Rolling hills, a winding road, and scattered trees.

Montaione Holiday Rentals

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Our top choices for Montaione holiday rentals

1. Toscana Vacanze

Toscana Vacanze
MONTAIONE
The price is NZ$471
includes taxes & fees
2 Nov - 3 Nov
Toscana Vacanze

2. 2bed, 1bath Garden apt in Chianti!

2bed, 1bath Garden apt in Chianti!
Frazione Mura, Montaione
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful time staying at the house. The location is beautiful and peaceful, surrounded by nature and the house itself is charming and well cared for. The swimming pool and the tennis court were fantastic and made our stay even more enjoyable. It was the perfect place to relax and enjoy the Tuscan atmosphere. We truly enjoyed our stay and would love to return one day"
Germany
Cayit A.
The price is NZ$357
includes taxes & fees
7 Oct - 8 Oct
2bed, 1bath Garden apt in Chianti!

3. 2-BR 1 bath abode in the Chianti hills!

2-BR 1 bath abode in the Chianti hills!
Mura, Montaione
8.0 out of 10, Very good, (1 review)
"Check in Vorgang schwierig, da Gastgeber vergessen hat, dass wir kommen. Dann aber hat alles gut geklappt.Die Wohnung ist sehr renovierungsbedürftig, mein Mann hat erstmal die Klospülung repariert. Sonst hat sie ihren Charme und ist gut ausgestattet Gewürzen und anderen LebensmittelnToll gelegen mit Pool und Tennisplatz"
Germany
Anke G.
The price is NZ$357
includes taxes & fees
1 Nov - 2 Nov
2-BR 1 bath abode in the Chianti hills!

4. Donatello Apartment: Relaxation and Comfort in Montaione

Donatello Apartment: Relaxation and Comfort in Montaione
Montaione
The price is NZ$2,194
includes taxes & fees
4 Oct - 5 Oct
Donatello Apartment: Relaxation and Comfort in Montaione

5. Villetta Leonardo: Independence, Garden & Relaxation in Tuscany

Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Montaione
The price is NZ$2,261
includes taxes & fees
4 Oct - 5 Oct
Villetta Leonardo: Independence, Garden & Relaxation in Tuscany

6. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Villetta Brunelleschi: Privacy and Comfort on Two Levels
Montaione
The price is NZ$2,313
includes taxes & fees
4 Oct - 5 Oct
Villetta Brunelleschi: Privacy and Comfort on Two Levels

7. Michelangelo Apartment: Panoramic Views & Spacious Comfort

Michelangelo Apartment: Panoramic Views & Spacious Comfort
Montaione
The price is NZ$2,310
includes taxes & fees
4 Oct - 5 Oct
Michelangelo Apartment: Panoramic Views & Spacious Comfort

8. Botticelli Apartment – Spacious Comfort for Families and Groups

Botticelli Apartment – Spacious Comfort for Families and Groups
Montaione
The price is NZ$3,640
includes taxes & fees
5 Oct - 6 Oct
Botticelli Apartment – Spacious Comfort for Families and Groups

9. Giotto Apartment: Comfort and Relaxation in Montaione

Giotto Apartment: Comfort and Relaxation in Montaione
Montaione
The price is NZ$3,562
includes taxes & fees
5 Oct - 6 Oct
Giotto Apartment: Comfort and Relaxation in Montaione

10. Apartment Raffaello: Comfort and Relaxation with Private Outdoor Space

Apartment Raffaello: Comfort and Relaxation with Private Outdoor Space
Montaione
The price is NZ$3,599
includes taxes & fees
5 Oct - 6 Oct
Apartment Raffaello: Comfort and Relaxation with Private Outdoor Space

11. Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (37 reviews)
"Great place, difficult driving access but enjoyable"
United States
Sergio
The price is NZ$197
includes taxes & fees
1 Nov - 2 Nov
Tenuta Sant'Ilario

12. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
"Fantastic all around experience. The rooms were beautiful and clean and this unique mix of rustic modern Italian styling. Located right in the heart of the old city made it very easy to walk everywhere. The service was fantastic, I was able to message the team and within a minute I got the help and had my questions answered. I’d definitely stay there again."
Canada
Bradley
The price is NZ$217
includes taxes & fees
3 Nov - 4 Nov
Materia Rooms San Gimignano

13. Antica Dimora Leones

Antica Dimora Leones
Palaia
9.2 out of 10, Wonderful, (18 reviews)
"What a truly special place to stay in Tuscany. Zamira was a wonderful and kind hostess, and we couldn’t have asked for more. Breathtaking views from the hotel, delicious breakfast, and some great restaurants in walking distance. Would 100% go back and would highly recommend it to fellow travellers"
United Kingdom
Thomas
The price is NZ$125
includes taxes & fees
11 Oct - 12 Oct
Antica Dimora Leones

14. Borgo Antico Residence

Borgo Antico Residence
Certaldo Alto
10.0 out of 10, Exceptional, (3 reviews)
"Great place to relax take in the local culture and enjoy Tuscany."
United States
jane
The price is NZ$182
includes taxes & fees
11 Oct - 12 Oct
Borgo Antico Residence

15. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is NZ$267
includes taxes & fees
8 Oct - 9 Oct
Palazzo al Torrione 2

16. DomuS Miniato

DomuS Miniato
San Miniato
10.0 out of 10, Exceptional, (3 reviews)
"Klein aber fein. Sehr gepflegt und geschmackvoll eingerichtet mit Liebe zum Detail. Herrliche Aussicht vom kleinen Balkon. Nur die Parkplatzsuche war am späten Freitag Abend schwierig, weil gefühlt die halbe Jugend der Toscana nach San Miniato in den Ausgang geht."
United States
Thomas
The price is NZ$191
includes taxes & fees
25 Oct - 26 Oct
DomuS Miniato

17. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (13 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
The price is NZ$187
includes taxes & fees
2 Nov - 3 Nov
Casa Vacanze Le Case

18. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
San Gimignano City Centre
9.8 out of 10, Exceptional, (42 reviews)
"Authentic 13th century building with so much character and charm. The room was very unique and opened to a lovely courtyard. The location was great, and very close to the gate. A full Italian breakfast buffet was offered at a reasonable cost. Laundry service was also available. And the hosts were very friendly and helpful."
United States
Marilyn H.
The price is NZ$327
includes taxes & fees
10 Oct - 11 Oct
San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

19. Borgo San Giusto

Borgo San Giusto
Empoli
9.4 out of 10, Exceptional, (46 reviews)
"A lovely overnight stay here! Staff were so accommodating to our limited Italian and the children. Would recommend"
United Kingdom
Lucy
The price is NZ$201
includes taxes & fees
1 Nov - 2 Nov
Borgo San Giusto

20. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (65 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is NZ$246
includes taxes & fees
3 Nov - 4 Nov
B&B Palazzo Tortoli
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 Montaione Hotel Reviews

Find out more about Montaione

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Montaione holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Montaione. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Montaione. Seeing all the best attractions is bound to make you fall in love with Montaione. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Montaione short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Montaione?

Yes, there are holiday rentals close to the most popular sights in Montaione, or you can select a more secluded option if you're looking for a relaxing stay. Montaione is known for its wineries and golf courses. Make sure you have time to check out the spas and seafood restaurants during your trip.

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

Calanchi Apartments: This highly rated holiday home rental in Montaione offers an outdoor pool, a rooftop terrace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Montaione?

With 49 Expedia holiday rentals, you're guaranteed to find just the right place for your Montaione stay.

What’s there to see and do in Montaione?

Explore the area and family-friendly sights such as Chianti Observatory, or get out into nature at a spot like Sentierelsa Trail. Monastery of San Vivaldo and Castelfalfi Golf Course are a couple of places you'll find in the wider area.

What’s a holiday rental in Montaione like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montaione. Holiday rentals feature extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family gatherings.