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Check prices for these dates

Tonight
15 Dec - 16 Dec
Tomorrow
16 Dec - 17 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Montisi holiday rentals

Food and drink
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 ฿6,513
฿7,387 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio
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 ฿2,303
฿2,644 total
includes taxes & fees
18 Dec - 19 Dec
Abbadia Sicille Relais
Premium bedding, down duvets, pillow-top 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 ฿2,086
฿2,777 total
includes taxes & fees
20 Dec - 21 Dec
Tuscasì Aparthotel
1 treatment room, massages
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
The price is ฿7,273
฿8,148 total
includes taxes & fees
26 Dec - 27 Dec
Casanova - Panoramic Rooms and Suites
Daily continental breakfast (EUR 20 per person)
Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is ฿6,061
฿6,815 total
includes taxes & fees
6 Jan - 7 Jan 2026
Residenza d'Epoca Palazzo Borghesi
City view
Regis Condo

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
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 ฿3,148
฿3,611 total
includes taxes & fees
11 Jan - 12 Jan 2026
Bellarmino Boutique Apartments
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 ฿2,827
฿3,258 total
includes taxes & fees
16 Dec - 17 Dec
Residenza Fabroni
Deluxe Apartment | Premium bedding, down duvets, in-room safe, desk
Borgo Argiano

Borgo Argiano

Borgo Argiano
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (73)
"Very comfortable stay. "
United States
Victor
Borgo Argiano
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 ฿8,364
฿9,348 total
includes taxes & fees
16 Dec - 17 Dec
Il Tosco
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming 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 ฿2,860
฿3,294 total
includes taxes & fees
16 Dec - 17 Dec
La Coroncina Lodging
Aerial view
Bosco della Spina

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (169)
"Views are amazing. Staff are very pleasant and helpful. "
Canada
Maureen
Bosco della Spina
24-inch flat-screen TV with digital channels, TV
Palazzo Lenzi

Palazzo Lenzi

Palazzo Lenzi
Siena City Centre
9.0 out of 10, Wonderful, (2)
"Very very nice. Enjoyed our stay. Air conditioning did not work well so a bit hot. But overall very nice. "
United States
Daniel
The price is ฿7,323
฿8,204 total
includes taxes & fees
16 Dec - 17 Dec
Palazzo Lenzi
Balcony
Osteria del Borgo

Osteria del Borgo

Osteria del Borgo
Montepulciano
9.0 out of 10, Wonderful, (156)
"Staff and location were both excellent."
United States
Nicholas
Osteria del Borgo
Front of property
Podere La Chiusella

Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.4 out of 10, Exceptional, (30)
"Et sjarmerende lite B&B. Har nok vært utrolig vakkert i sine glansdager, men områdene rundt bærer preg av lite vedlikehold. Leiligheten var helt grei for en overnatting. Gulvet på badet var ikke rent. Når vi tørket opp etter oss ble håndkleet møkkete. Men overnattingen var helt grei alt i alt. Når vi skulle sjekke ut var det ikke et menneske å se, resepsjonen var stengt. Endte med å sette nøklene i døra og dra da alt var betalt ved bestilling."
Norway
Elisabeth
Podere La Chiusella
City Apartment, 3 Bedrooms | City view
Palazzo Piccolomini

Palazzo Piccolomini

Palazzo Piccolomini
Siena City Centre
6.0 out of 10, (1)
"Großzügige Unterkunft, tolle Lage, leider aber lieblos gestaltet. Türgriffe defekt, Beleuchtung (Helligkeit) naja, Badewanne mit Duschvorhang (geeignet für die Produktion eines Badesees :/ )….. aber im Großen und Ganzen ok"
Germany
Frank
The price is ฿5,758
฿6,481 total
includes taxes & fees
16 Dec - 17 Dec
Palazzo Piccolomini
Exterior
The Balcony Suite -Piazza del Campo View

The Balcony Suite -Piazza del Campo View

The Balcony Suite -Piazza del Campo View
Siena City Centre
9.2 out of 10, Wonderful, (16)
"Perfect location to explore Siena, right on the Campo. The apartment was warm and comfortable. As to be expected in such a central location, the noise & music from then restaurants on the piazza was loud till the early hours on Saturday night (so bring earplugs) but the other night was fine. "
Australia
Nicola
The price is ฿4,006
฿4,666 total
includes taxes & fees
16 Dec - 17 Dec
The Balcony Suite -Piazza del Campo View
Comfort Single Room, Shared Bathroom (Casato 35) | Exterior
Rinidia Siena Centro

Rinidia Siena Centro

Rinidia Siena Centro
Siena City Centre
8.0 out of 10, Very good, (1)
"The property is in a FANTASTIC location."
United States
Donna
The price is ฿5,030
฿5,681 total
includes taxes & fees
13 Jan - 14 Jan 2026
Rinidia Siena Centro
Terrace/patio
Antico Brunello

Antico Brunello

Antico Brunello
Montalcino
The price is ฿244,443
฿269,258 total
includes taxes & fees
16 Dec - 17 Dec
Antico Brunello
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

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano

10/10 Excellent
"The best in Siena."
David 1-night trip
Posted 2 days ago
Hotel Certosa Di Maggiano

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:

  • View our selection of featured holiday rentals in Montisi
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  • Enter your travel dates to view the best deals on holiday rentals in Montisi while they last

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

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 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.