Montepulciano Holiday Rentals

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Holiday Rentals in Montepulciano

Apartment in Montepulciano

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 AU$184
includes taxes & fees
9 Dec - 10 Dec
Bellarmino Boutique Apartments

Residence in Montepulciano

8.8 out of 10, Excellent, (93)
"We had a great stay! Beautiful on the roof top terrace!"
United States
Jennifer
The price is AU$147
includes taxes & fees
9 Dec - 10 Dec
Residenza Fabroni

Residence in Montepulciano

10.0 out of 10, Exceptional, (114)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is AU$443
includes taxes & fees
8 Dec - 9 Dec
Il Tosco

Residence in Montepulciano

9.0 out of 10, Wonderful, (156)
"Staff and location were both excellent."
United States
Nicholas
Osteria del Borgo

Villa in Montepulciano

9.6 out of 10, Exceptional, (4)
"This was one of the highlights of our 3 week trip. The surroundings were beautiful and the hosts who only spoke Italian were absolutely lovely. We were about 15 minutes from Montepuciano in a quiet farm area. One night we had the hosts cook us an anniversary dinner for our friends which was so much fun. Highly recommended. "
United States
Debbie C.
Panoramic villa surrounded by vineyards and olive groves, 6 km from Montepulciano. Ideal for familie

Apartment in Montepulciano

9.8 out of 10, Exceptional, (65)
"Location, location, location. The room was great. The host was easy to communicate with and was very helpful."
United States
peter m.
Charming House in the heart of Montepulciano

Villa in Montepulciano

10.0 out of 10, Exceptional, (2)
"The villa is spacious with big bedrooms and five good bathrooms. The kitchen is well equipped and our big family with 8 adults and 6 children had everything we needed for our 14-day stay. There is a big pool beautifully located in a separate part of the garden. The trees and bushes give shadow all through the day so there is no need for umbrellas. The whole property is well cared for by the very friendly owners who live nearby. This is a perfect location for a visit in Toscana, close to many...
Sweden
Kristina M.
Typical villa with private pool in a panoramic position in southern Tuscany, a few kilometres from t

Holiday Home in Montepulciano

9.6 out of 10, Exceptional, (81)
"This house and location was perfect. Beautiful views and a great kitchen. Montepulciano was our favorite town that we visited on our trip. Easy check in and the host had a document that she sent us that had a lot of great info."
United States
Tom K.
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Holiday Home in Montepulciano

9.8 out of 10, Exceptional, (8)
"Absolutely loved this property. It’s in a great location and has so much character. "
United States
Randy C.
Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano

Apartment in Montepulciano (SI)

9.6 out of 10, Exceptional, (53)
"This was an ideal little find, centrally located across from the Fortezza and behind the historic town center. The space was perfect for a two-person stay."
United States
Lynne S.
LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center

Residence in Pienza

3.0 star property
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is AU$350
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio

Residence in Trequanda

4.0 star property
8.8 out of 10, Excellent, (164)
"We stayed there for 1 night our our way to Rome. BEAUTIFUL. Bed was very comfortable as well. 10/10 will recommend to everyone "
United States
Brittnay
The price is AU$135
includes taxes & fees
14 Dec - 15 Dec
Abbadia Sicille Relais

Holiday Home in Ristonchia

9.6 out of 10, Exceptional, (75)
"Was wonderful and beautiful. "
United States
Alana A.
Farmhouse in the hills with panoramic view and swimming pool

Villa in Siena

9.4 out of 10, Exceptional, (67)
"What a lovely place, I will recommend this fabulous home to friends and family and will be returning sometime soon."
United Kingdom
peter H.
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Residence in San Quirico d'Orcia

3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
The price is AU$321
includes taxes & fees
11 Dec - 12 Dec
Casanova - Panoramic Rooms and Suites

Villa in chiusi

10.0 out of 10, Exceptional, (57)
"We had a very nice stay and a well organized pizza night in the villa. Glad to come again:) "
Germany
Florian Maria W.
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

Holiday Home in Montalcino (SI)

9.8 out of 10, Exceptional, (66)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
The price is AU$376
includes taxes & fees
7 Dec - 8 Dec
The House of Alice, charm and relaxation

Villa in Sinalunga

10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is AU$251
includes taxes & fees
20 Dec - 21 Dec
Il Poggio dell'Eremita

Villa in Montisi

9.8 out of 10, Exceptional, (94)
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."
United States
Timothy C.
Hilltop house in the heart of Tuscany with private pool

Villa in Toscane

10.0 out of 10, Exceptional, (13)
"Beautiful property with the most amazing pool, our hosts were so lovely and helpful, always at hand if we needed anything. I would recommend for a very relaxing holiday."
United States
Maxine B.
Country House With Private Pool
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

Find out more about Montepulciano

Everything you need to know about Montepulciano holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montepulciano holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montepulciano holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Montepulciano holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montepulciano. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montepulciano holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montepulciano holiday rentals we have selected for you start as low as AU$135 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Montepulciano rentals

At Expedia, we put the best Montepulciano holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Montepulciano rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montepulciano holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montepulciano. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

What are some of the best holiday rentals that Montepulciano has to offer?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This highly rated holiday home rental in Montepulciano is located in the city centre, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a terrace, a garden and a selection of books so that you can immerse yourself in your holiday. Another good choice for your trip to Montepulciano is Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano.

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.