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Vacation rentals in Montecastelli

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Montecastelli

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

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Top guest favorite
Villa in Chianciano Terme
4.97 out of 5 average rating, 126 reviews

Villa with View for Family & Friends, in Tuscany

Huge 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, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

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
4.97 out of 5 average rating, 230 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 favorite
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 in Ruscello
4.99 out of 5 average rating, 509 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.

Guest favorite
The image features a contemporary house positioned near a serene lake, surrounded by lush greenery. The building's large windows reflect beautifully on the water's surface, while tall trees frame the scene, creating a peaceful atmosphere in nature.
Cottage in Gubbio
4.95 out of 5 average rating, 20 reviews

Casa sul lago Sorgenti nel bosco

Casa in riva al lago in un ambiente unico e suggestivo a stretto contatto con la natura ed il verde circostante. Nuova costruzione con tutti i confront per garantire un soggiorno da fiaba. La location è appartata e tranquilla, trasmette relax e pace anche se a solo 1 km dalla statale per Gubbio. La cucina ben attrezzata per poter cucinare e mangiare vista lago in un ambiente curato nei dettagli. Sara' la cornice per una vacanza indimenticabile. I cani sono i benvenuti e soggiornano Gratis.

Guest favorite
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 in Perugia
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.

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
4.93 out of 5 average rating, 312 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

Guest favorite
Villa in Umbertide
5 out of 5 average rating, 20 reviews

Stunning house with pool, final summer discounts

40 mins from Perugia airport and Terontola railway station Charming and tastefully restored farmhouse with panoramic views. Large heated private swimming pool. Outdoor terraces with pergolas for shade. BBQ and pizza oven Security gate and cameras Four bedrooms with air-conditioning, three bathrooms. Two sitting rooms. Full equipped kitchen. Parking up to four cars. Wi-fi throughout. Weekly cleaning included. Washing Machine and Dishwasher Table tennis, Sky TV, indoor and outdoor games.

Top 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
4.99 out of 5 average rating, 166 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 favorite
A historic stone building rises against a clear blue sky, surrounded by olive trees. The inviting pool stretches alongside the structure, enhanced by a smooth stone edge, creating a serene outdoor space for relaxation.
Apartment in Montone
4.98 out of 5 average rating, 45 reviews

Dependance nel castello del Cardaneto

Monolocale nel Castello del Cardaneto (VIII sec) con piscina, parcheggio privato e 4000 mq di giardino. A 2 km da uno dei borghi più belli d’Italia , Montone, famoso per le attrazioni turistiche ed eventi che ne rendono un posto unico. Il monolocale di circa 50mq ha ingresso indipendente con affaccio sul giardino, ingresso salotto camera matrimoniale e bagno. Piscina panoramica con vista su Montone per tutti gli odpiti. Disponibile altro appartamento con cucina e balcone privato.

Top guest favorite
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 in Prato
4.98 out of 5 average rating, 143 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 favorite
Apartment in Umbertide
5 out of 5 average rating, 18 reviews

B&B Lavinia

Nel cuore del centro storico di Umbertide, B&B Lavinia, offre un accogliente appartamento, con comodo accesso a piano terra, ristrutturato e curato nei minimi dettagli composto da una spaziosa camera matrimoniale, bagno con doccia e bidet, ampia zona living con divano letto e cucina. La location è strategica oltre che per visitare la caratteristica cittadina, anche per raggiungere facilmente i luoghi più famosi della regione come Perugia, Assisi e Gubbio.

Top guest favorite
An outdoor dining area is set under a wooden pergola, featuring a large wooden table surrounded by chairs. View of lush greenery and rolling hills is visible in the background. Wine bottles and glassware are arranged on the table, ready for a meal.
Guesthouse in Molino Vitelli
4.99 out of 5 average rating, 87 reviews

L'essiccatoio

The house is in a good location for country walks, wildlife, sun, and sightseeing. It's in a nature filled valley with easy routes to interesting places like Siena or smaller towns such as Montone. The house is desirable because of the location, the people, the ambiance, the outdoors space, and the neighborhood. This small place is good for couples and solo adventurers. Wi-fi access has recently been improved in the house.

Popular amenities for Montecastelli vacation rentals

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