
Holiday houses in Montalcino
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Top-rated holiday rentals in Montalcino
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Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

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.

City Center Palazzo: 4 King BR 6 Bath and Garage
Experience this newly restored historic home in the center of Montalcino, built for one of the most influential families in Montalcino, complete with modern amenities. Imagine having dinner in the restored wine cellar or relaxing in bed as you look up at beautiful frescos on the ceiling. This 4 bedroom home complete with a large living room, dining room/kitchen, and wine cellar dining room is updated with the latest amenities, appliances, high-speed internet, and comfortable lush bedding.

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

"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.

Cappella - farmhouse surrounded by vineyards
L’appartamento Cappella fa parte dell'agriturismo Le Chiuse, una struttura del 1840 immersa nelle vigne. E' ricavato da una piccola chiesetta sconsacrata, composto da un salotto con angolo cottura, poltrone e caminetto, un’ampia camera da letto matrimoniale, un bagno con box doccia, uno stanzino ed un soppalco con un letto matrimoniale. Dotato di aria condizionata. La finestra della camera da letto principale è dotata di zanzariera. Apertura piscina Giugno-Ottobre

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.

La Casetta di Brunello, very panoramic with terrace
STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.
Popular amenities for Montalcino holiday rentals
Stay near Montalcino's top sights
Other great holiday rentals in Montalcino

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Montalcino Loft

NEW Panoramic loft with garden in Montalcino

Montalcino Townhouse with Private Garden & Spa
When is the best time to visit Montalcino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $253 NZD | $238 NZD | $246 NZD | $246 NZD | $259 NZD | $271 NZD | $273 NZD | $278 NZD | $268 NZD | $254 NZD | $256 NZD | $256 NZD |
| 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
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 $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Montalcino?
Yes! Work meets play with ease at over 400 vacation rentals in Montalcino featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Montalcino?
Four-legged friends are welcome in Montalcino. Choose from more than 550 vacation rentals for guests traveling with pets.
Are there Montalcino vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 400 vacation homes with pools in Montalcino, available on Airbnb. Make a splash and soak up the sun in style!
Do farmstay rentals in Montalcino have air conditioning?
Absolutely! We offer over 70 farmstay rentals with air conditioning in Montalcino. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Montalcino have a kitchen?
Absolutely! We offer over 60 condo rentals with a kitchen in Montalcino. Enjoy a tailored experience with all the comforts you desire.
Do hotel rentals in Montalcino have wifi?
Absolutely! We offer over 10 hotel rentals with wifi in Montalcino. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Montalcino have free parking?
Absolutely! We offer over 260 apartment rentals with free parking in Montalcino. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Montalcino?
Montalcino has more than 490 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Villa Rentals in Montalcino?
Enhance your stay in our Villa Rentals with the most popular amenities: over 70 homes with free parking, over 80 homes with wifi, over 80 homes with a kitchen, over 60 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Montalcino

Total holiday rentals
Explore 970 holiday rentals in Montalcino

Nightly prices starting at
Montalcino holiday rentals start at $84 NZD per night before taxes and fees

Verified guest reviews
Over 28,460 verified reviews to help you choose

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

Pet-friendly accommodation
Find 550 rentals that welcome pets

Holiday rentals with a pool
400 properties feature pools

Rentals with dedicated workspaces
400 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wifi 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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- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Feniglia
- Del Chianti
- Centro Storico Orvieto
- Gulf of Baratti
- La Scarzuola
- Cascate del Mulino
- Siena Cathedral
- Parco Regionale Della Maremma
- Palazzo Pubblico
- CavallinoMatto
- Antinori nel Chianti Classico
- Valdichiana Outlet Village
- Ugolino Golf Club
- Casa Vasari
- Santa Maria della Scala
- Terme San Filippo
- Mount Amiata
- Saturnia Thermal Park
- Abbey of Sant'Antimo
- Basilica Di San Miniato A Monte
- Abbey of Monte Oliveto Maggiore
- Things to do Montalcino
- Food and drink Montalcino
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- Food and drink Siena
- Things to do Tuscany
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