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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
Tuscan Hilltop Terrace

Tuscan Hilltop Terrace

Montepulciano Provincia di Siena
A stay at this vacation home places you in the heart of Montepulciano, steps from Val di Chiana and Torre del Pulcinella.
Opens in a new windowTuscan Hilltop Terrace
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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
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
Wine Lovers! Luxury House on 250 Acre Vineyard, AC & Private Pool

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

Montepulciano SI Tuscany
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.
Opens in a new windowWine Lovers! Luxury House on 250 Acre Vineyard, AC & Private Pool
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
Villa Montebella in Montepulciano

Villa Montebella in Montepulciano

Montepulciano SI
With a stay at this vacation home in Montepulciano, you'll be steps from Val di Chiana and a 5-minute drive from Tenuta Valdipiatta.
Opens in a new windowVilla Montebella in Montepulciano
Tranquil Stay in Montepulciano

Tranquil Stay in Montepulciano

Montepulciano SI
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 windowTranquil Stay in Montepulciano
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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
35 Holiday Homes
Lowest Price
AU$117
Highest Price
AU$618
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, Tuscan Hilltop Terrace, Period residence in Montepulciano (Siena), Tuscany , Stunning private villa for 4 guests with WIFI, TV and pets allowed, Wine Lovers! Luxury House on 250 Acre Vineyard, AC & Private Pool, Casa Campau by Interhome, Villa Montebella in Montepulciano, Tranquil Stay in Montepulciano

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
The price is AU$618 per night from 6 May to 7 May
AU$618
6 May - 7 May
includes taxes & fees
Located in Montepulciano, Precise Tale Poggio Alla Sala is in a rural location, a 1-minute drive from Val di Chiana and 8 minutes from Terme Sant'Elena.
Opens in a new windowPrecise Tale Poggio Alla Sala
Nuovo Etruria Resort

Nuovo Etruria Resort

Via di S. Martino snc Montepulciano SI
Fully refundableReserve now, pay when you stay
The price is AU$181 per night from 3 May to 4 May
AU$181
3 May - 4 May
includes taxes & fees
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.
Opens in a new windowNuovo Etruria Resort
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI
The price is AU$439 per night from 26 May to 27 May
AU$439
26 May - 27 May
includes taxes & fees
Located in Montepulciano, Relais Villa Grazianella - UNA Esperienze is in a rural location, within a 15-minute drive of Terme di Montepulciano Spa and Archaeological ...
Opens in a new windowRelais Villa Grazianella - UNA Esperienze
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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
The price is AU$117 per night from 3 May to 4 May
AU$117
3 May - 4 May
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
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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.