Search Holiday Rentals in Montepulciano

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Our top choices for Montepulciano holiday rentals

Townhouse in Montepulciano

Meublé Il Riccio
9.8 out of 10, Exceptional, (86)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is 2.439.768 ₫
2.807.450 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Residenza Fabroni

Townhouse in Montepulciano

La Locanda di San Francesco
9.8 out of 10, Exceptional, (130)
"Great room-great staff-great location"
United States
Richard
The price is 4.885.233 ₫
5.497.293 ₫ total
includes taxes & fees
29 Dec - 30 Dec
La Locanda di San Francesco

Residence in Montepulciano

Delcorto Suites
10.0 out of 10, Exceptional, (32)
"Exceptional service great building felt like a Medici!"
United States
gaetano
The price is 4.713.994 ₫
5.309.099 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Delcorto Suites

Residence in Montepulciano

Il Tosco
10.0 out of 10, Exceptional, (115)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is 6.983.695 ₫
7.805.770 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Il Tosco

Townhouse in Montepulciano

Bed & Breakfast Vicolo dell'Oste
9.6 out of 10, Exceptional, (128)
"Great hosts, central location "
United States
Alexander
The price is 3.088.401 ₫
3.520.777 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Bed & Breakfast Vicolo dell'Oste

Apartment in Montepulciano

Mery s House Elegant Apartment
The price is 8.627.000 ₫
13.287.436 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Mery s House Elegant Apartment
The price is 5.250.142 ₫
5.898.861 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Charming 1-bed Apartment in Montepulciano

Apartment in Montepulciano

Bellarmino Boutique Apartments
6.0 out of 10, (1)
"Heat didnt work, it was FREEZING. Contact didnt seem to be local, seemed like they were managing remotely and couldnt or wouldnt send anyone to help. Nor did they really seem to care. Beautiful area though!"
United States
JON
The price is 2.628.726 ₫
3.015.304 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Bellarmino Boutique Apartments
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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Top Montepulciano Hotel Reviews

Frequently asked questions

Are there holiday rentals in Montepulciano?

Yes, there are holiday rentals close to the most popular sights in Montepulciano, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Montepulciano speak positively about the countryside and wineries in this destination. Make sure you have time to check out the sightseeing tours and festivals during your trip.

How many holiday rentals are there in Montepulciano?

Expedia has 37 holiday rentals for your stay in Montepulciano.

What’s there to see and do in Montepulciano?

Terme di Montepulciano Spa and Val di Chiana are a couple of scenic spots to enjoy the outdoors, whereas Civic Museum is one of the cultural attractions. While here, Palazzo Avignonesi and Cantina del Redi are other places worth a visit.

What’s a holiday rental in Montepulciano like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montepulciano. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family gatherings.