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Piana Vacation Rentals

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Our top choices for Piana vacation rentals

1. 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 $158
CA $180 total
includes taxes & fees
Nov 14 - Nov 15
Casale dell'Assiolo

2. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is CA $213
CA $241 total
includes taxes & fees
Nov 26 - Nov 27
La Locanda di San Francesco

3. La Piccola Locanda

La Piccola Locanda
Chiusi
8.0 out of 10, Very good, (14 reviews)
"Very homey and wonderful people! We loved the restaurant below."
United States
autumn
The price is CA $168
CA $188 total
includes taxes & fees
Nov 12 - Nov 13
La Piccola Locanda

4. 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 $117
CA $152 total
includes taxes & fees
Nov 12 - Nov 13
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

5. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (75 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is CA $147
CA $202 total
includes taxes & fees
Nov 12 - Nov 13
Affitacamere Maria Gabriella

6. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (122 reviews)
"The room was beautifully designed, clean and fresh with stunning views in a truly historic building. Family run and a special experience!!"
United States
Slimane
The price is CA $196
CA $222 total
includes taxes & fees
Nov 24 - Nov 25
Meublé Il Riccio

7. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
The price is CA $92
CA $106 total
includes taxes & fees
Nov 26 - Nov 27
Abbadia Sicille Relais

8. La Locanda Di Cetona

La Locanda Di Cetona
Cetona
9.0 out of 10, Wonderful, (9 reviews)
"It was such a lovely experience. Bang in the centre of the town, still very quiet. The room was breathtaking, lovely breakfast (generosity though depended on staff). Overall such a great experience I would go back today!"
United Kingdom
GianPaolo
The price is CA $193
CA $212 total
includes taxes & fees
Dec 12 - Dec 13
La Locanda Di Cetona

9. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (145 reviews)
"We really enjoyed the room. Comfortable bed. Great location."
United States
Melissa
The price is CA $134
CA $154 total
includes taxes & fees
Nov 12 - Nov 13
Bed & Breakfast Vicolo dell'Oste

10. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (117 reviews)
"Was a very nice spot"
Canada
Andrew
The price is CA $111
CA $129 total
includes taxes & fees
Nov 12 - Nov 13
Residenza Fabroni

11. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is CA $170
CA $193 total
includes taxes & fees
Nov 12 - Nov 13
montorio

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 $114
CA $132 total
includes taxes & fees
Nov 15 - Nov 16
Artisti del Cavallo Tourism

13. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (50 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is CA $242
CA $272 total
includes taxes & fees
Nov 12 - Nov 13
Delcorto Suites

14. Boutique Apartment Eleganza

Boutique Apartment Eleganza
Chiusi Scalo
9.6 out of 10, Exceptional, (5 reviews)
"Amazing apartment!So close to the train!"
United States
Ryan W.
The price is CA $117
CA $143 total
includes taxes & fees
Nov 12 - Nov 13
Boutique Apartment Eleganza

15. 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 $148
CA $154 total
includes taxes & fees
Nov 12 - Nov 13
City / Village Apartment in Cortona with 1 bedrooms sleeps 2

16. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (171 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is CA $194
CA $223 total
includes taxes & fees
Nov 16 - Nov 17
Hotel San Gregorio

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 $100
CA $117 total
includes taxes & fees
Nov 12 - Nov 13
Vacation home with a panoramic terrace, ideal for families and couples

18. Boutique Apartment Natura

Boutique Apartment Natura
Chiusi
10.0 out of 10, Exceptional, (1 review)
"Great location and very clean!"
Canada
Shelley
The price is CA $114
CA $139 total
includes taxes & fees
Nov 16 - Nov 17
Boutique Apartment Natura

19. La Perla on Lake Trasimeno: Relaxation and Nature.

La Perla on Lake Trasimeno: Relaxation and Nature.
San Feliciano
The price is CA $157
CA $174 total
includes taxes & fees
Nov 12 - Nov 13
La Perla on Lake Trasimeno: Relaxation and Nature.

20. 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 $125
CA $143 total
includes taxes & fees
Nov 12 - Nov 13
Montecchio di Cortona
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 Piana Hotel Reviews

Find out more about Piana

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 Piana. 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

Can I find vacation rentals in Piana?

Yes, we have vacation rentals near popular points of interest in Piana, or you can select a more remote option if you're looking for a relaxing stay.

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

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome: Visitors like this Piana vacation home rental. It is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

What’s there to see and do in Piana?

Explore the area and family-friendly sights such as Tavernelle Aquatic Park, or get out into nature at a spot like Lake Trasimeno. Isola Maggiore and Chiusi Lake are a couple of places you'll find in the larger area.

What’s a vacation rental in Piana like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Piana. Vacation rentals feature extras like laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for families.