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Featured Holiday Homes in Montepulciano

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
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
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
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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.
Apartment In A Hotel 'Guest-house Montepulciano' with Wi-Fi and Air Conditioning

Apartment In A Hotel 'Guest-house Montepulciano' with Wi-Fi and Air Conditioning

montepulciano
With a stay at this vacation home in Montepulciano, you'll be just steps from Val di Chiana and Torre di Pulcinella.
Apartment In A Hotel 'Guest-house Montepulciano' with Wi-Fi and Air Conditioning
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$66
Highest Price
AU$365
Popular accommodation
Casa Campau by Interhome, Beautiful Residence in the Old Town, 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., Apartment In A Hotel 'Guest-house Montepulciano' with Wi-Fi and Air Conditioning, Il Saragio open space in the Tuscan countryside, Wine Lovers! Luxury House on 250 Acre Vineyard, AC & Private Pool

Top trending hotels in Montepulciano

Hotel Panoramic

Hotel Panoramic

3 out of 5
Via di Villa Bianca, 8, Montepulciano, SI
The price is AU$172 per night from 27 Dec to 28 Dec
AU$172
includes taxes & fees
27 Dec - 28 Dec
Located in Montepulciano, Hotel Panoramic is in a rural location, just a 1-minute walk from Val di Chiana and a 3-minute drive from San Biagio.
Hotel Panoramic
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10, Montepulciano, Provincia di Siena
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
The price is AU$66 per night from 6 Jan to 7 Jan
AU$66
includes taxes & fees
6 Jan - 7 Jan 2025
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
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Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5, Via delle tre berte, Montepulciano, SI
Fully refundableReserve now, pay when you stay
The price is AU$365 per night from 2 Jan to 3 Jan
AU$365
includes taxes & fees
2 Jan - 3 Jan 2025
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.