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Montanare Vacation Rentals

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Our top choices for Montanare vacation rentals

1. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (45 reviews)
"It was wonderful!"
United States
Wade
The price is CA $118
CA $140 total
includes taxes & fees
Nov 15 - Nov 16
iConic Wellness Resort

2. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
9.8 out of 10, Exceptional, (9 reviews)
"Nice property"
United States
Joseph
The price is CA $147
CA $153 total
includes taxes & fees
Nov 16 - Nov 17
City / Village Apartment in Cortona with 1 bedrooms sleeps 2

3. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is CA $290
CA $321 total
includes taxes & fees
Nov 15 - Nov 16
CASA AMBRA

4. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is CA $187
CA $213 total
includes taxes & fees
Nov 15 - Nov 16
San Michele al Borgo

5. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
9.0 out of 10, Wonderful, (2 reviews)
"Super søde værter. Og rigtig fint værelse. Vi kommer igen"
Denmark
Emma
The price is CA $151
CA $173 total
includes taxes & fees
Nov 20 - Nov 21
Casale dell'Assiolo

6. La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
9.8 out of 10, Exceptional, (39 reviews)
"we loved the rooms—especially"
United States
Jean V. A.
The price is CA $204
CA $294 total
includes taxes & fees
Dec 8 - Dec 9
La Finestra sul Teatro

7. Cortona Shabby Chic House<br>(Detached & Balcony)

Cortona Shabby Chic House<br>(Detached & Balcony)
Cortona Old Town
10.0 out of 10, Exceptional, (3 reviews)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is CA $194
CA $216 total
includes taxes & fees
Nov 15 - Nov 16
Cortona Shabby Chic House<br>(Detached & Balcony)

8. Cortonas Rooftop Nest

Cortonas Rooftop Nest
Cortona Old Town
10.0 out of 10, Exceptional, (12 reviews)
"Absolute gem of a property. Margherita is an excellent host as well!"
United States
Robin F.
The price is CA $211
CA $235 total
includes taxes & fees
Nov 28 - Nov 29
Cortonas Rooftop Nest

9. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi
Cortona
The price is CA $568
CA $633 total
includes taxes & fees
Dec 13 - Dec 14
Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

10. Montecchio di Cortona

Montecchio di Cortona
Montecchio
9.0 out of 10, Wonderful, (2 reviews)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is CA $124
CA $142 total
includes taxes & fees
Nov 17 - Nov 18
Montecchio di Cortona

11. Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi
Cortona
8.8 out of 10, Excellent, (3 reviews)
"Angelo was so friendly. He met us at the property and showed us around. The house is beautiful and peaceful. Thank you for a lovely stay."
United States
Bonnie B.
The price is CA $173
CA $179 total
includes taxes & fees
Nov 22 - Nov 23
Apartment "La Vecchia Fornace La Terrazza" with Shared Pool & Wi-Fi

12. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
The price is CA $113
CA $131 total
includes taxes & fees
Nov 15 - Nov 16
Artisti del Cavallo Tourism

13. Apartment 'Posta Del Lago' with Lake View, Private Terrace and Wi-Fi

Apartment 'Posta Del Lago' with Lake View, Private Terrace and Wi-Fi
Passignano sul Trasimeno
10.0 out of 10, Exceptional, (2 reviews)
"Eine ausgesprochen angenehme Wohnung, sehr geräumig, ansprechend und zugleich praktisch eingerichtet, sehr sauber, superfreundliche, aber zurückhaltende Vermieter. Ein Ort, an den wir gerne zurückkehren werden."
Germany
Tobias W.
The price is CA $299
CA $304 total
includes taxes & fees
Nov 15 - Nov 16
Apartment 'Posta Del Lago' with Lake View, Private Terrace and Wi-Fi

14. Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi
Cortona
10.0 out of 10, Exceptional, (1 review)
"Pros: il luogo che ci circondava rilassante ottimo. Cons: nulla come dicevo luogo ottimo."
Italy
Anonymous traveller
The price is CA $345
CA $411 total
includes taxes & fees
Nov 30 - Dec 1
Apartment 'L'Olivo Casa del Nonno Bingheri' with Shared Garden & Wi-Fi

15. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...
United Kingdom
Anna
The price is CA $116
CA $151 total
includes taxes & fees
Nov 19 - Nov 20
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

16. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is CA $138
CA $154 total
includes taxes & fees
Nov 20 - Nov 21
Vicolo Della Scala Rooms - La Luna

17. Vacation home with a panoramic terrace, ideal for families and couples

Vacation home with a panoramic terrace, ideal for families and couples
Cortona
The price is CA $99
CA $116 total
includes taxes & fees
Nov 15 - Nov 16
Vacation home with a panoramic terrace, ideal for families and couples

18. Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi

Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi
lisciano niccone
The price is CA $802
CA $805 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi

19. Home of the Sun

Home of the Sun
Passignano sul Trasimeno
10.0 out of 10, Exceptional, (2 reviews)
"Highly Recommend!I couldn’t have asked for a better place to stay! The property was absolutely spotless, beautifully maintained, and incredibly comfortable. You can tell that a lot of care and attention goes into making sure guests have a wonderful experience.The host was fantastic—warm, welcoming, attentive, and genuinely committed to making sure everything was perfect. Communication was excellent, and I felt right at home throughout my stay.The location was another huge plus! Centrally located...
United States
Randell P.
The price is CA $170
CA $176 total
includes taxes & fees
Nov 15 - Nov 16
Home of the Sun

20. Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom

Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
Lisciano Niccone
10.0 out of 10, Exceptional, (1 review)
"Pros: The Quietness of the wonderful mornings, in the middle of Tuscan Woods. The clean and big pool with a view. The host, very friendly and engaged. a perfect vacation!"
United States
Anonymous traveller
The price is CA $802
CA $805 total
includes taxes & fees
Nov 15 - Nov 16
Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
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 Montanare Hotel Reviews

Find out more about Montanare

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 Montanare. 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.

Frequently asked questions

Are there vacation rentals in Montanare?

Yes, we give you a choice of vacation rentals close to popular attractions in Montanare, or you can choose a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Montanare has to offer?

Villa Banditello, secluded, panoramic view over Montepulciano valley.: Visitors like this Montanare vacation home rental. It is located in a rural location and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the books in this rental home to help you unwind.

What’s there to see and do in Montanare?

Explore the area and family-friendly sights such as Naturalistic Oasis La Valle, or get out into nature at a spot like Isola Maggiore. In the larger area, you’ll find Villa Bramasole and Piazza della Repubblica.

What’s a vacation rental in Montanare like?

A vacation rental is a private property you can book for a long or short time in Montanare. Vacation rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for small groups.