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Featured Holiday Homes in Montepulciano

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
Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano

Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano

Montepulciano Provincia di Siena
A stay at this vacation home places you in the heart of Montepulciano, steps from Val di Chiana and Cantina Contucci.
Opens in a new windowEntire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano
Period residence in Montepulciano (Siena), Tuscany

Period residence in Montepulciano (Siena), Tuscany

Montepulciano Provincia di Siena
With a stay at this vacation home in Montepulciano, you'll be just steps from Val di Chiana and Torre di Pulcinella.
Opens in a new windowPeriod residence in Montepulciano (Siena), Tuscany
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Stefania Townhouse Luxury 2 Bedrooms Apartment

Stefania Townhouse Luxury 2 Bedrooms Apartment

Montepulciano Toscana
With a stay at this vacation home in Montepulciano, you'll be just steps from Val di Chiana and Torre di Pulcinella.
Opens in a new windowStefania Townhouse Luxury 2 Bedrooms Apartment
Stunning private villa for 4 guests with WIFI, TV and pets allowed

Stunning private villa for 4 guests with WIFI, TV and pets allowed

Montepulciano Tuscany
With a stay at this vacation home in Montepulciano, you'll be just steps from Val di Chiana and Torre di Pulcinella.
Opens in a new windowStunning private villa for 4 guests with WIFI, TV and pets allowed
Casa Campau by Interhome

Casa Campau by Interhome

Montepulciano
A stay at this vacation home places you in the heart of Montepulciano, steps from Val di Chiana and Torre di Pulcinella.
Opens in a new windowCasa Campau by Interhome
Tranquil Stay in Montepulciano

Tranquil Stay in Montepulciano

Acquaviva Montepulciano
Located in Montepulciano, this vacation home is on a lake, within a 15-minute drive of Val di Chiana and Tenuta Valdipiatta.
Opens in a new windowTranquil Stay in Montepulciano
Belvilla by OYO Chiaraquattro

Belvilla by OYO Chiaraquattro

Montepulciano SI
With a stay at this vacation home in Montepulciano, you'll be within a 15-minute drive of Val di Chiana and Tenuta Valdipiatta.
Opens in a new windowBelvilla by OYO Chiaraquattro
Il Saragio open space in the Tuscan countryside

Il Saragio open space in the Tuscan countryside

Montepulciano Toscana
Located in Montepulciano, this vacation home is in a rural location, within a 15-minute drive of Val di Chiana and Tenuta Valdipiatta.
Opens in a new windowIl Saragio open space in the Tuscan countryside
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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.

Montepulciano 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 Montepulciano vacation homes are the perfect way for you to wing it.

Holiday houses in Montepulciano 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 Montepulciano 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 Montepulciano adventures, obvs.

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

Montepulciano Holiday Homes essential information

Accommodation
40 Holiday Homes
Lowest Price
AU$251
Highest Price
AU$1,062
Popular accommodation
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING, Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano, Period residence in Montepulciano (Siena), Tuscany , Stefania Townhouse Luxury 2 Bedrooms Apartment , Stunning private villa for 4 guests with WIFI, TV and pets allowed, Casa Campau by Interhome, Tranquil Stay in Montepulciano, Belvilla by OYO Chiaraquattro, Il Saragio open space in the Tuscan countryside

Top trending hotels in Montepulciano

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI
The price is AU$251 per night from 14 Dec to 15 Dec
AU$251
14 Dec - 15 Dec
includes taxes & fees
Located in Montepulciano, Relais Villa Grazianella - UNA Esperienze is in a rural location, within a 15-minute drive of Val di Chiana and Terme di Montepulciano ...
Opens in a new windowRelais Villa Grazianella - UNA Esperienze
Albergo San Biagio

Albergo San Biagio

3 out of 5
Via San Bartolomeo 2 Montepulciano SI
Fully refundableReserve now, pay when you stay
The price is AU$1,062 per night from 31 Dec to 1 Jan
AU$1,062
31 Dec - 1 Jan 2026
includes taxes & fees
A stay at Albergo San Biagio places you in the heart of Montepulciano, steps from Val di Chiana and 8 minutes by foot from San Biagio.
Opens in a new windowAlbergo San Biagio
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10 Montepulciano SI
Located in Montepulciano, Precise Tale Poggio Alla Sala is in a rural location, a 1-minute drive from Val di Chiana and 7 minutes from Terme Sant'Elena.
Opens in a new windowPrecise Tale Poggio Alla Sala
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Villa Svetoni Wine Resort

Villa Svetoni Wine Resort

Via Umbria 65 Montepulciano SI
Fully refundableReserve now, pay when you stay
Located in Montepulciano, Villa Svetoni Wine Resort is in a rural location, a 1-minute drive from Val di Chiana and 5 minutes from Tenuta Valdipiatta.
Opens in a new windowVilla Svetoni Wine Resort
Don't see what you're looking for?
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.