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Vacation rentals in Ossaia

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Top-rated vacation rentals in Ossaia

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A bright dining area is illuminated by large windows, revealing scenic views of the surrounding landscape. A rustic wooden table is set with dinnerware and surrounded by benches. Potted plants adorn the window sills, enhancing the natural ambiance of the space.
Villa in Ossaia
4.75 out of 5 average rating, 20 reviews

Casa Lamate

In a beautiful panoramic position overlooking the Valdichiana, Casa Lamate is a splendid farmhouse characterized by the architectural peculiarities of the Tuscan style such as a loggia, terracotta floors and wooden beams. The house is spread across three floors, each with direct access from the outside. The main entrance opens onto the spacious, fully equipped kitchen and adjacent outdoor veranda, ideal for enjoying excellent dinners while enjoying the view. An arch separates the dining area from the cozy living room with sofas and a typical stone fireplace. On the first floor is the sleeping area consisting of three bedrooms. One double bedroom has an ensuite bathroom with shower; two other bedrooms (one double and one with a French bed and a single bed on the lovely mezzanine) share a bathroom with shower. On the lower floor, there is the fourth bedroom consisting of a double bed and a single bed; a bathroom with shower; a small "gym corner" with treadmill and exercise bike and the laundry room. Outside, the 1,500 m2 of terraced and fully fenced garden surrounding the house are the ideal place to spend pleasant moments relaxing in the shade of the olive trees and oaks that adorn the lawn. A small corner is dedicated to the barbecue area and wood-burning oven. A characteristic stone staircase leads into the beautiful pool area equipped with sun loungers, deckchairs and parasols. Adjacent to the pool is a small annex with a kitchenette and a bathroom with a shower. Casa Lamate is a few kilometers from the renowned Etruscan town of Cortona, rich in traditions, culture, art and gastronomy. The strategic location makes it an ideal starting point to visit the major centers of historical-cultural and landscape interest in Central Italy.

Top guest favorite
The exterior of the house is depicted, featuring a two-story structure with a light yellow facade and brown shutters. Lush greenery surrounds the building, including tall trees and flowering plants. A pathway leads to the home against a backdrop of a blue sky with scattered clouds.
Home in Cortona
4.95 out of 5 average rating, 108 reviews

Casa Lucy

House located on the Cortonese hill, completely renovated, consisting of 3 double bedrooms, 2 bathrooms and an open space kitchen and dining room. It is located 5 minutes from the historic center of Cortona and in an excellent position to reach the most beautiful and characteristic places of Tuscany and Umbria such as Pienza, Montepulciano, Castiglione del Lago up to cities that are cradles of art such as Florence, Arezzo, Siena and Perugia. Mandatory tourist tax to be paid on site (€2.50 per person for 4 days)

Top guest favorite
The exterior of the accommodation features a charming white facade with green shutters. A table with chairs is set under a large umbrella, surrounded by blooming red flowers. The entrance showcases wooden double doors, adding to the inviting atmosphere.
Home in Casorbica-Salcotto
4.95 out of 5 average rating, 64 reviews

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.

Guest favorite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino
4.9 out of 5 average rating, 240 reviews

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

Guest favorite
A shaded outdoor seating area features a white sofa and black wicker chairs, facing a view of Lake Trasimeno. A small table holds drinks, while vibrant sunflowers are arranged nearby. The pool is visible in the background, surrounded by lush greenery.
Villa in La Cima
4.92 out of 5 average rating, 50 reviews

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.

Top guest favorite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.92 out of 5 average rating, 332 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Guest favorite
Aerial view of a scenic agriturismo surrounded by vineyards and rolling hills. The property features a pool and is framed by tall cypress trees, enhancing the natural landscape of lush green and golden fields under a partly cloudy sky.
Farm stay in Montepulciano
4.96 out of 5 average rating, 115 reviews

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.

Top guest favorite
An infinity pool is framed by stone decking and wooden lounge chairs, inviting relaxation. Umbrellas provide shade, while terraced gardens with olive trees rise in the background. The surrounding landscape features gently rolling hills and clear blue skies, enhancing the serene outdoor setting.
Villa in Cortona
5.0 out of 5 average rating, 96 reviews

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.

Guest favorite
The pool area features a rectangular swimming pool surrounded by meticulously landscaped gardens. Olive trees, rosemary, and rose bushes complement the scenic views of rolling hills and distant mountains under a clear blue sky.
Villa in Pozzuolo
4.92 out of 5 average rating, 60 reviews

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.

Top guest favorite
Vacation home in Tuoro sul Trasimeno
5.0 out of 5 average rating, 97 reviews

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.

Guest favorite
Villa in Vallone Pip
4.92 out of 5 average rating, 24 reviews

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 🌅.

Top guest favorite
An aerial view showcases the expansive grounds of Villa Pergo, surrounded by lush greenery and fields. The infinity pool is highlighted, surrounded by sunbeds and shaded by cypress and ancient trees. The countryside landscape stretches into the distance, enhancing the villa's serene setting.
Villa in Pergaccio
5.0 out of 5 average rating, 65 reviews

Villa Pergo is an ancient charming country villa

Stay in a piece of Tuscan history at Villa Pergo, a charming countryside estate dating back to 1640. Surrounded by olive groves and rolling hills near Cortona, the villa offers authentic character, panoramic views, and a beautiful infinity pool. With space for up to 11+1 guests in 6 bedrooms, large gardens and peaceful surroundings, it is the perfect retreat for families or groups looking to experience the true charm of Tuscany.

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