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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

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.

4.75 out of 5 average rating, 20 reviews
Top guest favorite
A spacious exterior view reveals a charming stone house complemented by vibrant sunset lighting. The image showcases an inviting outdoor seating area with two chairs, set against a backdrop of lush hills and the distant glimmer of the lake.
Home in Perugia

La Perla del Lago Holiday home on Lake Trasimeno

La Perla del Lago: your refuge at Trasimeno ​Rediscover your harmony in this oasis of absolute peace. Let yourself be enchanted by our magical view and the sunsets that the lake offers every evening. The La Perla del Lago Vacation Home overlooks the mirror of Lake Trasimeno. 8 minutes away you will find the highway to visit towns such as Florence, Perugia, Gubbio, Spoleto, Norcia and many others. In the village, you will find cafés, restaurants, a market, a pharmacy, ATMs, and children's play areas; 3 km away, there is a beautiful swimming pool for summer relaxation.

4.98 out of 5 average rating, 207 reviews
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

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

4.9 out of 5 average rating, 240 reviews
Top guest favorite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

4.97 out of 5 average rating, 251 reviews
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

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

4.93 out of 5 average rating, 336 reviews
Guest favorite
Aerial view of a serene agriturismo surrounded by lush vineyards and golden fields. The property features a pool set amidst well-kept gardens and tall cypress trees. Rolling hills in the background extend towards the horizon, contributing to the peaceful landscape.
Farm stay in Montepulciano

Tuscan farmhouse stay with restaurant and pool

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.

4.94 out of 5 average rating, 108 reviews
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

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.

5.0 out of 5 average rating, 96 reviews
Guest favorite
Home in Cortona

[Antico Casale]Tuscan Views & Private Pool Cortona

Entire farmhouse finely restored to bring back the authentic spirit of a historic stone farmhouse in Cortona. ✔ Suitable for up to 12 guests ✔ Private swimming pool ✔ 1 km from the center of Cortona ✔ Property composed of the main farmhouse on two levels (ground floor and first floor) plus a separate dependance ✔ 3 double bedrooms, 2 twin bedrooms, 1 sofa bed ✔ 3 fully equipped kitchens, 3 full bathrooms, private parking ✔ Outdoor space with a unique view and dining tables

4.94 out of 5 average rating, 34 reviews
Top guest favorite
Vacation home in Tuoro sul Trasimeno

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.

5.0 out of 5 average rating, 97 reviews
Top guest favorite
A light-filled living space features a comfortable sofa and a dining table set for four. A large TV is mounted on a white cabinet, while a door leads to the bedroom area, which appears partially visible in the background. Wooden beams enhance the ceiling's charm.
Condo in Cortona

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.

4.98 out of 5 average rating, 224 reviews
Top guest favorite
Vacation home in Petrignano

Fontarcella, H&R- mediterranean home with jacuzzi

Located in the hills between Montepulciano, Castiglione del Lago, and Cortona, Fontarcella is a detached villa surrounded by greenery, offering a private jacuzzi and parking. You'll discover a timeless place to share precious moments. The property, furnished in Mediterranean style, features air conditioning and free Wi-Fi. The fully fenced garden offers a variety of amenities. Just minutes from the highways, Fontarcella is easily accessible for travelers.

4.98 out of 5 average rating, 168 reviews
Guest favorite
Villa in Vallone Pip

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 🌅.

4.92 out of 5 average rating, 25 reviews

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