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Featured Holiday Homes in Montepulciano

A MAGICAL HOLIDAY IN TUSCANY

A MAGICAL HOLIDAY IN TUSCANY

Montepulciano
A stay at this vacation home places you in the heart of Montepulciano, steps from Val di Chiana and Cantina Contucci.
A MAGICAL HOLIDAY IN TUSCANY
Beautiful Residence in the Old Town

Beautiful Residence in the Old Town

Montepulciano
A stay at this vacation home places you in the heart of Montepulciano, steps from Val di Chiana and Cantina Contucci.
Beautiful Residence in the Old Town
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.
Casa Campau by Interhome
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Period residence in Montepulciano (Siena), Tuscany

Period residence in Montepulciano (Siena), Tuscany

Montepulciano
With a stay at this vacation home in Montepulciano, you'll be just steps from Val di Chiana and Torre di Pulcinella.
Period residence in Montepulciano (Siena), Tuscany
Borgo Buio Town House, house in the historic center

Borgo Buio Town House, house in the historic center

Montepulciano
With a stay at this vacation home in Montepulciano, you'll be just steps from Val di Chiana and Torre di Pulcinella.
Borgo Buio Town House, house in the historic center
Belvilla by OYO Chiaraquattro

Belvilla by OYO Chiaraquattro

Acquaviva Montepulciano
Located in Montepulciano, this vacation home is on a lake, within a 15-minute drive of Val di Chiana and Tenuta Valdipiatta.
Belvilla by OYO Chiaraquattro
Only 3 km from Montepulciano lies this pleasant vacation home in an idyllic side valley.

Only 3 km from Montepulciano lies this pleasant vacation home in an idyllic side valley.

Montepulciano SI
With a stay at this vacation home in Montepulciano, you'll be steps from Val di Chiana and a 4-minute drive from San Biagio.
Only 3 km from Montepulciano lies this pleasant vacation home in an idyllic side valley.
Il Saragio open space in the Tuscan countryside

Il Saragio open space in the Tuscan countryside

Montepulciano
Located in Montepulciano, this vacation home is in a rural location, within a 15-minute drive of Val di Chiana and Tenuta Valdipiatta.
Il Saragio open space in the Tuscan countryside
Wine Lovers! Luxury House on 250 Acre Vineyard, AC & Private Pool

Wine Lovers! Luxury House on 250 Acre Vineyard, AC & Private Pool

Montepulciano SI
Located in Montepulciano, this vacation home is in a rural location, a 1-minute drive from Val di Chiana and 6 minutes from Tenuta Valdipiatta.
Wine Lovers! Luxury House on 250 Acre Vineyard, AC & Private Pool
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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
41 Holiday Homes
Lowest Price
AU$101
Highest Price
AU$617
Popular accommodation
A MAGICAL HOLIDAY IN TUSCANY, Beautiful Residence in the Old Town, Casa Campau by Interhome, Period residence in Montepulciano (Siena), Tuscany , Borgo Buio Town House, house in the historic center, Belvilla by OYO Chiaraquattro, Only 3 km from Montepulciano lies this pleasant vacation home in an idyllic side valley., Il Saragio open space in the Tuscan countryside, Wine Lovers! Luxury House on 250 Acre Vineyard, AC & Private Pool

Top trending hotels in Montepulciano

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10, Montepulciano, SI
The price is AU$617 per night from 17 Mar to 18 Mar
AU$617
includes taxes & fees
17 Mar - 18 Mar
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.
Precise Tale Poggio Alla Sala
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$101 per night from 16 Mar to 17 Mar
AU$101
includes taxes & fees
16 Mar - 17 Mar
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.
Albergo San Biagio
Villa Svetoni Wine Resort

Villa Svetoni Wine Resort

Via Umbria 65, Montepulciano, SI
Fully refundable
The price is AU$399 per night from 6 Mar to 7 Mar
AU$399
includes taxes & fees
6 Mar - 7 Mar
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.
Villa Svetoni Wine Resort
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Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5, Via delle tre berte, Montepulciano, SI
The price is AU$303 per night from 18 Mar to 19 Mar
AU$303
includes taxes & fees
18 Mar - 19 Mar
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 ...
Relais Villa Grazianella - UNA Esperienze
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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.