Montepulciano Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Montepulciano

Bellarmino Boutique Apartments

Montepulciano
The price is NZ$177
includes taxes & fees
14 Dec - 15 Dec
Bellarmino Boutique Apartments

Residenza Fabroni

Montepulciano
8.8 out of 10, Excellent, (93)
"Excellent location. Great accommodations "
United States
Susanne
The price is NZ$168
includes taxes & fees
18 Nov - 19 Nov
Residenza Fabroni

Il Tosco

Montepulciano
10.0 out of 10, Exceptional, (112)
"Stunning views. Excellent hostess! Fabulous breakfast!! Would definitely stay again if ever back"
Canada
stephen
The price is NZ$463
includes taxes & fees
18 Nov - 19 Nov
Il Tosco

Osteria del Borgo

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

Charming House in the heart of Montepulciano

Montepulciano
9.8 out of 10, Exceptional, (64)
"The home was charming, spacious, and perfectly located. The host was responsive and helpful, making our stay comfortable and easy. A perfect spot to experience Tuscany—highly recommend!"
United States
Hank T.
Charming House in the heart of Montepulciano

Typical villa with private pool in a panoramic position in southern Tuscany, a few kilometres from t

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

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Montepulciano
9.6 out of 10, Exceptional, (81)
"Enjoyed our stay. Especially the spectacular views of the nearby area. Short walk up to the city center. Great recommendations for restaurants to try from the host. There was a heat wave while during our time and the small AC units didn't do much to cool things down, but we survived! "
United States
Jill B.
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Panoramic villa surrounded by vineyards and olive groves, 6 km from Montepulciano. Ideal for familie

Montepulciano
9.6 out of 10, Exceptional, (4)
"My two friends and I enjoyed our stay at San Bono. The highlight was having the family make and serve us an authentic Tuscan meal! The view is amazing and the location was perfect!"
United States
Flourish Flowers
Panoramic villa surrounded by vineyards and olive groves, 6 km from Montepulciano. Ideal for familie

Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano

Montepulciano
9.8 out of 10, Exceptional, (8)
"We had a fantastic stay for 2 nights. Perfectly located in the heart of the town. Comfortable rooms of lots of space. "
United States
Lorenzo P.
Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano

LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center

Montepulciano (SI)
9.6 out of 10, Exceptional, (53)
"Great location with amazing views over beautiful Tuscan valley. Small quaint accommodation just what you need to be this close to the main square."
Australia
Robyn M.
LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center

Hotel San Gregorio

3.0 star property
Pienza
9.4 out of 10, Exceptional, (133)
"Excellent property! Very elegant and the service was wonderful. The breakfast was also excellent. The location could not be any better - the entry to the old town is just across from the hotel. Wish we could have stayed longer."
United States
DEBORAH
The price is NZ$357
includes taxes & fees
5 Dec - 6 Dec
Hotel San Gregorio

Abbadia Sicille Relais

4.0 star property
Trequanda
8.8 out of 10, Excellent, (163)
"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 NZ$161
includes taxes & fees
3 Dec - 4 Dec
Abbadia Sicille Relais

Farmhouse in the hills with panoramic view and swimming pool

Ristonchia
9.6 out of 10, Exceptional, (75)
"Pros: Location Excellent pool Fantastic views Cons: Very, very outdated kitchen. Limited privacy due to people staying in outbuildings some of the time. A (not unfriendly) cat that's fed at the property and it seems to be assumed that guests will do this. There's a strong smell of cats in the kitchen and the area immediately outside it. Doors can't be left open to ventilate the property when using the pool as the cat may get inside. No consumables apart from toilet roll and cat food: not so...
United Kingdom
Calum S.
Farmhouse in the hills with panoramic view and swimming pool

Casanova - Panoramic Rooms and Suites

3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (78)
"Delightful stay. The room was lovely, and the view from our private terrace was wonderful. Dinner was first rate. Easily walkable into San Quirico, short drive to Montalcino, Pienza, and Montalcino. Nice massage and spa. A very good value."
United States
Charles
The price is NZ$361
includes taxes & fees
19 Nov - 20 Nov
Casanova - Panoramic Rooms and Suites

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Siena
9.4 out of 10, Exceptional, (67)
"Just did a 2 week trip In Italy and this was by far our favorite place to stay. Ready to go back already. Don’t think twice….JUST BOOK IT!"
United States
Blake R.
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Hilltop house in the heart of Tuscany with private pool

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

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

chiusi
10.0 out of 10, Exceptional, (54)
"Our group of 15 thoroughly enjoyed our stay. The communication prior to and during the visit was excellent. The villa is stunning and HUGE and the grounds are magnificent. One day of our trip was spent just relaxing on the property and it was precious time well spent. "
United States
Mindy K.
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

The House of Alice, charm and relaxation

Montalcino (SI)
9.8 out of 10, Exceptional, (66)
"We loved our stay in this beautiful apartment. The town was so quiet and peaceful. Definitely a spot we’d like to visit again"
Canada
Nathan E.
The price is NZ$440
includes taxes & fees
19 Nov - 20 Nov
The House of Alice, charm and relaxation

Il Poggio dell'Eremita

Sinalunga
10.0 out of 10, Exceptional, (57)
"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."
United States
Vivian K.
The price is NZ$282
includes taxes & fees
17 Nov - 18 Nov
Il Poggio dell'Eremita

Villa in Montalcino, exclusive for you, stunning view!!!

Montalcino
10.0 out of 10, Exceptional, (86)
"We were a group of 4 couples and found there was plenty of room for all of us. The property as better in person than we had expected. We had a car so it was really easy to get around and see all the towns nearby. Very beautiful property with great vistas. So relaxing to hang out at the pool or the deck."
Canada
Elfrieda S.
Villa in Montalcino, exclusive for you, stunning view!!!
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.
Save an average of 15% on thousands of hotels when you're signed in

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 favorite 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 depends 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 NZ$161 per night. Entering your travel dates in the search wizard you might find 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 51 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.