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Featured Holiday Homes in Montalcino

Borgo Argiano

Borgo Argiano

Loc. Argiano Castelnuovo Berardenga SI
Located in Castelnuovo Berardenga, Borgo Argiano is on a river, within a 10-minute drive of Chianti Sculpture Park and La Fornace Art Gallery.
Opens in a new windowBorgo Argiano
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Montepulciano Siena
A stay at this vacation home places you in the heart of Montepulciano, steps from Val di Chiana and 4 minutes by foot from Cantina Contucci.
Opens in a new windowINDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
Il Palazzetto

Il Palazzetto

Strada del Lucherino, 31 Siena SI
Located in Siena, Il Palazzetto is in a rural location, within a 5-minute drive of Orto Botanico dell'Universita di Siena and Sant'Agostino Monastery.
Opens in a new windowIl Palazzetto
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Welcome to Villa Dolce Vita - your private paradise in Tuscany

Welcome to Villa Dolce Vita - your private paradise in Tuscany

Pieve Vecchia Tuscany
Located in Lucignano, this vacation home is in a rural location, within a 5-minute drive of Piazza del Tribunal and Museum of Lucignano.
Opens in a new windowWelcome to Villa Dolce Vita - your private paradise in Tuscany
Beautiful stone house with garden and private pool.

Beautiful stone house with garden and private pool.

Sovicille - Siena Toscana
Located in Siena, this vacation home is in a rural location, within a 15-minute drive of Val di Merse and Piccolomini Library.
Opens in a new windowBeautiful stone house with garden and private pool.
Private House with Exclusive Swimming Pool Heated and Amazing View

Private House with Exclusive Swimming Pool Heated and Amazing View

Boccheggiano Toscana
When you stay at this vacation home in Montieri, you'll be by the sea and 12 minutes by car from Val di Merse.
Opens in a new windowPrivate House with Exclusive Swimming Pool Heated and Amazing View
House in Val d'Orcia perfect for relaxation CIN IT052024C2APXZK7PD

House in Val d'Orcia perfect for relaxation CIN IT052024C2APXZK7PD

RADICOFANI
Located in Radicofani, this vacation home is in a rural location, a 2-minute drive from Val di Chiana and 9 minutes from Rocca di Radicofani.
Opens in a new windowHouse in Val d'Orcia perfect for relaxation CIN IT052024C2APXZK7PD
Your dream home! In harmony with nature!  Priv. Pool - fantastic views!

Your dream home! In harmony with nature! Priv. Pool - fantastic views!

Arcidosso Toskana
Located in Arcidosso, this vacation home is in a rural location, within a 15-minute walk of Mount Amiata Fauna Park and Castle Arcidosso.
Opens in a new windowYour dream home! In harmony with nature! Priv. Pool - fantastic views!
The House of Alice, charm and relaxation

The House of Alice, charm and relaxation

Montalcino (SI) Toscana
Located in Montalcino, this vacation home is by the sea, a 4-minute drive from Abbazia di Sant'Antimo and 9 minutes from Museum of Brunello.
Opens in a new windowThe House of Alice, charm and relaxation
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Montalcino Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Montalcino vacation homes are the perfect way for you to wing it.

Holiday houses in Montalcino let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Montalcino in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Montalcino adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Montalcino with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Montalcino vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Montalcino Holiday Homes essential information

Accommodation
1329 Holiday Homes
Lowest Price
AU$218
Highest Price
AU$3,398
Popular accommodation
Borgo Argiano, INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING, Il Palazzetto, Welcome to Villa Dolce Vita - your private paradise in Tuscany, Beautiful stone house with garden and private pool., Private House with Exclusive Swimming Pool Heated and Amazing View, House in Val d'Orcia perfect for relaxation CIN IT052024C2APXZK7PD , Your dream home! In harmony with nature! Priv. Pool - fantastic views!, The House of Alice, charm and relaxation

Top trending hotels in Montalcino

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

5 out of 5
Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
The price is AU$1,127 per night from 31 May to 1 June
AU$1,127
31 May - 1 June
includes taxes & fees
Located in Montalcino, Castello di Velona Resort Thermal SPA & Winery is in a national park, within a 15-minute drive of Abbazia di Sant'Antimo and Fortress ...
Opens in a new windowCastello di Velona Resort Thermal SPA & Winery
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

5 out of 5
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
The price is AU$3,398 per night from 25 May to 26 May
AU$3,398
25 May - 26 May
includes taxes & fees
With a stay at Castiglion del Bosco, A Rosewood Hotel in Montalcino, you'll be 7.8 mi (12.5 km) from Fortress of Montalcino and 11.7 mi (18.8 km) from Monte ...
Opens in a new windowCastiglion del Bosco, A Rosewood Hotel
SI Montalcino Hotel

SI Montalcino Hotel

3 out of 5
Via Osticcio 21 Montalcino SI
Fully refundableReserve now, pay when you stay
The price is AU$218 per night from 17 June to 18 June
AU$218
17 June - 18 June
includes taxes & fees
Located in Montalcino, SI Montalcino Hotel is a 2-minute drive from Fortress of Montalcino and 6 minutes from Poggio Antico.
Opens in a new windowSI Montalcino Hotel
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Mastrojanni Relais - Small Luxury Hotels of the World

Mastrojanni Relais - Small Luxury Hotels of the World

Localita Loreto e San Pio Montalcino SI
Fully refundableReserve now, pay when you stay
The price is AU$959 per night from 19 May to 20 May
AU$959
19 May - 20 May
includes taxes & fees
Located in Montalcino, Mastrojanni Relais - Small Luxury Hotels of the World is in the mountains, within a 15-minute drive of Museum of Brunello and Abbazia ...
Opens in a new windowMastrojanni Relais - Small Luxury Hotels of the World
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.