
Holiday houses in Montalcino
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Top-rated holiday rentals in Montalcino
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Da nonna Ornella - nest in Val d'Orcia
Spectacular views and relaxation guaranteed in this romantic studio in the heart of Val d 'Orcia, province of Siena, immersed in beautiful Tuscany. Ideal for couples. It has a living area, equipped kitchen, bathroom, heating, courtyard, private parking and a large and panoramic garden with sun loungers and hammock. Close to iconic destinations: PIENZA, Montepulciano, Montalcino, Bagno Vignoni, Bagni San Filippo, San Quirico d'Orcia, Radicofani, Castiglione d'Orcia and Monte Amiata. Unforgettable.

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 for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

Montalcino Townhouse with Private Garden & Spa
A luxury apartment that blends traditional elements with all the modern comforts and some contemporary wall art. The apartment is centrally located in the upper part of town, only around the corner from the main square, in the limited traffic area. You can drive close by to download the luggage. The closest free car park is located at less than 10 minutes walk. Please note that to reach the house you need to walk a fairly steep street: it may not be ideal for those with mobility problems.

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.

Bruna's House
LA CASA DI BRUNA A finely renovated apartment, furnished with love and attention to detail, is located inside a historic building The entrance opens onto a living room with a very comfortable sofa connected to a large and comfortable kitchen From the living room, we access the terrace overlooking the fortress where you can enjoy wonderful sunsets On the same floor, there is a bathroom and a bright double bedroom Upstairs is the second bathroom and another comfortable bedroom

Flat, Agriturismo "Biofattoria l'Upupa"
The flat is on the first floor of a classic Tuscan farmhouse called ‘Biofattoria l'Upupa’. Magnificent hillside location between the Val d'Orcia and the Crete Senesi. Suitable for families with children. Consisting of kitchen, large living room, bathroom with shower, 1 double bedroom and 1 bedroom with bunk beds. There is a double sofa bed in the living room. The flat is equipped with wifi. Free parking on private property. Complete breakfast kit including homemade cakes.

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.

"Landscape Notes" Suite
The 80 sqm Suite "Note di paesaggio" is located on the second floor of a historic building where it meets the landscape of the Val d'Orcia. It is divided into several rooms including a furnished double bedroom with air conditioning overlooking the terrace, a living room with a panoramic view, a study with a desk, a marble bathroom with shower, and another double bedroom without air conditioning . You can enjoy a 30sqm terrace and its suggestive view of the countryside.

Apartment in a detached villa - Val d'Orcia
In a cozy independent villa in Tuscan style apartment recently and finely renovated and located in a land rich in history. A few kilometers from the city of art and on Via Francigena, the apartment can be a base for nature or food and wine trails. From a beautiful terrace overlooking the view you can enjoy your meals, admire the sunset and observe the majestic and magnificent medieval Rocca From 22/03/18 municipal tourist tax: €2 per person from 12 years of age

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.

Mascagni Farmhouse in Val d'Orcia, Pienza
Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

House of the Jujube
Facing the old medieval walls of this ancient city, the location of the house will make you feel relaxed thanks to the peacefulness of the countryside and the vitality of the centre. Bathed in the gorgeous sunlight from sunrise to sunset, Casa delle Giuggiole will give you a sensation of lightness and freedom. Look through any one of the many windows and you can admire both the astonishing landscape of the Val d'Orcia and the typical Tuscan roofs.
Popular amenities for Montalcino holiday rentals
Stay near Montalcino's top sights
Other great holiday rentals in Montalcino

Cantagalli Farmhouse, Mugellese Apartment.

Casa Tórta - comfort room

Romantic Tuscan Holiday House

Tuscan villa in the heart of the Val d'Orcia

Podere Ampella House with a Beautiful View

Stunning loft in Montalcino.

Wine House

Casa Francesca
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $181 AUD | $184 AUD | $203 AUD | $213 AUD | $225 AUD | $235 AUD | $237 AUD | $241 AUD | $232 AUD | $219 AUD | $190 AUD | $192 AUD |
| Avg. temp | 8°C | 8°C | 11°C | 13°C | 18°C | 22°C | 25°C | 25°C | 21°C | 17°C | 12°C | 9°C |
Frequently Asked Questions
Are there condo rentals with a dedicated workspace in Montalcino?
Yes! Work meets play with ease at over 30 condo rentals in Montalcino featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in bed and breakfast rentals in Montalcino?
Experience the best of Montalcino with our bed and breakfast rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do bed and breakfast rentals in Montalcino have air conditioning?
Absolutely! We offer over 40 bed and breakfast rentals with air conditioning in Montalcino. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly condo rentals in Montalcino?
Four-legged friends are welcome in Montalcino. Choose from more than 20 condo rentals for guests traveling with pets.
Do villa rentals in Montalcino have wifi?
Absolutely! We offer over 90 villa rentals with wifi in Montalcino. Enjoy a tailored experience with all the comforts you desire.
Are there Montalcino house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 house rentals with pools in Montalcino, available on Airbnb. Make a splash and soak up the sun in style!
Do condo rentals in Montalcino have a kitchen?
Absolutely! We offer over 50 condo rentals with a kitchen in Montalcino. Enjoy a tailored experience with all the comforts you desire.
Do villa rentals in Montalcino have free parking?
Absolutely! We offer over 70 villa rentals with free parking in Montalcino. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly condo rentals in Montalcino?
Montalcino has more than 30 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Farmstay Rentals in Montalcino?
Enhance your stay in our Farmstay Rentals with the most popular amenities: over 60 homes with air conditioning, over 100 homes with a kitchen, over 120 homes with free parking, over 130 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Montalcino

Total holiday rentals
Explore 990 holiday rentals in Montalcino

Nightly prices starting at
Montalcino holiday rentals start at $58 AUD per night before taxes and fees

Verified guest reviews
Over 28,260 verified reviews to help you choose

Family-friendly holiday rentals
530 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 560 rentals that welcome pets

Holiday rentals with a pool
420 properties feature pools

Rentals with dedicated workspaces
390 properties have a dedicated workspace

Wi-Fi availability
930 of Montalcino holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Montalcino rentals

4.8 Average rating
Montalcino stays are highly rated by guests—averaging 4.8 out of 5!
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- Basilica Di San Miniato A Monte
- Lake Trasimeno
- Del Chianti
- Siena Cathedral
- Lake Bolsena
- Feniglia
- Cala Violina
- Gulf of Baratti
- Avignonesi Winery Fattoria Le Capezzine
- Palazzo Pubblico
- Cascate del Mulino
- Santa Maria della Scala
- CavallinoMatto
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Casa Barthel
- Antinori nel Chianti Classico
- Abbazia di San Galgano
- Castello di Verrazzano
- Argentario Golf Resort & Spa
- Mount Amiata
- Val di Chiana
- Riserva Naturale Diaccia Botrona
- San Gimignano 1300
- Things to do Montalcino
- Food and drink Montalcino
- Things to do Siena
- Art and culture Siena
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- Nature and outdoors Siena
- Food and drink Siena
- Things to do Tuscany
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