Montepulciano Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Montepulciano vacation rentals

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 P15,528
P17,355 total
includes taxes & fees
Dec 22 - Dec 23
Il Tosco
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
The price is P7,311
P8,317 total
includes taxes & fees
Dec 23 - Dec 24
Bed & Breakfast Vicolo dell'Oste
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
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 P10,502
P11,827 total
includes taxes & fees
Jan 18 - Jan 19, 2026
La Locanda di San Francesco
Interior
Delcorto Suites

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (32)
"Exceptional service great building felt like a Medici!"
United States
gaetano
The price is P11,645
P13,085 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Delcorto Suites
2 bedrooms, desk
Mery s House Elegant Apartment

Mery s House Elegant Apartment

Mery s House Elegant Apartment
Montepulciano
The price is P20,095
P30,548 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Mery s House Elegant Apartment
Lobby
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 P5,425
P6,242 total
includes taxes & fees
Jan 17 - Jan 18, 2026
Residenza Fabroni
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 P7,904
P8,969 total
includes taxes & fees
Dec 22 - Dec 23
Bellarmino Boutique Apartments
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 P11,673
P13,116 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Charming 1-bed Apartment in Montepulciano
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
Front of property
Idolina Guest House

Idolina Guest House

Idolina Guest House
Montalcino
9.4 out of 10, Exceptional, (105)
"The room met our expectations. Fulvia welcomed us and provided all info we needed. She was lovely and the room spacious and cosy. The location was perfect for our needs and we were very pleased."
United Kingdom
Kathrin
Idolina Guest House
Exterior
L'Antica Sosta

L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3)
"Molto accoglienti e gentili "
Italy
Valentina
The price is P4,084
P4,493 total
includes taxes & fees
Jan 8 - Jan 9, 2026
L'Antica Sosta
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
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 P5,003
P5,778 total
includes taxes & fees
Jan 16 - Jan 17, 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
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 P13,443
P15,200 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hotel San Gregorio
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
Laptop workspace, iron/ironing board, free WiFi
TuscanyLettings Studio&Room

TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (1)
"メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。"
Japan
keita
The price is P5,559
P6,389 total
includes taxes & fees
Jan 6 - Jan 7, 2026
TuscanyLettings Studio&Room
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 P4,444
P5,026 total
includes taxes & fees
Dec 22 - Dec 23
FonteLiving
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
B&B Le Scalette di Piazza
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 6 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.

How many vacation rentals are there in Montepulciano?

Expedia has 37 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.