and Perugia. (Read other details to note)

Rural Tuscany | Family farmstay with restaurant
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

Stunning Tuscan Villa & Panoramic Infinity Pool
Stunning Tuscan hilltop Villa, with infinity edge swimming pool, has sweeping 180° panoramic views to Cortona, Lake Trasimeno and the entire Val Di Chiana. The perfect family retreat within ancient sun-drenched olive groves. 5 Double bedrooms; 4 bathrooms; new fully integrated kitchen & dining living space; living room with fireplace; TV snug; stone BBQ & outdoor kitchen within dining terraces and gardens; covered breakfast porch; parking; private infinity pool with sunset views.

Villa Tonacato - Charming Villa with private pool
An old rural farmhouse, located in the Tuscan hills overlooking the surrounding countryside. Isolated and ideal for those who want to relax but close to the main Italian tourist cities. Each room is equipped with air conditioners with windfree technology, in the living room there is an 82" ULTRA HD TV with SKY and international channels. The pool is equipped with Philips Hue lighting to create the right atmosphere at all times and a Bose Soundtouch bluetooth sound system

Rural Tuscany | Farmstay with pool & garden
The Tuscan estate Terra di Cortona lies in a strategic position between the beautiful Tuscan town of Cortona and the Trasimeno lake. The farmhouse consists of five spacious apartments and has a history that goes back to the late 17th century, when a noble family built it as a holiday residence. Air conditioning is available, as well as satellite television and Internet access. In the garden of the property there is a pool with solarium, barbecue and volleyball field.

Borgo La Fonte
❊ Private Outdoor Spaces: private garden with a gazebo adorned with fragrant jasmine, perfect for al fresco dining or relaxing moments ❊ Ease and Convenience: located between Camucia and Cortona, starting point for exploring the region and enjoying a relaxing vacation with all services close at hand ❊ Modern Comforts: fully equipped kitchen, two double bedrooms, and two bathrooms with showers ❊ Private Parking: a rarity in the area, for a more convenient stay

Chicca: Cortona's historic center
Bright, delightful and welcoming apartment located right in the heart of the historic center of Cortona with an unforgettable view: the town hall on one side and Lake Trasimeno and the Valdichiana on the other. The apartment has been recently renovated and consists of a living room with sofa bed, a small kitchen, a double bedroom and two bathrooms. The apartment has WiFi, heating and air conditioning, a washing machine, oven, microwave, hairdryer and flat iron.

Netik Apartment
Welcome to Vallone di Cortona ✨ A peaceful retreat in the heart of Tuscany, where time slows down among the scents and colors of the vineyards 🍇. 🎁 A special gift for you: enjoy a complimentary bottle of our wine 🍷 and our extra virgin olive oil 🫒 upon arrival to start your Tuscan experience. The villa 🏡 combines modern comfort and rural charm, offering stunning views of cypresses 🌲, golden hills 🌻, and breathtaking sunsets 🌅.
Popular amenities for Ossaia vacation rentals
Other great vacation rentals in Ossaia

Fabulous Farmhouse with Pool & 360 Panoramic View

the oasis of the foxes

Villa Chiara

Lake View Private Villa with Pool

La Pergola | Farm House with fantastic view

Hidden gem in Tuscany

Breathtaking views: Historic House w/Terrace & BBQ

Casa Primo Stylish-townhouse w/ patio & jetted tub
Destinations to explore
- Lake Trasimeno
- Lake Bolsena
- Del Chianti
- Basilica of St Francis
- Frasassi Caves
- Centro Storico Orvieto
- Cascate del Mulino
- Mount Amiata
- Furlo Gorge Nature Reserve
- Eremo Di Camaldoli
- La Scarzuola
- Avignonesi Winery Fattoria Le Capezzine
- Antinori nel Chianti Classico
- Siena Cathedral
- Val di Chiana
- Palazzo Pubblico
- Mount Subasio
- Valdichiana Outlet Village
- Terme San Filippo
- Saturnia Thermal Park
- Gola del Furlo
- Abbey of Monte Oliveto Maggiore
- Abbey of Sant'Antimo
- Rocca Maggiore





