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Holiday rentals in Montecastelli

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Top-rated holiday rentals in Montecastelli

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Top guest favourite
The image shows a historic villa with a stone façade and a prominent tower. The property is surrounded by a well-kept lawn, with a clear pathway leading to the entrance. Lush greenery and decorative planters enhance the inviting appearance of the building.
Villa
5 out of 5 average rating, 103 reviews

Torre Villa Belvedere Luxury & Relax with pool

"TORRE VILLA BELVEDERE" Meraviglioso appartamento di 260 metri quadrati , in Villa del XII sec .La piscina privata ( lunga 15 metri e larga 5 metri ) ,biliardo, biliardino, freccette,ampio giardino , portico 80 mq, barbecue,palestra e area relax all'interno della Torre. Comodo parcheggio privato all'interno della struttura. Situato in posizione strategica ,12 Km da Perugia, 4km dalla superstrada,può ospitare comodamente fino a 8 ospiti 3 camere matrimoniali con bagno privato, Tv, cassaforte

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.
Guest house
4.97 out of 5 average rating, 209 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.

Top guest favourite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay
4.99 out of 5 average rating, 474 reviews

Agriturismo Fattoria La Parita

Appartamento in stile provenzale immerso tra il vigneto e gli olivi. Godrete della tranquillità della campagna a 10 km dalla città e 4 dall'autostrada. Il canto di ghiandaie e cucù faranno da colonna sonora al soggiorno mentre i caprioli brucano tra gli olivi. E' inclusa una colazione base all'italiana (caffè, tè, latte, biscotti ecc.), se invece preferite una colazione più ricca e servita al tavolo il costo è 15€ a persona (10€ da 5 a 15 anni, gratis meno di 5 anni). Disponibile wallbox EV.

Top guest favourite
A rustic stone farmhouse is nestled in a lush green landscape, surrounded by rolling hills and tall cypress trees. The sun casts a warm glow on the exterior, highlighting the charming architecture. An open courtyard with a small pool can be seen in the foreground.
Farm stay
4.91 out of 5 average rating, 561 reviews

Agriturismo Poggio Bicchieri ap. Memoria

Rilassati con tutta la famiglia in questo alloggio. L’agriturismo si compone di due appartamenti indipendenti con sala, cucina, camera e bagno. Non dovrai condividere nulla con il altri ospiti poiché é stata nostra cura organizzare tutto in maniera che ognuno abbia i propri spazi e tutto sia separato. All'esterno c’é un barbecue, tavolo con sedie e le sdraio. Nelle vicinanze Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino e Bagni San Filippo. Per raggiungerci 1,5 km di strada sterrata!

Guest favourite
The villa is surrounded by lush greenery, showcasing an inviting infinity pool that reflects the sky. The stone exterior of the house features warm wooden shutters, with outdoor seating visible on the terrace. Nearby, lavender plants create a serene ambiance against the landscape.
Villa
4.88 out of 5 average rating, 50 reviews

Villa San Martino, on the Tuscany/ Umbria border

Villa San Martino is not just another holiday in Tuscany or Umbria - this is a really special place. With spectacular views across the world famous Niccone Valley towards Mercatale di Cortona, relax in the infinity pool, or dine alfresco on the terrace. From the villa you can easily access the enchanting towns of Cortona, Pienza, Montepulciano, Siena, Perugia, Assisi and Florence. The Niccone valley is home to delightful restaurants and you can sample great local Tuscan & Umbrian cuisine.

Guest favourite
A saltwater pool is framed by lush greenery, with sun loungers placed beside it. The setting features rolling hills in the background under a partly cloudy sky, creating a serene atmosphere. Stone walls surround the pool area, enhancing the natural beauty of the location.
Villa
4.91 out of 5 average rating, 33 reviews

Fattoriafontenovo, country house Perugia, Umbria

Welcome to our charming apartment in Fattoria Fontenovo in Umbria fresh hills !This cozy retreat at our historic Fontenovo Farm, owned by our family for over 100 years, offers the perfect blend of privacy and tranquility. Some areas of the spacious villa remain unoccupied and others are reserved for your use. During the stay, you'll be the sole occupants, apart from the owners who may occasionally be in another part of the house. Enjoy the lush gardens, private pool, and serene countryside.

Guest favourite
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
4.92 out of 5 average rating, 285 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

Top guest favourite
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
4.99 out of 5 average rating, 137 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.

Top guest favourite
A rustic living area features a wooden table surrounded by two elegant armchairs and a beige sofa. A stone fireplace, stocked with logs, stands as a focal point, while wooden beams adorn the ceiling. An inviting atmosphere is created by warm, natural colors and soft furnishings.
Home
4.99 out of 5 average rating, 258 reviews

Casa Rosmarino Eco-Wellness Country Home

Summer 2026 villas w/private pool available : airbnb.com/h/casaflavia10 airbnb.com/h/villaflaviaarezzo Price includes: - Infrared Sauna - Wood for Fireplace - Fire starters - Heating/Air Conditioning - Laundry/Dryer - Shower Gel/Shampoo/Bathrobes - Welcome Appetizer w/Wine - Treats during your stay Pool & parking lot are shared areas. We have 6 units for rent Extra activities (not included) : - Massages, Cooking Classes, Tours & Tasting Please INQUIRE for price & availability.

Guest favourite
A private swimming pool is surrounded by lush greenery, with a smooth stone wall bordering the area. Wooden lounge chairs are positioned nearby, offering shaded comfort under a wooden pergola. The turquoise water reflects the sky, creating a serene outdoor space.
Home
4.98 out of 5 average rating, 58 reviews

Landhaus mit Pool in Nord-Umbrien Grenze Toskana

Wir vermieten unser wunderschönes, restauriertes Haus. Es liegt in absoluter Alleinlage im Wald mit einer traumhaften Aussicht. Wir haben einen riesiges Grundstück und Garten mit einem Pool zur privaten Nutzung. WLAN im gesamten Haus und am Pool. Wir sind 20 km von der Grenze zur Toskana entfernt, daher eignet sich unser Haus perfekt als Ausgangsort für Ausflüge in die Toskana, wie auch nach Umbrien. Pool geöffnet von Mitte Mai bis Ende September - Änderungen sind möglich

Top guest favourite
The farmhouse entrance is framed by two potted plants and orange pumpkins. A stone facade features a wooden door with gray shutters, complemented by a tiled roof. Natural surroundings are visible in the background, emphasizing the peaceful rural setting.
Home
4.98 out of 5 average rating, 140 reviews

Tofanello Orange Luxury and Modern Comfort with Outdoor Pool

Escape to the rolling hills of Umbria in this updated farmhouse (90 m2 over 2 floors) that retains its original charm. The home features classic beamed vaulted ceilings, original stone finishes, an indoor wood-burning fireplace, private entrance and a private garden terrace. The shared pool has a large sun lounge area. If your favourite dates aren't available anymore take a look at our turquoise apartment. Turquoise: https://www.airbnb.com/rooms/plus/9430389.

Top guest favourite
A rustic stone farmhouse is embraced by mature olive trees and lush greenery. The building features traditional window shutters and is set against a clear blue sky, with a gravel pathway leading up to the entrance, enhancing the tranquil countryside ambiance.
Farm stay
4.99 out of 5 average rating, 104 reviews

Podere Pereti Nuovi-modern Tuscan Villa

Podere I Pereti was entirely build by our grandfather Remo in the 1970's. My siblings and I spent most of our summers on the porch with our grandparents watching sunsets and admiring the view of the Val d'Orcia. Entirely surrounded by vineyards and olive groves. Nonno Remo, besides having a building company, proudly produced Orcia red wine that was consumed by the family. From the 150 olive trees, every November we filled our tanks with green gold olive oil.

Popular amenities for Montecastelli holiday rentals

  1. Airbnb
  2. Italy
  3. Umbria
  4. Perugia
  5. Montecastelli