Montepulciano Vacation Rentals

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Check prices for these dates

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Montepulciano vacation rentals

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Residenza Fabroni

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is ￥13,749
￥15,862 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Residenza Fabroni
Premium bedding, down comforters, minibar, in-room safe
La Locanda di San Francesco

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (131)
"Great room-great staff-great location"
United States
Richard
The price is ￥27,062
￥30,505 total
includes taxes & fees
Jan 18 - Jan 19, 2026
La Locanda di San Francesco
Exterior
Meublé Il Riccio

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (86)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio
Exterior
Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (128)
"Great hosts, central location "
United States
Alexander
Bed & Breakfast Vicolo dell'Oste
Interior
Delcorto Suites

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (33)
"Exceptional service great building felt like a Medici!"
United States
gaetano
The price is ￥31,388
￥35,264 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Delcorto Suites
Property entrance
Il Tosco

Il Tosco

Il Tosco
Montepulciano
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 ￥40,790
￥45,606 total
includes taxes & fees
Dec 30 - Dec 31
Il Tosco
Deluxe Apartment, 2 Bedrooms, Balcony | Free WiFi, bed sheets
Bellarmino Boutique Apartments

Bellarmino Boutique Apartments

Bellarmino Boutique Apartments
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 ￥14,527
￥16,717 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Bellarmino Boutique Apartments
Apartment | 2 bedrooms, desk
Mery s House Elegant Apartment

Mery s House Elegant Apartment

Mery s House Elegant Apartment
Montepulciano
The price is ￥53,862
￥81,881 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Mery s House Elegant Apartment
Apartment | View from room
Charming 1-bed Apartment in Montepulciano

Charming 1-bed Apartment in Montepulciano

Charming 1-bed Apartment in Montepulciano
Montepulciano
The price is ￥31,289
￥35,155 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Charming 1-bed Apartment in Montepulciano
Deluxe Double Room | View from room
Affitacamere Maria Gabriella

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (51)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella
Seasonal outdoor pool, an infinity pool, pool umbrellas, sun loungers
FonteLiving

FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (5)
"Comfortable apartment in quiet block. Nicely furnished excellent housekeeping nice spacious bathrooms great view from the terrace."
United Kingdom
R
The price is ￥11,795
￥13,344 total
includes taxes & fees
Jan 13 - Jan 14, 2026
FonteLiving
Daily buffet breakfast (EUR 10 per person)
DormiVeglia B&B

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (27)
"This was our favourite B&B. The owner Simona was absolutely wonderful. The hot tub in our room was out of this world. If you have the chance to visite this gem…DO IT!!"
Canada
Claude
DormiVeglia B&B
View from room
Abbadia Sicille Relais

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ￥10,888
￥12,530 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Abbadia Sicille Relais
Breakfast, lunch, dinner served; local cuisine
Hotel San Gregorio

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
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 ￥29,386
￥33,430 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hotel San Gregorio
Pillowtop beds, minibar, in-room safe, individually decorated
La Locanda Di Cetona

La Locanda Di Cetona

La Locanda Di Cetona
Cetona
9.2 out of 10, Wonderful, (5)
"A lovely hotel and very welcoming staff. Cetona is a delight. "
Australia
Julian
La Locanda Di Cetona
Standard Double Room (La Piazza) | Desk, soundproofing, free WiFi, bed sheets
B&B Le Scalette di Piazza

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (90)
"Great location and excellent staff. "
Canada
Jacek
The price is ￥17,793
￥20,309 total
includes taxes & fees
Jan 7 - Jan 8, 2026
B&B Le Scalette di Piazza
Front of property - evening/night
Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
Casanova - Panoramic Rooms and Suites
Suite Bernardo, Panoramica al terzo piano senza ascensore | 1 bedroom, desk, laptop workspace, iron/ironing board
PienzaLettings Suites

PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (1)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is ￥13,409
￥15,487 total
includes taxes & fees
Jan 6 - Jan 7, 2026
PienzaLettings Suites
Bar (on property)
La Piccola Locanda

La Piccola Locanda

La Piccola Locanda
Chiusi
8.8 out of 10, Excellent, (8)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
La Piccola Locanda
Exterior
La Dimora di Dida

La Dimora di Dida

La Dimora di Dida
Seggiano
The price is ￥11,561
￥12,717 total
includes taxes & fees
Jan 7 - Jan 8, 2026
La Dimora di Dida
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

Palazzo Nobile di San Donato

Palazzo Nobile di San Donato

10/10 Excellent
"The staff were very friendly. We enjoyed a lovely breakfast made to order and the hospitality was exceptional. "
Jennifer 1-night trip
Posted 13 days ago
Palazzo Nobile di San Donato

Find out more about Montepulciano

Search for holiday rentals in Montepulciano on Expedia! You can easily find your home rentals, villas, holiday apartments in Montepulciano using one of the methods below:

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Look no further and take a look at our great range of rental properties in Montepulciano!

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 36 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 Cantina del Redi 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.