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Vacation rentals in Villastrada

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Top-rated vacation rentals in Villastrada

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Guest favorite
A panoramic view of the farmhouse complex reveals multiple stone structures surrounded by lush gardens. Olive and cypress trees line the property, with a swimming pool visible on the left. Vast green fields stretch into the distance, creating a serene countryside landscape.
Apartment in Cantagallina Alta

Il Melocotogno, flat 4 pax in the Trasimeno area!

Between Umbria and Tuscany, near the lakes Trasimeno and Chiusi, lies this beautiful farmhouse. The complex consists of three cottages dating back to the end of last century, carefully restored and cared for in the external and internal finishes. Today 5 apartments are available for rent to guests. Il Melocotogno is an apartment and it can host up to 6 pax with air contitioning. It has a living room with sofa bed, kitchen, two double rooms, bathroom with shower, porch with access to the garden.

4.93 out of 5 average rating, 59 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
Guest favorite
A serene landscape features rolling green hills under a vibrant sunset sky, casting soft colors across the horizon. A stone wall is adorned with lush greenery and flowers, providing a tranquil viewpoint for someone contemplating the picturesque view of the valley and distant hills.
Home in Cetona

Casa Dolce Toscana | Panoramic Suite & View

CASA DOLCE TOSCANA 🖼️ Ciao! Sono Jolanta 😊 Benvenuti nel nostro amato alloggio toscano ,con vista panoramica,immerso nelle colline della Toscana.Un’oasi di pace perfetta per chi desidera rilassarsi e vivere un’esperienza autentica. Situato a pochi chilometri da Siena e Firenze,il nostro alloggio combina il fascino rustico con tutti i comfort moderni. si trova nel cuore del centro storico del famoso borgo di Cetona,sottostante al castello ,con vista sulla valle e il profumo della Toscana.

4.98 out of 5 average rating, 187 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

4.92 out of 5 average rating, 337 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
Guest favorite
A large dining area features a long table surrounded by white chairs, positioned before expansive glass windows. The view reveals a scenic landscape with a swimming pool and rolling hills extending into the distance, framed by wooden beams overhead.
Farm stay in San Fatucchio

2 room apartments in farmhouse whit pool

We have 4 apartments of this type on first floor and on two levels with two bedrooms (one double and a single bedroom. The single bedroom is in the attic and has no door it overlooks the living room), living room with kitchenette, bathroom with shower. The farmhouse enjoys a 360° view of the Umbrian and Tuscan hills and has a garden and shared swimming pool in summer, lounge and playground. This typology can NOT be booked with CHILDREN UNDER 12 or babies and is for max 3 people.

4.9 out of 5 average rating, 261 reviews
Guest favorite
A shaded gazebo features a wooden seating area with white cushions, positioned on a stone patio. The scene captures a serene sunset over the property, with distant views of a saltwater pool and rolling hills, creating a tranquil outdoor setting.
Home in Castiglione del Lago

Spectacular Poolside Sunsets of Tuscan Hill Towns

Enchanting villa with spectacular poolside views of Lago di Chiusi and nearby Tuscan hill towns (Chiusi, Montepulciano). Fall in love with rustic Italy, explore nearby medieval towns, interact with locals, relax by the saltwater pool, enjoy a glass of wine under the gazebo, and listen as the sound of birds and church bells punctuate the peaceful quiet. Experience a “picnicco” at nearby Madrevite winery, offering a fun family-friendly evening of food, wine, & music with locals.

5.0 out of 5 average rating, 6 reviews
Top guest favorite
An aerial view highlights a stone farmhouse nestled within lush greenery, surrounded by mature trees. The structure features a terracotta-tiled roof and a charming porch. A pathway leads to a smaller stone building, providing a sense of harmony with the natural landscape.
Villa in Sarteano

Casale in pietra in Val D’Orcia

Casale toscano del '800 con pietre a vista immerso nella meravigliosa campagna Toscana con uno splendido panorama sulla Val di Chiana. E' circondato da un parco di 6 ettari con un uliveto di 300 piante. Si trova a Sarteano, nel paese, un antico borgo medioevale con un castello da sogno, conosciuto per il Festival della Musica e del Jazz che si svolge alla fine dell'estate. Siamo nella bellissima Val d'Orcia, patrimonio naturale dell'umanità dall'UNESCO dal 2004.

4.98 out of 5 average rating, 160 reviews
Top guest favorite
The image depicts a serene pool area surrounded by lush Mediterranean greenery. A bright orange umbrella provides shade, while a well-maintained stone pathway leads to the entrance of a charming stone farmhouse in the background.
Home in Casalini

Casolare immerso nella natura

"IL PODERACCIO" è un tipico casolare in pietra posto sulle colline che circondano il Lago Trasimeno immerso in una stupenda macchia mediterranea. Il fabbricato si sviluppa su due piani. La piscina ed il giardino fanno da cornice al tutto. Apertura Piscina dal 1 Maggio al 1 5 Ottobre. Si fa presente che in seguito alla emergenza COVID 19 per la pulizia e la sanificazione della casa sono state adottate tutte le direttive previste dalla normativa in merito.

4.99 out of 5 average rating, 111 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, 169 reviews
Top guest favorite
A traditional stone casale is set among lush greenery, featuring wooden shutters on the upper windows. Olive and fruit trees frame the home, enhancing its natural setting. A well-maintained lawn extends around the property, inviting relaxation in this peaceful environment.
Cabin in Cetona

Poggio dell'orso.Traditional Casale. Amazing views

Fantastic, recently restored, 150 years old Casale in Tuscany with amazing views. Two bed rooms, a spacious living room with a double sofa bed, a 85" smart TV, a corner with a desk and a fully equipped kitchen. Outside a stone table, a huge garden, a gazebo, a state of art warmed Jacuzzi (optional if available) a fantastic 6 x 12 infinity pool . All the property is fenced. Pet friendly.

4.96 out of 5 average rating, 170 reviews
Guest favorite
A rustic stone villa is surrounded by lush greenery and tall cypress trees under a clear blue sky. The spacious exterior features multiple arched windows and a welcoming porch, with outdoor seating visible in the front garden.
Villa in Ranciano

Villa A Chiaraluna (Agriturismo)

La grande casa in pietra che si innalza tra le vigne e i cipressi, la sua piscina panoramica, i tessuti colorati e i suoi letti a baldacchino, ti trasporteranno in un’atmosfera pittoresca tra Toscana e Umbria. A soli 5 km dal lago Trasimeno, goditi in famiglia o con gli amici, i grandi spazi che Villa A Chiaraluna mette a tua disposizione.

4.9 out of 5 average rating, 41 reviews

Popular amenities for Villastrada vacation rentals