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Montisi Holiday Rentals

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Our top choices for Montisi holiday rentals

Townhouse in Montepulciano

Meublé Il Riccio
9.8 out of 10, Exceptional, (86)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio

Townhouse in Cetona

La Locanda Di 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

Townhouse in Chiusi

La Piccola Locanda
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

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is AU$114
includes taxes & fees
11 Jan - 12 Jan 2026
Abbadia Sicille Relais

Townhouse in Montepulciano

La Locanda di San Francesco
9.8 out of 10, Exceptional, (131)
"Great room-great staff-great location"
United States
Richard
The price is AU$273
includes taxes & fees
18 Jan - 19 Jan 2026
La Locanda di San Francesco

Townhouse in Siena City Centre

Al Mercato B&B
9.0 out of 10, Wonderful, (96)
"Hotel is a one block from main square of the city also have a good restaurant around the corner "
United States
Guillermo
The price is AU$153
includes taxes & fees
20 Jan - 21 Jan 2026
Al Mercato B&B

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is AU$151
includes taxes & fees
13 Jan - 14 Jan 2026
Residenza Fabroni

Residence in Pienza

Hotel San Gregorio
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$335
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio

Townhouse in Pienza

Affitacamere Maria Gabriella
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

Townhouse in Siena

Il Pozzo di Sant'Andrea
9.8 out of 10, Exceptional, (16)
"Great host, lovely place near Siena"
United Kingdom
Prem
Il Pozzo di Sant'Andrea

Residence in San Quirico d'Orcia

Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
The price is AU$387
includes taxes & fees
27 Dec - 28 Dec
Casanova - Panoramic Rooms and Suites

Townhouse in Montalcino

B&B Le Scalette di Piazza
9.4 out of 10, Exceptional, (90)
"Great location and excellent staff. "
Canada
Jacek
B&B Le Scalette di Piazza

Residence in Siena City Centre

La Terrazza Sul Campo Rooming House
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House

Townhouse in Monte San Savino

DormiVeglia B&B
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

Townhouse in Montepulciano

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

Townhouse in Siena City Centre

Piazza Paradiso Accomodation
9.2 out of 10, Wonderful, (155)
"What my girlfriend loved the most was the bathtub! We have been busy traveling the last week and a half and she was overjoyed with a chance to soak in a bath tub. Room was spacious and clean, the staff was helpful and friendly. The hotel was centrally located and within easy walking distance to Piazza del Campo. Looking forward to staying with Piazza Paradiso accommodation again. We will definitely recommend Piazza Paradiso to all our friends visiting Siena!"
United States
Niels G.
Piazza Paradiso Accomodation
9.0 out of 10, Wonderful, (46)
"Our stay was great. "
United States
Elena
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Townhouse in Siena City Centre

Palazzo Masi
8.8 out of 10, Excellent, (84)
"Very friendly and attentive, a very clean place and its location is excellent. "
United States
Gloria
The price is AU$165
includes taxes & fees
2 Jan - 3 Jan 2026
Palazzo Masi

Apartment in Montalcino

Corte Francigena
9.8 out of 10, Exceptional, (6)
"Loved everything about my stay"
United States
Svetlana
The price is AU$291
includes taxes & fees
25 Dec - 26 Dec
Corte Francigena

Townhouse in Pienza

PienzaLettings Suites
10.0 out of 10, Exceptional, (1)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is AU$148
includes taxes & fees
11 Jan - 12 Jan 2026
PienzaLettings Suites
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 Montisi Hotel Reviews

Find out more about Montisi

Everything you need to know about Montisi 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 Montisi 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 Montisi holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Montisi holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montisi. 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 Montisi 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 Montisi holiday rentals we have selected for you start as low as AU$114 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Montisi rentals

At Expedia, we put the best Montisi 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 Montisi 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 Montisi 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 Montisi. 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

Can I find a holiday rental in Montisi?

Yes, there are holiday rentals close to the most popular sights in Montisi, or you can select a more secluded option if you're looking for a relaxing stay.

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

Borgo Argiano: This holiday home rental outside of Montisi is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. You can relax into your holiday with a garden and a library.

What’s there to see and do in Montisi?

While exploring the area, visit family-friendly sights like Siena Circuit, or get outside and enjoy nature at Val di Chiana. In the wider area, you’ll find Monte Oliveto Maggiore Abbey and Historic Centre of Pienza.

What’s a holiday rental in Montisi like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montisi. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.