Monteriggioni Holiday Rentals

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Our top choices for Monteriggioni holiday rentals

Holiday Home in Toscana

LOVE NEST SIENA YOUR LOVE NEST
The price is NZ$262
includes taxes & fees
6 Jan - 7 Jan 2026
LOVE NEST SIENA YOUR LOVE NEST
10.0 out of 10, Exceptional, (12)
"Monteriggioni is the perfect location between Siena, San Gimignani, and roads to Chianti. The hosts Marcela, Enzo, and Alessandro really made us feel at home and comfortable. The property is beautiful, quiet, with unforgettable sunsets! Time at the pool is refreshing and relaxing, with beautiful views of the surrounding countryside. The authentic Italian kitchen was perfect for creating your own breakfasts and dinners. The bathrooms with showers have all you need, and the beds are really...
United States
Daniel D.
The price is NZ$697
includes taxes & fees
27 Dec - 28 Dec
Pleasant characteristic hayloft that has been renovated into holiday apartment in a part of the Chianti that is ideal for visiting the most important towns.
10.0 out of 10, Exceptional, (1)
"We absolutely loved Marcella & Enzo’s property. The pool was exactly what we needed to relax after a busy and hot few days in Rome & Venice. Just a 10 min drive from the train station. The home is set up very nicely with the 2 bedrooms and 2 bathrooms. We loved meeting the donkeys, having a quiet place to relax along with modern conveniences like a washing machine. We were treated like family. We hope to return in the future. Huge thank you! Breathtaking views. The cottage was picture perfect. "
United States
Anonymous traveller
The price is NZ$861
includes taxes & fees
7 Jan - 8 Jan 2026
APART. OF CHARM, AIR CONDITIONING, FENCED POOL IN THE HEART OF CHIANTI-FLORENCE
10.0 out of 10, Exceptional, (66)
"Great Place and super nice Host. Location is very nice, top equiped and located only a couple of minutes away from Siena. Host is a really nice Person that has super good ideas where to go, in turism and wine/food matters. Really loved our stay (me and my Kids 14years), definitely come back. Highly recommended"
Germany
Michael G.
The price is NZ$491
includes taxes & fees
29 Dec - 30 Dec
La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

Apartment in Monteriggioni

--- CASA DEL FATTORE ---
The price is NZ$832
includes taxes & fees
27 Dec - 28 Dec
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Apartment in Monteriggioni

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The price is NZ$894
includes taxes & fees
8 Jan - 9 Jan 2026
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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 NZ$175
includes taxes & fees
20 Jan - 21 Jan 2026
Al Mercato B&B

Townhouse in Colle di Val d'Elsa

Sportland
7.2 out of 10, Good, (5)
"Struttura essenziale ed economica "
Italy
Giorgio
Sportland

Townhouse in Sovicille

Casa di Campagna in Toscana
9.4 out of 10, Exceptional, (19)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
Casa di Campagna in Toscana

Aparthotel in Sovicille

Tuscasì Aparthotel
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 NZ$171
includes taxes & fees
5 Jan - 6 Jan 2026
Tuscasì Aparthotel

Townhouse in Ravacciano

Domus il Palio B&B
9.2 out of 10, Wonderful, (81)
"Convenient for parking, clean and relatively easy access to the town. The rooms were functional, getting into the place after hours was easy ( check in). No breakfast but a supermarket was 300 meters away"
Canada
Marcus
Domus il Palio B&B

Townhouse in San Gimignano City Centre

Palazzo al Torrione 2
9.2 out of 10, Wonderful, (107)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is NZ$239
includes taxes & fees
19 Jan - 20 Jan 2026
Palazzo al Torrione 2

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 Siena City Centre

Siena Vip
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
The price is NZ$273
includes taxes & fees
4 Jan - 5 Jan 2026
Siena Vip

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

Townhouse in Gambassi Terme

Tenuta Sant'Ilario
9.4 out of 10, Exceptional, (33)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario

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

Townhouse in Gaiole in Chianti

L' Eroico
10.0 out of 10, Exceptional, (12)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico

Cottage in Siena

Fullino Nero
9.6 out of 10, Exceptional, (49)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is NZ$208
includes taxes & fees
7 Jan - 8 Jan 2026
Fullino Nero

Townhouse in Petriccio

Villa le Camelie Siena
8.6 out of 10, Excellent, (8)
"Personal people are very good. "
Switzerland
Wenjuan
The price is NZ$181
includes taxes & fees
27 Dec - 28 Dec
Villa le Camelie Siena
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 Monteriggioni Hotel Reviews

Find out more about Monteriggioni

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

Monteriggioni holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Monteriggioni. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Monteriggioni 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 Monteriggioni holiday rentals we have selected for you start as low as NZ$118 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Monteriggioni rentals

At Expedia, we put the best Monteriggioni 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 Monteriggioni 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 Monteriggioni 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 Monteriggioni. 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 Monteriggioni?

Yes, there are holiday rentals close to the most popular sights in Monteriggioni, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Monteriggioni speak positively about the countryside and wineries in this destination. Make sure you have time to check out the local tours and churches during your trip.

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

Borgo Argiano: This holiday home rental outside Monteriggioni 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.

How many holiday rentals are there in Monteriggioni?

Choose from 17 Expedia holiday rentals in Monteriggioni for a memorable holiday.

What’s there to see and do in Monteriggioni?

Val di Merse and Alta Val d'Elsa River Park are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Monteriggioni Castle and San Leonardo al Lago.

What’s a holiday rental in Monteriggioni like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Monteriggioni. Holiday rentals feature amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for families.