Rolling hills, a winding road, and scattered trees.

Montaione Vacation Rentals

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Our top choices for Montaione vacation rentals

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 CA $112
CA $169 total
includes taxes & fees
Aug 3 - Aug 4
La Casina of Via Cresci, 14

Villetta Brunelleschi: Privacy and Comfort on Two Levels

Villetta Brunelleschi: Privacy and Comfort on Two Levels
Montaione
The price is CA $626
CA $784 total
includes taxes & fees
Aug 25 - Aug 26
Villetta Brunelleschi: Privacy and Comfort on Two Levels

Giotto Apartment: Comfort and Relaxation in Montaione

Giotto Apartment: Comfort and Relaxation in Montaione
Montaione
The price is CA $450
CA $607 total
includes taxes & fees
Aug 22 - Aug 23
Giotto Apartment: Comfort and Relaxation in Montaione

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 CA $202
CA $389 total
includes taxes & fees
Aug 6 - Aug 7
2bed, 1bath Garden apt in Chianti!

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 CA $225
CA $409 total
includes taxes & fees
Aug 8 - Aug 9
2-BR 1 bath abode in the Chianti hills!

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 CA $2,159
CA $2,680 total
includes taxes & fees
Aug 6 - Aug 7
Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

Villetta Leonardo: Independence, Garden & Relaxation in Tuscany

Villetta Leonardo: Independence, Garden & Relaxation in Tuscany
Montaione
The price is CA $514
CA $671 total
includes taxes & fees
Aug 28 - Aug 29
Villetta Leonardo: Independence, Garden & Relaxation in Tuscany

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 CA $228
CA $256 total
includes taxes & fees
Aug 2 - Aug 3
Tenuta Sant'Ilario

Borgo San Giusto

Borgo San Giusto
Empoli
9.4 out of 10, Exceptional, (42 reviews)
"Lovely location and excellent staff. Restaurant on site is amazing! "
United Kingdom
Paul
The price is CA $155
CA $176 total
includes taxes & fees
Jul 31 - Aug 1
Borgo San Giusto

Antica Dimora Leones

Antica Dimora Leones
Palaia
9.2 out of 10, Wonderful, (17 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 CA $102
CA $118 total
includes taxes & fees
Aug 2 - Aug 3
Antica Dimora Leones

Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (43 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is CA $162
CA $188 total
includes taxes & fees
Aug 23 - Aug 24
Villa San Filippo

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (84 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is CA $249
CA $282 total
includes taxes & fees
Jul 31 - Aug 1
Antico Borgo il Cardino

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 CA $172
CA $197 total
includes taxes & fees
Jul 31 - Aug 1
Casa Vacanze Le Case

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is CA $139
CA $156 total
includes taxes & fees
Jul 31 - Aug 1
Palazzo Pacini

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 CA $105
CA $116 total
includes taxes & fees
Aug 14 - Aug 15
Affittacamere e Ristorante Ariete

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 CA $222
CA $249 total
includes taxes & fees
Aug 12 - Aug 13
Tenuta Quadrifoglio

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (116 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is CA $127
CA $143 total
includes taxes & fees
Aug 6 - Aug 7
Chianti Village Morrocco

B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (64 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 CA $196
CA $224 total
includes taxes & fees
Jul 31 - Aug 1
B&B Palazzo Tortoli

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 CA $100
CA $155 total
includes taxes & fees
Jul 31 - Aug 1
Borgo Antico Residence

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location and beautiful room. Staff weren't that friendly but I think it would have been better if we spoke Italian."
Canada
Sophie
The price is CA $151
CA $214 total
includes taxes & fees
Aug 7 - Aug 8
Palazzo al Torrione 2
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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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. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Montaione?

With 43 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 Peccioli Prehistoric Park, or get out into nature at a spot like Casciana Thermal Baths. 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.