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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
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.
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
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
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
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Il Mulino di Tresa

Il Mulino di Tresa

Via S. Bartolomeo, 26, Montepulciano SI, Tuscany
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.
Il Mulino di Tresa
Stunning private villa for 4 people with WIFI, TV, pets allowed and parking

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

Montepulciano
With a stay at this vacation home in Montepulciano, you'll be just steps from Val di Chiana and Torre di Pulcinella.
Stunning private villa for 4 people with WIFI, TV, pets allowed and parking
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
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
Vintage Mansion in Montepulciano With Pool

Vintage Mansion in Montepulciano With Pool

Montepulciano
With a stay at Vintage Mansion in Montepulciano With Pool in Montepulciano, you'll be within a 15-minute drive of Lake Trasimeno and Val di Chiana.
Vintage Mansion in Montepulciano With Pool
Stefania Townhouse Luxury 2 Bedrooms Apartment

Stefania Townhouse Luxury 2 Bedrooms Apartment

Montepulciano
With a stay at this vacation home in Montepulciano, you'll be just steps from Val di Chiana and Torre di Pulcinella.
Stefania Townhouse Luxury 2 Bedrooms Apartment
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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
51 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING, Borgo Buio Town House, house in the historic center, A MAGICAL HOLIDAY IN TUSCANY, Il Mulino di Tresa, Stunning private villa for 4 people with WIFI, TV, pets allowed and parking, Casa Campau by Interhome, Period residence in Montepulciano (Siena), Tuscany , Vintage Mansion in Montepulciano With Pool, Stefania Townhouse Luxury 2 Bedrooms Apartment

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
Fully refundableReserve now, pay when you stay
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
Nuovo Etruria Resort

Nuovo Etruria Resort

Via di S. Martino snc, Montepulciano, SI
Fully refundableReserve now, pay when you stay
With a stay at Nuovo Etruria Resort in Montepulciano, you'll be a 1-minute walk from Val di Chiana and 14 minutes by foot from Church of St. Agnes.
Nuovo Etruria Resort
Villa Svetoni Wine Resort

Villa Svetoni Wine Resort

Via Umbria 65, Montepulciano, SI
Fully refundable
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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Albergo San Biagio

Albergo San Biagio

3 out of 5
Via San Bartolomeo 2, Montepulciano, SI
Fully refundableReserve now, pay when you stay
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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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.