
Vacation rentals in Castiglioncello di Trinoro
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Top-rated vacation rentals in Castiglioncello di Trinoro
Guests agree: these stays are highly rated for location, cleanliness, and more.

Charming Tuscan Villa in Val d'Orcia with a view
Luxury and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, commercial kitchen at your own use. We arrange Winery visit & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!
FamilyLocationSleep quality
4.97 out of 5 average rating, 130 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.
FamilyValueCleanliness
4.97 out of 5 average rating, 251 reviews
Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting or barbecue for all the guests of our 4 apartments, after 7pm if booked large in advance Large free parking area 100 mt away
FamilyValueLong stay
4.98 out of 5 average rating, 165 reviews
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.
LocationFamilyView
4.98 out of 5 average rating, 187 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
FamilyLocationAccuracy
4.92 out of 5 average rating, 337 reviews
Your Tuscan oak tree house, enchanting Val d'Orcia
The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.
ValueFamilyBeach
5.0 out of 5 average rating, 116 reviews
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.
ValueFamilyBathroom
4.98 out of 5 average rating, 160 reviews
In Toscana Camere
**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.
LocationValueHospitality
4.96 out of 5 average rating, 137 reviews
Castello di Spedaletto, Val d'Orcia, Pienza
L'agriturismo Castello di Spedaletto sorge nell’edificio che un tempo ospitava il granaio dell’antico castello medioevale ed è stato recentemente ristrutturato in perfetto equilibrio tra modernità e tradizione: pietra, mattoni, travi a vista si fondono con la caratteristica scalinata in cristallo e ferro battuto. L'agriturismo è formato da 5 camere matrimoniali con bagno e 2 appartamenti. Vieni, Vedi, Vivi…
FamilyLocationPets
4.97 out of 5 average rating, 185 reviews
Unique view 3 bdr villa with pool & A/C in Pienza
Nestled within the picturesque Val d'Orcia National Park and the enchanting Natural Reserve of Lucciola Bella, this apartment sits perched on a natural terrace, offering unparalleled views of Mount Amiata. Immerse yourself in the untouched beauty of this protected oasis, where the ever-changing play of sunlight and the rhythm of the seasons paint a constantly shifting panorama across the rolling hillsides.
LocationFamilyBathroom
4.95 out of 5 average rating, 104 reviews
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.
ValueLocationGrill
4.96 out of 5 average rating, 170 reviews
Agriturismo Poggio Bicchieri ap. Poesia
Il nostro agriturismo è una finestra sulla val d'orcia, composto da 2 appartamenti con cucina, camera e bagno. Grande giardino attrezzato. Immerso nel silenzio, vicino a Pienza, Montalcino, Bagno Vignoni e le terme naturali di Bagno San Filippo. Per raggiungerci è molto semplice, l'ultimo km di strada è sterrata ma percorribile da tutti.
FamilyLocationPets
4.95 out of 5 average rating, 579 reviewsPopular amenities for Castiglioncello di Trinoro vacation rentals
Other great vacation rentals in Castiglioncello di Trinoro

L'Aquila e L'Ulivo
LocationFamilyView
5.0 out of 5 average rating, 129 reviews
Alma Vignoni - Vignoni Val d'Orcia - Bagno Vignoni
ValueFamilyAmenities
4.99 out of 5 average rating, 233 reviews
Breeder's Room - Triple room breakfast included
ValueLocationGetting around
5.0 out of 5 average rating, 108 reviews
Villa with private pool, air conditioning, Wi-fi
LocationValueLayout
4.92 out of 5 average rating, 12 reviews
Appartamento Ronda a Chiarentana, Val d'Orcia
FamilyLocationWalkability
4.95 out of 5 average rating, 22 reviews
La Corte del Podestà
ValueLocationComfort
4.96 out of 5 average rating, 26 reviews
Elegant farmhouse overlooking Pienza
LocationFamilyAccuracy
5.0 out of 5 average rating, 36 reviews
Elegant historic Palazzo, views of Tuscan valley
FamilyValueAccess
4.97 out of 5 average rating, 86 reviewsDestinations to explore
- Lake Trasimeno
- Lake Bolsena
- Parco Regionale Della Maremma
- Feniglia
- Lake Vico
- Del Chianti
- Basilica of St Francis
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- Terme Dei Papi
- La Scarzuola
- Villa Lante
- Siena Cathedral
- Vulci
- Avignonesi Winery Fattoria Le Capezzine
- Val di Chiana
- Mount Subasio
- Palazzo Pubblico
- Saturnia Thermal Park
- Valdichiana Outlet Village
- Riserva Naturale Diaccia Botrona
- Terme San Filippo
- Abbey of Sant'Antimo





