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Holiday houses in Ossaia

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Top-rated holiday rentals in Ossaia

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Holiday home in Petrignano del Lago
4.98 out of 5 average rating, 124 reviews

Fontarcella, H&R- mediterranean home with jacuzzi

Situata nelle colline a cavallo tra Montepulciano,Castiglione del Lago e Cortona, Fontarcella si presenta come una villetta indipendente immersa nel verde, che offre jacuzzi e parcheggio privati; Scoprirete un luogo senza tempo, per condividere momenti preziosi. La struttura, arredata in stile mediterraneo, dispone di climatizzazione e wi-fi gratuita. Il giardino, interamente recintato, offre vari comfort. A pochi minuti dalle autostrade, Fontarcella è facilmente raggiungibile dai viaggiatori.

Top Guest favourite
A rustic stone building is framed by lush greenery, showcasing wooden shutters and a welcoming arched doorway. A small outdoor table stands nearby, accompanied by planters filled with flowers, all set against a gravel path leading to the home.
Home in Cortona (Pierle)
4.98 out of 5 average rating, 61 reviews

Casetta nel bosco "L'Antico Metato"

Piccolo rudere in pietra ristrutturato all'ombra del bosco, un angolo di paradiso sospeso tra Toscana e Umbria, ideale per rilassarsi e vivere atmosfere del passato. Si trova nei pressi del grazioso Borgo Medievale di Pierle, nel quale domina un castello dell'XI secolo. Anticamente utilizzato come essiccatoio per castagne (metato), il piccolo rudere è stato ristrutturato conservando le caratteristiche originali e con una ispirazione data dalle antiche case coloniche toscane tipiche del luogo.

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 117 reviews

Palazzo Monaci - Piscina nelle crete Senesi

Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

Top Guest favourite
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
4.97 out of 5 average rating, 207 reviews

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.

Superhost
Farm stay in Lisciano Niccone
5 out of 5 average rating, 6 reviews

Pugnano Alto -appartamento Castagna

The holiday apartment "Pugnano Alto - Castagna" is located in Lisciano Niccone and is perfect for an unforgettable holiday with your loved ones. The 75 m² apartment is situated on the first floor of the property and consists of a well-equipped and functional kitchen with a view of the valley, 2 bedrooms with double beds, and 2 bathrooms (each bedroom has its own private bathroom with shower). Additional amenities include Wi-Fi, TV, air conditioning, and a washing machine in the laundry area.

Top Guest favourite
A rustic bedroom features exposed stone walls and wooden beams. A spacious bed is positioned centrally, surrounded by soft linens. A wooden wardrobe and a small side table complement the space, while a vintage chair adds comfort. Natural light filters through the window, illuminating the room.
Home in Tuoro sul Trasimeno
5 out of 5 average rating, 75 reviews

l'oasi delle volpi

Benvenuti al nostro casale del XVIII secolo, un'oasi sulle colline umbre. Ciò che rende il nostro alloggio davvero speciale è la vista mozzafiato sul lago. Ogni dettaglio è stato curato con attenzione, mentre gli elementi originali della casa sono stati restaurati per preservarne l'autenticità. Circondati dalla natura, potrete godervi momenti di tranquillità e serenità. Venite a scoprire questo luogo, dove l'autenticità e la cura dei particolari si fondono per regalarvi un'esperienza unica.

Top Guest favourite
A medieval stone tower stands tall against a clear blue sky, showcasing its historic architecture. The narrow road lined with greenery leads to the entrance, with the texture of the stonework and windows highlighted, inviting guests to explore its unique charm.
Tower in San Quirico d'Orcia
5 out of 5 average rating, 103 reviews

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Guest favourite
A private pool is set against a backdrop of lush gardens and a charming villa. The clear water of the pool reflects the blue sky, and sun loungers are positioned nearby for relaxation. Olive trees dot the landscape, enhancing the tranquil atmosphere.
Home in Cortona
4.91 out of 5 average rating, 23 reviews

Villa Bellora | Tuscan Villa w/ Pool Near Cortona

Villa Bellora: Your Tuscan Summer Escape Book now for summer stays and enjoy golden sunsets, blooming sunflower fields, a private pool, and peaceful countryside charm. This 3-bedroom, 2-bath villa near Cortona and Montepulciano offers lush gardens, cozy living spaces, a fully equipped kitchen, and outdoor dining. Relax by the pool, explore hilltop towns, or unwind under the stars—your perfect Tuscan getaway awaits.

Top Guest favourite
Villa in Castel Rigone
5 out of 5 average rating, 22 reviews

Villa Feronia – Heated Pool & Rooftop Escape

Welcome to Villa Feronia, a contemporary 3-bedroom retreat nestled in a 2-hectare olive grove near Passignano sul Trasimeno. Enjoy refined indoor-outdoor living with 3.5 bathrooms, high-speed Wi-Fi, a smart home system, an infinity saltwater heated pool, and a rooftop terrace with a fire pit. Eco-friendly and elegantly designed, it’s the ideal escape to relax, recharge, and experience authentic Italian beauty.

Top Guest favourite
A serene bedroom space features a spacious bed adorned with soft, neutral-toned linens. Sheer white drapes create a cozy atmosphere, while the open doors offer a view of the lush outdoors, inviting natural light into the room.
Farm stay in Arezzo
4.98 out of 5 average rating, 244 reviews

Esplora la natura al centro di Vigneti Chianti

Feel close to the land in a rustic building on a Tuscan farm. Old stone walls, ceilings with exposed beams and terracotta floors are the backdrop to a characteristic apartment with fireplace. Plunge into an infinity pool for a unique view of the surrounding landscape. Dine outdoors, with the fresh air caressing you, sit and relax admiring the sunset under the ancient cypresses.

Guest favourite
A spacious bedroom is showcased with a romantic canopy bed complemented by soft linens. The wood-beamed ceiling adds character, while a vintage armchair and a wardrobe provide functional elegance. Soft lighting creates a calm ambiance in the inviting room.
Home in Greve in Chianti
5 out of 5 average rating, 20 reviews

La Terrazza sul Borgo - Montefioralle Apartment

L'appartamento "La terrazza sul Borgo" nasce all'interno di uno storico edificio nello stupendo borgo medievale di Montefioralle, uno dei borghi più belli d'Italia. La struttura, risalente a circa 1000 anni fa, è stata completamente ristrutturata nel Gennaio 2020 cercando di preservare tutte le caratteristiche originali che ne fanno un ambiente unico.

Top Guest favourite
A serene outdoor space is framed by tall, leafy trees, creating a natural canopy. Within the gravel area, terracotta pots with greenery are visible, offering a sense of tranquility. The expansive view stretches across the hills and valleys of the surrounding landscape.
Apartment in Cortona
4.96 out of 5 average rating, 177 reviews

Casa Le Contesse

È un piccolo appartamento, porzione della casa colonica dove vivo. È situato a piano terra, con accesso indipendente, in collina, in mezzo agli olivi, ad un km da Cortona. C'è possibilità di parcheggio, accesso privato, usufruire del giardino "superpanoramico''

Popular amenities for Ossaia holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Arezzo
  5. Ossaia