Rolling hills, a winding road, and scattered trees.

Montaione Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Montaione vacation rentals

A kitchen with wooden cabinets, a dining table with chairs, and a hanging light fixture.

1. Toscana Vacanze

Toscana Vacanze
MONTAIONE
$219 nightly
The price is $244
Oct 30 - Oct 31
Total with taxes and fees
Toscana Vacanze
An outdoor brick barbecue area with a wooden bench nearby.

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.
$197 nightly
The price is $199
Oct 18 - Oct 19
Total with taxes and fees
2bed, 1bath Garden apt in Chianti!
A rectangular swimming pool with clear blue water, surrounded by a tiled deck.

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.
$197 nightly
The price is $199
Nov 2 - Nov 3
Total with taxes and fees
2-BR 1 bath abode in the Chianti hills!
A rural property with stone buildings, a garden, and a view of rolling hills.

4. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Villetta Brunelleschi: Privacy and Comfort on Two Levels
Montaione
$2,795 nightly
The price is $2,798
Oct 13 - Oct 14
Total with taxes and fees
Villetta Brunelleschi: Privacy and Comfort on Two Levels
A rural property with stone buildings, a garden, and a view of rolling hills.

5. Botticelli Apartment – Spacious Comfort for Families and Groups

Botticelli Apartment – Spacious Comfort for Families and Groups
Montaione
$2,795 nightly
The price is $2,798
Oct 13 - Oct 14
Total with taxes and fees
Botticelli Apartment – Spacious Comfort for Families and Groups
A rural property with stone buildings, a garden, and a view of rolling hills.

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

Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Montaione
$2,795 nightly
The price is $2,798
Oct 13 - Oct 14
Total with taxes and fees
Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
A rural property with stone buildings, a garden, and a view of rolling hills.

7. Michelangelo Apartment: Panoramic Views & Spacious Comfort

Michelangelo Apartment: Panoramic Views & Spacious Comfort
Montaione
$2,795 nightly
The price is $2,798
Oct 13 - Oct 14
Total with taxes and fees
Michelangelo Apartment: Panoramic Views & Spacious Comfort
A rural property with stone buildings, a garden, and a view of rolling hills.

8. Giotto Apartment: Comfort and Relaxation in Montaione

Giotto Apartment: Comfort and Relaxation in Montaione
Montaione
$2,795 nightly
The price is $2,798
Oct 13 - Oct 14
Total with taxes and fees
Giotto Apartment: Comfort and Relaxation in Montaione
A rural property with stone buildings, a garden, and a view of rolling hills.

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

Apartment Raffaello: Comfort and Relaxation with Private Outdoor Space
Montaione
$2,795 nightly
The price is $2,798
Oct 13 - Oct 14
Total with taxes and fees
Apartment Raffaello: Comfort and Relaxation with Private Outdoor Space
A rural property with stone buildings, a garden, and a view of rolling hills.

10. Donatello Apartment: Relaxation and Comfort in Montaione

Donatello Apartment: Relaxation and Comfort in Montaione
Montaione
$2,795 nightly
The price is $2,798
Oct 13 - Oct 14
Total with taxes and fees
Donatello Apartment: Relaxation and Comfort in Montaione
A stone-walled room with a wooden desk, a chair, a TV, and a large window with curtains.

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
$97 nightly
The price is $110
Nov 12 - Nov 13
Total with taxes and fees
Tenuta Sant'Ilario
A courtyard with brick flooring, outdoor tables with umbrellas, and a brick fountain.

12. 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
$89 nightly
The price is $102
Oct 22 - Oct 23
Total with taxes and fees
Borgo Antico Residence
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

13. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
$92 nightly
The price is $107
Nov 2 - Nov 3
Total with taxes and fees
Casa Vacanze Le Case
A rustic outdoor seating area with a table and chairs, a wooden door, and a view of a mountain range.

14. Coppo – Apartment with Pool and Views of the Tuscan Hills

Coppo – Apartment with Pool and Views of the Tuscan Hills
Gambassi Terme
$414 nightly
The price is $417
Oct 14 - Oct 15
Total with taxes and fees
Coppo – Apartment with Pool and Views of the Tuscan Hills
An open wooden door leading to an outdoor patio with a table and chairs.

15. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 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
$117 nightly
The price is $134
Nov 8 - Nov 9
Total with taxes and fees
Palazzo al Torrione 2
A bedroom with a large bed, two ottomans, a chandelier, and a view through an arched doorway to a dining area.

16. 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
$99 nightly
The price is $112
Nov 1 - Nov 2
Total with taxes and fees
Borgo San Giusto
A garden with a round table and wicker chairs under a tree.

17. Antica Dimora Leones

Antica Dimora Leones
Palaia
9.2 out of 10, Wonderful, (19 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
$57 nightly
The price is $67
Oct 19 - Oct 20
Total with taxes and fees
Antica Dimora Leones
A view from a window overlooking a rural landscape with fields and a distant mountain range.

18. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (66 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
$128 nightly
The price is $147
Oct 18 - Oct 19
Total with taxes and fees
B&B Palazzo Tortoli
A narrow street with stone buildings, a tower, and an archway.

19. 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
$105 nightly
The price is $122
Nov 4 - Nov 5
Total with taxes and fees
Materia Rooms San Gimignano
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

20. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.4 out of 10, Exceptional, (270 reviews)
"Very friendly and clean."
United States
Mohamed
$138 nightly
The price is $155
Nov 8 - Nov 9
Total with taxes and fees
Relais Villa Olmo - Place of Charme
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

Castelfalfi

Castelfalfi

10/10 Excellent
"Beautiful place to stay!"
Peter 3-night trip
Posted 1 day ago
Castelfalfi

Find out more about Montaione

Everything you need to know about Montaione vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montaione vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Montaione vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montaione vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montaione. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Montaione in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montaione rentals

At Expedia, we put the best Montaione vacation 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 Montaione 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 Montaione vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montaione. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Montaione?

Yes, we give you a choice of vacation rentals close to popular points of interest in Montaione, or you can go with a more remote 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 vacation rentals that Montaione has to offer?

Calanchi Apartments: Visitors give good reviews to this Montaione vacation home rental, which offers an outdoor pool, a rooftop terrace, and a barbecue grill 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 vacation with a garden and a selection of games.

How many vacation rentals are there in Montaione?

With 49 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Montaione like?

Vacation rentals are privately owned properties you can book for short or long periods in Montaione. Vacation rentals feature extras such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family getaway.