Montepulciano Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Montepulciano vacation rentals

Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (139 reviews)
"Beautiful quaint place to stay in Montepulciano. Stairs are doable to carry up luggage and the views of the valley are spectacular. Great location, can’t wait to stay again!"
Canada
Melissa
The price is CA $230
CA $260 total
includes taxes & fees
Jun 21 - Jun 22
La Locanda di San Francesco
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (98 reviews)
"An amazingly beautiful and historic property. Our room had an incredible view. The staff was fantastic- welcoming and helpful. The location is spectacular. I highly recommend. "
United States
Hallie
The price is CA $228
CA $257 total
includes taxes & fees
Jun 21 - Jun 22
Meublé Il Riccio
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (36 reviews)
"Time transported to the Renaissance at this beautiful, well-kept palazzo… Riccardo’s family did a truly amazing job restoring this place and the facilities are modern & without any discomfort."
American Samoa
Melissa Hyun Joo
The price is CA $272
CA $306 total
includes taxes & fees
May 24 - May 25
Delcorto Suites
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (134 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is CA $173
CA $197 total
includes taxes & fees
May 26 - May 27
Bed & Breakfast Vicolo dell'Oste
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (102 reviews)
"Beautiful apartment, well located, best host and yummy breakfast in a beautiful cafeteria close by. "
United States
Johanna
The price is CA $126
CA $145 total
includes taxes & fees
Jun 9 - Jun 10
Residenza Fabroni
Property entrance

Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (121 reviews)
"Beautiful hotel in the best location. We so enjoyed our stay, especially the amazing breakfast and sweets they had available all day long."
United States
Margaret
The price is CA $380
CA $424 total
includes taxes & fees
May 25 - May 26
Il Tosco
Front of property

montorio

montorio
Montepulciano
9.6 out of 10, Exceptional, (5 reviews)
"The views from this property were amazing. The rooms were clean and felt very homey. "
United States
Lori
The price is CA $175
CA $199 total
includes taxes & fees
Jun 10 - Jun 11
montorio
Deluxe Apartment, 2 Bedrooms, Balcony | View from room

Bellarmino Boutique Apartments

Bellarmino Boutique Apartments
Montepulciano
8.0 out of 10, Very good, (2 reviews)
"I wish I knew more about the check in process ahead of time of that they contacted me ok WhatsApp. But it was clean, comfortable, as pictured, great location, and a great stay. "
United States
Nicole
The price is CA $98
CA $114 total
includes taxes & fees
Jun 8 - Jun 9
Bellarmino Boutique Apartments
Suite, 2 Bedrooms | Courtyard view

L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (24 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is CA $1,008
CA $1,116 total
includes taxes & fees
Jun 9 - Jun 10
L'Olmo
Monolocale Exclusive, vista città, secondo piano senza ascensore

TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (2 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is CA $142
CA $163 total
includes taxes & fees
Jun 14 - Jun 15
TuscanyLettings Studio&Room
Exterior

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (93 reviews)
"Great location, nice room, and great host!"
United States
Chris
The price is CA $206
CA $233 total
includes taxes & fees
May 24 - May 25
B&B Le Scalette di Piazza
1 treatment room, massages

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (85 reviews)
"We loved our stay and wish we could have stayed longer. Our room was clean & comfortable. The view was AMAZING. We had breakfast included daily which was very good and had a bunch of gluten free options. Our bodies were tired after the hustle & bustle of Florence & Rome so we booked into the “light spa” and had the hot pools to ourselves. It was a short walk to town. We wish we could have stayed longer and plan to be back. "
Canada
Ron
The price is CA $259
CA $292 total
includes taxes & fees
Jun 5 - Jun 6
Casanova - Panoramic Rooms and Suites
Studio | Terrace/patio

La Dimora di Dida

La Dimora di Dida
Seggiano
The price is CA $93
CA $102 total
includes taxes & fees
May 27 - May 28
La Dimora di Dida
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (175 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is CA $156
CA $177 total
includes taxes & fees
May 28 - May 29
Abbadia Sicille Relais
Food and drink

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (143 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is CA $269
CA $306 total
includes taxes & fees
Jun 7 - Jun 8
Hotel San Gregorio
Lunch and dinner served, local cuisine

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
The price is CA $386
CA $431 total
includes taxes & fees
May 23 - May 24
Castello di Gargonza
Seasonal outdoor pool

Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
The price is CA $306
CA $344 total
includes taxes & fees
Jun 3 - Jun 4
Albergo Diffuso Borgo Santo
Exterior

Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (6 reviews)
"Loved everything about my stay"
United States
Svetlana
The price is CA $233
CA $276 total
includes taxes & fees
May 28 - May 29
Corte Francigena - Apartments
Exterior

La Locanda Di Cetona

La Locanda Di Cetona
Cetona
9.4 out of 10, Exceptional, (6 reviews)
"A lovely hotel and very welcoming staff. Cetona is a delight. "
Australia
Julian
The price is CA $196
CA $216 total
includes taxes & fees
Jun 2 - Jun 3
La Locanda Di Cetona
Courtyard

Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (5 reviews)
"Amazing stay at this hotel I would recommend it. Great hospitality, clean and picture postcard views. "
United Kingdom
Liam
The price is CA $482
CA $533 total
includes taxes & fees
May 25 - May 26
Fontelunga Hotel & Villas
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montepulciano Hotel Reviews

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent
"Amazing location, very accommodating, clean and good breakfast"
Sandeep 3-night trip
Posted 14 hours ago
Relais Villa Grazianella - UNA Esperienze

Find out more about Montepulciano

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Montepulciano. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Montepulciano?

Yes, we offer vacation rentals close to top sights in Montepulciano, or you can go with a more remote option if you're looking for relaxation. 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 vacation home rentals that Montepulciano has to offer?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This highly rated vacation home rental in Montepulciano is located in the city center and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a terrace, a garden, and a selection of books so you can immerse yourself in your vacation. Another good choice for your trip to Montepulciano is Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano.

How many vacation rentals are there in Montepulciano?

Expedia has 31 vacation 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 Piazza Grande are other places worth a visit.

What’s a vacation rental in Montepulciano like?

A vacation rental is a private property you can book for a few weeks or just a few days in Montepulciano. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.