
Holiday houses in Toscolano
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Toscolano
Guests agree: these stays are highly rated for location, cleanliness and more.

Beautiful villa in Umbria
Welcome to our beautiful Italian villa designed by a famous Italian stage designer. Unobstructed panoramic views over the Umbrian countryside. Enjoy complete relaxation, privacy and peace with friends and family by the 12 meter pool or underneath the 200 year old oak tree. Large farmhouse style kitchen, herb garden, pizza oven and large garden with olive and fig trees. Located in Toscolano, Umbria with two excellent restaurants and food market - perfect for exploring southern Tuscany and Umbria.

Stylish Umbrian farmhouse in stunning countryside
Welcome to Casale Amerina, an idyllic place to rest, rebalance and revitalise. This is a much-loved Umbrian farmhouse, with stylish contemporary interior, set in wonderful Umbrian countryside. There are two bedrooms with king size beds, a comfy sitting room with a balcony, and a gorgeous kitchen-dining room with Tuscan oak beams and a fireplace. Soak up the sun on our grass lawn, relax in the shade of our olive, walnut and fig trees, or explore the local area with its wonderful hilltop towns.

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.

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

The Cellar (Palazzo Pallotti)
The apartment is two floors below the square, entirely dug into the tuff. Overlooking the valley, it is isolated from the noises of the street, quiet, private, and very welcoming. The tuff walls give it an ancient vibe to transport you to another time. It can be reached on foot, via a footbridge that takes you directly to the square where the property is located. It is perfect for short stays of complete relaxation, but with the fully equipped kitchen you can make the most of it.

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.

Rock suite with hot tub
Leaving the car in the free parking lot, you will have to walk 200 meters to reach this house in the heart of a forest and set in a large rock. All around you can take pleasant walks to the Rio Grande dam. Very suitable for a relaxing weekend in close contact with nature. Suitable for couples (even with pets) who are looking for relaxation, away from the chaos of the cities and who want to escape the responsibilities and stress of life for a while.

The Enchantment of Civita (The Terrace)
L'Incanto di Civita is located inside the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot, you will need to walk along the bridge, the only way to access our "tufo pearl". L'Incanto di Civita is located in the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot you will need to walk along the bridge, the only way to access our "tufo pearl".

Country Chalet and mini spa
A welcoming and comfortable nest, immersed in the bright colors of the Umbrian countryside, among roses and lavender, in the silent garden that frames it... Live a romantic dream: let yourself be enveloped by the warmth of the hot tub, under a starry sky and in the heart of the magic of our chalet. An oasis of tranquility, but well connected to all the major attractions of the region...

Simona’s house in the woods - Villa Boutique
Villa boutique immersa nel bosco all’interno del Parco dei Cimini alle pendici del Monte Cimino (800 m. s.l.m) L'immobile è grande circa 450mq ed è circondato da circa 1,5 ettari di giardino/pineta. La villa è dotata di una sauna e un hot tube a legna privata nel bosco. Una casa progettata da uno dei migliori architetti del centro Italia ed è sapientemente arredata.

House of the Cortese Traveler
The "Casa del Viaggiator Cortese" apartment is located within the medieval village of Toscolano. More precisely, within its original 1400s walls. Staying there gives the guest an experience full of charm. The village of Toscolano is included in the stages of the "Cammino Dei Borghi Silenti" circuit.

San Giusto Abbey {medieval Tower}
Let us tempt you with a truly unique experience: sleeping among the four thick stone walls of a medieval tower! The breathtaking view, the charming and comfortable interiors, sleeping high above, overlooking the world, make staying in the tower absolutely unforgettable.
Popular amenities for Toscolano holiday rentals
Other great holiday rentals in Toscolano

Home in the oak forest - Max. six people

Piazza Marconi Vacation Home

Casa del Castello, charming flat with village view

Fiorire Casale

Casa Amelia Guest House

Linda and Felice Santa Restituta (TR) Rooms for rent

Studio apartment in a 17th-century convent

Apartment in villa and pool 10 minutes from downtown
Destinations to explore
- Lake Trasimeno
- Lake Bracciano
- Lake Bolsena
- Lago del Turano
- Terminillo
- Cascate del Mulino
- Lake Martignano
- Monte Terminilletto
- Lake Vico
- Terme Dei Papi
- Avignonesi Winery Fattoria Le Capezzine
- Basilica of St Francis
- Villa Lante
- Golf Nazionale
- Olgiata Golf Club
- Mount Subasio
- Shopping Mall Porta Di Roma
- Sibillini Mountains National Park
- Farfa Abbey
- Rocca Maggiore
- Saturnia Thermal Park
- Pozzo di San Patrizio
- Monte Terminillo
- Abbey of Sant'Antimo




