
Holiday houses in Montalcino
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Quick stats about holiday rentals in Montalcino

Total holiday rentals
Explore 120 holiday rentals in Montalcino

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

Verified guest reviews
Over 3,160 verified reviews to help you choose

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

Pet-friendly accommodation
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
120 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!
Top-rated holiday rentals in Montalcino
Guests agree: these stays are highly rated for location, cleanliness and more.

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.
ValueFamilyGetting around
4.96 out of 5 average rating, 142 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.
LocationValueAccess
4.97 out of 5 average rating, 251 reviews
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
LocationFamilyCheckout
4.98 out of 5 average rating, 165 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
ValueLocationAccess
4.93 out of 5 average rating, 335 reviews
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.
LocationFamilyBathroom
5.0 out of 5 average rating, 116 reviews
"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.
ValueFamilyWalkability
4.95 out of 5 average rating, 144 reviews
Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni
Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.
LocationValueSolo travel
4.99 out of 5 average rating, 233 reviews
In Tuscany Rooms
**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.
LocationFamilyNearby
4.96 out of 5 average rating, 137 reviews
La Casetta di Brunello, very panoramic with terrace
WE'RE WORKING FOR YOU. ... 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.
FamilyValueView
4.9 out of 5 average rating, 324 reviews
Panoramic nest in Montalcino
A completely independent accommodation recently refurbished - from the design to the furnishings - directly by the host. It is composed of a living room with a fully equipped kitchen and a bedroom with bathroom. The peculiarity of the property is the extremely favorable location in the historic center, with a splendid terrace with panoramic garden on the Val d'Orcia, with barbecue, hammock, sink and outdoor shower.
LocationValueAir conditioning
4.98 out of 5 average rating, 163 reviews
Castel Brunello - 2 doublebed rooms + terrace
Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.
ValueLocationIndoor spaces
4.99 out of 5 average rating, 118 reviews
Poggio Bicchieri Holiday Farm - Poesia apartment
Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.
FamilyLocationTV
4.95 out of 5 average rating, 579 reviewsPopular amenities for Montalcino holiday rentals
Other great holiday rentals in Montalcino

Podere Pereti Nuovi – Modern Tuscan Villa
LocationValueHospitality
4.98 out of 5 average rating, 116 reviews
Casa Dolce Toscana | Panoramic Suite with View
FamilyLocationParking
4.98 out of 5 average rating, 186 reviews
Mimosa Apartment - Poggio al Vento
LocationFamilyBreakfast
4.99 out of 5 average rating, 112 reviews
Unique views from inside Montalcino
LocationFamilyCheckout
4.91 out of 5 average rating, 70 reviews
Stunning loft in Montalcino.
LocationFamilyView
4.95 out of 5 average rating, 20 reviews
Podere Belsogno
ValueLocationLaundry
4.93 out of 5 average rating, 89 reviews
Tuscan Farmhouse ~ Magic Sunsets ~ 360° view
ValueLocationAccuracy
4.98 out of 5 average rating, 46 reviews
Montalcino Vacation Home Idolina Guest House
FamilyValueDecor
4.97 out of 5 average rating, 29 reviewsWhen is the best time to visit Montalcino?
| Month | June |
|---|---|
| Avg. price | $254 AUD |
| Avg. temp | 22°C |
Frequently Asked Questions
What are the best places to stay in Montalcino?
Stays near the medieval town center are frequently chosen for walkable access to shops, cafes, and historic sites. For a quieter escape, countryside villas and rural estates around Montalcino immerse guests in scenic vineyards and olive groves.
What are the best things to do in Montalcino with kids?
Families often explore the medieval Fortress of Montalcino, wander local markets, and visit interactive museums around town. Outdoor picnics and guided nature walks in the Tuscan countryside are frequently suggested activities.
What are some of the best things to do in Montalcino?
Explore the Fortress of Montalcino, sample Brunello wine, and discover the town's artisan shops and historic churches. Walking through local markets and scenic countryside paths is frequently suggested for visitors.
How is the weather in Montalcino?
Montalcino has a temperate climate with warm summers and cooler winters, typical of inland Tuscany. It is helpful to pack layers, as evening breezes can feel cooler even in warmer months.
When is the best time to visit Montalcino?
Late spring and early fall are often recommended for comfortable temperatures and vibrant landscapes. Harvest season draws visitors for wine-related activities, while summer highlights outdoor events and festivities.
What are the best places to visit in Montalcino?
Many visitors explore the Fortress of Montalcino, stroll through the old town, and take in the views from Piazza del Popolo. The Museo Civico and nearby historic churches are frequently suggested spots.
What are some hiking trails in Montalcino?
Montalcino has gentle countryside paths winding through vineyards, oak groves, and rolling hills. Many guests enjoy walking trails that start near the town center and offer panoramic views of the Tuscan landscape.
What are some family activities we can do in Montalcino?
Montalcino has relaxed piazzas, scenic fortress walks, and local museums that often welcome families. Exploring nearby farms, sampling gelato in the historic center, or joining a gentle countryside tour can be enjoyable for all ages.
What are some of the best day trip ideas from Montalcino?
Many guests explore nearby villages known for historic architecture, visit regional thermal baths, or tour scenic vineyards in the Tuscan countryside. Montepulciano and Pienza are often recommended for cultural and culinary discoveries.
Are there any pet friendly accommodations available in Montalcino?
Pet-friendly rentals can be found in and around Montalcino, from townhouses to country villas. Many hosts welcome travelers with pets; always confirm amenities in advance.
What are some local tips for visiting Montalcino?
Wear comfortable shoes for strolling hilly streets, and plan visits to both the town center and surrounding countryside for a fuller experience. Join a regional wine tasting and inquire about seasonal festivals for unique local activities.
What is Montalcino known for?
Montalcino is known for its locally crafted Brunello wine, medieval architecture, and hilltop views of Tuscany. The historic village draws visitors with its culinary traditions and scenic landscapes.
What are the best hidden gems to explore in Montalcino?
Montalcino has small artisan shops, lesser-known vineyards, and quiet hillside chapels that invite discovery. Wandering cobbled side streets or visiting local olive oil producers provides a deeper look into community traditions.
What are the best foods to try in Montalcino?
Try locally made pecorino cheese, hearty Tuscan soups, and handmade pasta such as pici. Brunello di Montalcino wine pairs well with traditional stews, wild boar dishes, and seasonal produce.
What should I bring for a trip to Montalcino?
Pack layered clothing for changeable weather, comfortable walking shoes for cobbled streets, and a light jacket for cool evenings. Bringing a reusable water bottle and a small daypack helps with town explorations and countryside excursions.
What is the nightlife in Montalcino like?
Nightlife in Montalcino centers on cozy wine bars, relaxed cafés, and occasional live music venues around the town center. Evening gatherings often celebrate local wines and regional fare in a casual, welcoming atmosphere.
What are the most popular events or festivals in Montalcino?
The Sagra del Tordo archery festival and seasonal wine celebrations like Benvenuto Brunello are often highlighted by locals. Summer music concerts and regional harvest events around Tuscany are also frequently suggested.
Are there family friendly vacation rentals in Montalcino?
Montalcino has family-friendly stays, including country homes and apartments near the town center. Many accommodations provide space for groups and amenities suited to travelers with children.
Destinations to explore
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- Lake Trasimeno
- Lake Bolsena
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Gulf of Baratti
- Del Chianti
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- La Scarzuola
- Antinori nel Chianti Classico
- Siena Cathedral
- CavallinoMatto
- Avignonesi Winery Fattoria Le Capezzine
- Vulci
- Val di Chiana
- Basilica Di San Miniato A Monte
- Palazzo Pubblico
- Valdichiana Outlet Village
- Saturnia Thermal Park
- Rimigliano Natural Park
- Riserva Naturale Diaccia Botrona
- Terme San Filippo
- Things to do Montalcino
- Things to do Siena
- Tastings Siena
- Museums Siena
- Food tours Siena
- Cultural tours Siena
- Art workshops Siena
- Outdoors Siena
- Dining Siena
- Landmarks Siena
- Wildlife Siena
- Cooking Siena
- Things to do Tuscany
- Water sports Tuscany
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