Vacation rentals in Ossaia

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

Lake View Private Villa with Pool

Independent private-use stone villa with pool, al fresco living & lush gardens, enjoys stunning views over enchanting Lake Trasimeno. Air-conditioning in bedrooms from 2027***(surcharge). Immersed in beauty & tranquillity by a hillside nature reserve, with driving proximity to the lakeshore, medieval villages, local shops & restaurants. An ideal sanctuary for blissful R&R, (or smart working) in complete privacy, and exploring Umbria-Tuscany natural and historic heritage, and food & wine culture.

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.

Breathtaking views: Historic House w/Terrace & BBQ

Welcome to our longtime family home — an elegant, light-filled space in the heart of Cortona. Set in a quiet historical square just steps from the main piazza. Enjoy spectacular views of the valley, lake and city. This elegant house blends the character of Tuscany with warmth and comfort. Antique terracotta beamed ceilings floors, a terrace with panoramic views, a house that tells a story. It's a space for travelers who appreciate beauty, quiet, and the atmosphere of an authentic home.

Fabulous Farmhouse with Pool & 360 Panoramic View

In the very centre of Italy, straddling the border of Umbria and Tuscany, this carefully restored farmhouse makes a great base for a memorable Italian holiday. Situated in an idyllic hillside position overlooking Montepulciano, ‘La Colomba’ is blessed with 360-degree views of iconic Italian landscape and fully equipped with all child amenities. Within easy reach of many of the world’s most important historical and cultural attractions, this house really is The Italian Dream.

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.

the oasis of the foxes

Welcome to our 18th-century farmhouse, an oasis in the Umbrian hills. What makes our accommodation really special is the breathtaking lake view. Every detail has been taken care of, while the original elements of the house have been restored to preserve their authenticity. Surrounded by nature, you can enjoy moments of tranquility and serenity. Come and discover this place, where authenticity and attention to detail come together to give you a unique experience.

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 🌅.