Rolling hills, a winding road, and scattered trees.

Montaione Holiday Rentals

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Our top choices for Montaione holiday rentals

1. La Casina of Via Cresci, 14

La Casina of Via Cresci, 14
Montaione
10.0 out of 10, Exceptional, (4 reviews)
"Cute villa- exactly as described. "
United States
Jo P.
The price is NZ$206
includes taxes & fees
19 Aug - 20 Aug
La Casina of Via Cresci, 14

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$381
includes taxes & fees
15 Sept - 16 Sept
2bed, 1bath Garden apt in Chianti!

3. Giotto Apartment: Comfort and Relaxation in Montaione

Giotto Apartment: Comfort and Relaxation in Montaione
Montaione
The price is NZ$503
includes taxes & fees
1 Sept - 2 Sept
Giotto Apartment: Comfort and Relaxation in Montaione

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

Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Montaione
The price is NZ$694
includes taxes & fees
28 Aug - 29 Aug
Villetta Leonardo: Independence, Garden & Relaxation in Tuscany

5. Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi
San Vivaldo
The price is NZ$3,264
includes taxes & fees
19 Aug - 20 Aug
Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

6. Donatello Apartment: Relaxation and Comfort in Montaione

Donatello Apartment: Relaxation and Comfort in Montaione
Montaione
The price is NZ$575
includes taxes & fees
3 Sept - 4 Sept
Donatello Apartment: Relaxation and Comfort in Montaione

7. Botticelli Apartment – Spacious Comfort for Families and Groups

Botticelli Apartment – Spacious Comfort for Families and Groups
Montaione
The price is NZ$647
includes taxes & fees
3 Sept - 4 Sept
Botticelli Apartment – Spacious Comfort for Families and Groups

8. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Villetta Brunelleschi: Privacy and Comfort on Two Levels
Montaione
The price is NZ$804
includes taxes & fees
25 Aug - 26 Aug
Villetta Brunelleschi: Privacy and Comfort on Two Levels

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

Apartment Raffaello: Comfort and Relaxation with Private Outdoor Space
Montaione
The price is NZ$767
includes taxes & fees
3 Sept - 4 Sept
Apartment Raffaello: Comfort and Relaxation with Private Outdoor Space

10. 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$272
includes taxes & fees
6 Sept - 7 Sept
Tenuta Sant'Ilario

11. Antica Dimora Leones

Antica Dimora Leones
Palaia
9.2 out of 10, Wonderful, (18 reviews)
"Wonderful and unique place to stay. Staff were terrific. The church bells ring through the night so bring earplugs if you’re a light sleeper!"
Canada
Brendan
The price is NZ$146
includes taxes & fees
16 Sept - 17 Sept
Antica Dimora Leones

12. Tenuta Quadrifoglio

Tenuta Quadrifoglio
Gambassi Terme
10.0 out of 10, Exceptional, (5 reviews)
"A lovely spot for relaxation .The appartments were lovely and comfortable .the only criticism was you do need a car to get any where. It is totally in the middle of nowhere. "
United Kingdom
Geraldine
The price is NZ$282
includes taxes & fees
7 Sept - 8 Sept
Tenuta Quadrifoglio

13. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (11 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is NZ$250
includes taxes & fees
28 Aug - 29 Aug
Casa Vacanze Le Case

14. DomuS Miniato

DomuS Miniato
San Miniato
10.0 out of 10, Exceptional, (2 reviews)
"Super clean, felt brand new with a beaaautiful view on the terrace! Quite a few stairs (heavy luggage :D) but definitely worth it! Sadly we only stayed two nights"
United Kingdom
Celesta
The price is NZ$208
includes taxes & fees
2 Sept - 3 Sept
DomuS Miniato

15. Borgo San Giusto

Borgo San Giusto
Empoli
9.4 out of 10, Exceptional, (43 reviews)
"Lovely location and excellent staff. Restaurant on site is amazing! "
United Kingdom
Paul
The price is NZ$232
includes taxes & fees
26 Aug - 27 Aug
Borgo San Giusto

16. Affittacamere e Ristorante Ariete

Affittacamere e Ristorante Ariete
Ponsacco
8.8 out of 10, Excellent, (3 reviews)
"This place is a bit further out from Pisa, but we still had a really nice stay and made the most of it. It’s great value for money, which was a big plus. The hotel itself is a little old-fashioned, but honestly, the staff more than made up for it—they were super friendly and welcoming the whole time. The restaurant was also a highlight, with really tasty food that we enjoyed a lot. It’s a good spot if you’ve got a car and want to explore the nearby villages and surrounding area."
United Kingdom
Martina
The price is NZ$123
includes taxes & fees
22 Aug - 23 Aug
Affittacamere e Ristorante Ariete

17. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (111 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is NZ$261
includes taxes & fees
21 Aug - 22 Aug
Palazzo al Torrione 2

18. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
The price is NZ$218
includes taxes & fees
1 Sept - 2 Sept
Materia Rooms San Gimignano

19. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (48 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is NZ$194
includes taxes & fees
17 Sept - 18 Sept
Villa San Filippo

20. Affittacamere a 20 minuti da Firenze

Affittacamere a 20 minuti da Firenze
Empoli
8.2 out of 10, Very good, (24 reviews)
"Great location between Florence and Pisa. Also only a 5 minute walk to the train station that will take you to both cities. Great place to stay if looking for something quite and away from the crowds."
United States
Joshua
The price is NZ$137
includes taxes & fees
23 Aug - 24 Aug
Affittacamere a 20 minuti da Firenze
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. Make the most of garden in this rental home to help you unwind.

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 Tenuta San Vito, or get out into nature at a spot like Sentierelsa Trail. Castelfalfi Golf Course and Monastery of San Vivaldo 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.