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Montisi 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 Montisi vacation rentals

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
Terrace/patio
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 ￥12,314
￥14,099 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Abbadia Sicille Relais
Exterior
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
Premium bedding, down comforters, pillowtop beds, minibar
Tuscasì Aparthotel

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (25)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ￥12,024
￥15,628 total
includes taxes & fees
Dec 25 - Dec 26
Tuscasì Aparthotel
Studio | Terrace/patio
La Dimora di Dida

La Dimora di Dida

La Dimora di Dida
Seggiano
The price is ￥11,586
￥12,745 total
includes taxes & fees
Dec 23 - Dec 24
La Dimora di Dida
Exterior
Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16)
"Great host, lovely place near Siena"
United Kingdom
Prem
Il Pozzo di Sant'Andrea
Property entrance
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 ￥13,782
￥15,899 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Residenza Fabroni
Panoramic Cottage, 1 Bedroom | Exterior
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
Triple Room, Balcony, City View | Desk, iron/ironing board, free WiFi, bed sheets
Al Mercato B&B

Al Mercato B&B

Al Mercato B&B
Siena City Centre
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 ￥11,587
￥15,111 total
includes taxes & fees
Dec 24 - Dec 25
Al Mercato B&B
Interior
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
Monolocale Exclusive, vista città, secondo piano senza ascensore | 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 ￥14,932
￥17,164 total
includes taxes & fees
Jan 6 - Jan 7, 2026
TuscanyLettings Studio&Room
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub
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
Exterior
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
Interior detail
La Coroncina Lodging

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (42)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is ￥14,499
￥16,688 total
includes taxes & fees
Dec 22 - Dec 23
La Coroncina Lodging
Property grounds
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Montalcino
The price is ￥1,099,078
￥1,191,437 total
includes taxes & fees
Dec 22 - Dec 23
VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24
Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio
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 ￥12,377
￥14,354 total
includes taxes & fees
Dec 22 - Dec 23
PienzaLettings Suites
Exterior
Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
The price is ￥13,602
￥15,701 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Casa Gioia - Casa Olivieri
Massages
Chalet Il Cristallo

Chalet Il Cristallo

Chalet Il Cristallo
Castel del Piano
6.8 out of 10, (3)
"Puzza di chiuso e muffa in camera, muffa sul muro, letto con trapunta, lenzuolo e coprimaterasso con n macchia di non so cosa, per aprire lucernario del bagno ho dovuto togliere ragnatele con insetti incorporati. Molle del letto che si sentivano nella schiena e per finire nido sul davanzale che impediva la chiusura degli antoni, non avrei mai fatto togliere il nido amo gli animali, ma le tende interne oltre che sporche non si potevano tirare per impedire un po' alla luce di entrare, alle ore 5...
Italy
Giordano
The price is ￥10,050
￥11,609 total
includes taxes & fees
Jan 21 - Jan 22, 2026
Chalet Il Cristallo
Standard Double Room | Bathroom | Deep soaking tub, rainfall showerhead, free toiletries, hair dryer
Piazza Paradiso Accomodation

Piazza Paradiso Accomodation

Piazza Paradiso Accomodation
Siena City Centre
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
Food court
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 ￥27,366
￥30,841 total
includes taxes & fees
Jan 18 - Jan 19, 2026
La Locanda di San Francesco
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Everything was perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!"
Sabrina 4-night trip
Posted 3 days ago
Monastero di Cortona Hotel & Spa

Find out more about Montisi

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

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Frequently asked questions

Can I find a vacation rental in Montisi?

Yes, we give you a choice of vacation rentals close to well known sights in Montisi, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation rentals in Montisi?

Borgo Argiano: This vacation home near Montisi is located on a river and has a balcony, a terrace, and a barbecue grill 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 vacation 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 larger area, you’ll find Monte Oliveto Maggiore Abbey and Historic Centre of Pienza.

What’s a vacation rental in Montisi like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Montisi. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.