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Calzolaro Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Calzolaro vacation rentals

A stone building with a balcony and a small garden area with plants.

1. L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is ￥9,535
￥10,489 total
includes taxes & fees
Oct 29 - Oct 30
L'Antica Sosta
Pool

2. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (41 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is ￥11,779
￥14,023 total
includes taxes & fees
Nov 16 - Nov 17
iConic Wellness Resort
A cozy living room with a wooden ceiling, a sofa, a dining table with chairs, a bookshelf, and a view through a window.

3. La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!

La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!
Castel Rigone
10.0 out of 10, Exceptional, (4 reviews)
"The place was amazing and as advertised! We enjoyed the area very much, the views are amazing! We shopped at the local market and enjoyed dinner in both nights we were there. If we are back in the area, we will stay here again! Saverio was very attentive and gracious. Check in and out couldn’t have been easier! "
United States
John L.
The price is ￥15,675
￥23,139 total
includes taxes & fees
Oct 25 - Oct 26
La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!
A courtyard with a stone pathway, potted plants, and a building with multiple windows and a door.

4. Elegant Countryside Retreat

Elegant Countryside Retreat
Città di Castello
9.4 out of 10, Exceptional, (29 reviews)
"Enjoyed evenings near that fireplace, really nice ambiance when winding down after excursions into town. Garden’s a good spot to chill if you want some fresh air as well."
United States
Anonymous traveler
The price is ￥16,997
￥45,223 total
includes taxes & fees
Oct 22 - Oct 23
Elegant Countryside Retreat
A building with a balcony, multiple windows, and a door.

5. Dolce Rosa Centro Storico

Dolce Rosa Centro Storico
Sansepolcro
9.6 out of 10, Exceptional, (13 reviews)
"Ottimo rapporto qualità prezzo camera carina... un unico neo mancavano i tappi di vasca e bidet..."
Italy
Sergio
The price is ￥8,749
￥9,624 total
includes taxes & fees
Nov 16 - Nov 17
Dolce Rosa Centro Storico
A modern kitchen with a central island, built-in appliances, and a dining area with a table and chairs.

6. The Cyclist. Pedal your way to your ideal stay!

The Cyclist. Pedal your way to your ideal stay!
Parlesca
The price is ￥14,076
￥17,275 total
includes taxes & fees
Nov 1 - Nov 2
The Cyclist. Pedal your way to your ideal stay!
A stone building with a sloped roof, a covered porch, and a small garden area with potted plants.

7. Apartment 'Lavanda ad Antico Casale '700' with Shared Pool & Wi-Fi

Apartment 'Lavanda ad Antico Casale '700' with Shared Pool & Wi-Fi
Umbertide
8.0 out of 10, Very good, (1 review)
"Pros: Location in the mountains is superb, very friendly& supportive staff, fair price Cons: Only very small windows in the appartment, thus dark and nearly no chance for fresh cold air in the night. Due to the size of the location the pool was overcrowded and too less sun chairs. Photos better than reality."
United States
Anonymous traveler
The price is ￥41,614
￥54,620 total
includes taxes & fees
Oct 22 - Oct 23
Apartment 'Lavanda ad Antico Casale '700' with Shared Pool & Wi-Fi
A stone building with a sloped roof, a covered porch, and a small garden area.

8. Apartment 'Glicine ad Antico Casale '700' with Shared Pool & Wi-Fi

Apartment 'Glicine ad Antico Casale '700' with Shared Pool & Wi-Fi
Umbertide
The price is ￥52,017
￥65,023 total
includes taxes & fees
Oct 30 - Oct 31
Apartment 'Glicine ad Antico Casale '700' with Shared Pool & Wi-Fi
An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

9. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is ￥22,509
￥25,115 total
includes taxes & fees
Nov 2 - Nov 3
B&B Piccolo Hotel
A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

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

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful location. Can't wait to go back."
United States
Dawn H.
The price is ￥16,617
￥17,328 total
includes taxes & fees
Oct 22 - Oct 23
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Exterior detail

11. 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 ￥19,194
￥22,393 total
includes taxes & fees
Oct 22 - Oct 23
Home of the Sun
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

12. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is ￥16,311
￥18,653 total
includes taxes & fees
Oct 23 - Oct 24
Vicolo Della Scala Rooms - Il Sole
A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

13. Happy Nest Tuscany Between Florence and Rome

Happy Nest Tuscany Between Florence and Rome
Castiglion Fiorentino
The price is ￥7,997
￥11,907 total
includes taxes & fees
Oct 22 - Oct 23
Happy Nest Tuscany Between Florence and Rome
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

14. 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 ￥20,512
￥23,274 total
includes taxes & fees
Oct 25 - Oct 26
San Michele al Borgo
Exterior

15. Wohnung la Mimosa by Interhome

Wohnung la Mimosa by Interhome
Cortona
The price is ￥36,255
￥37,144 total
includes taxes & fees
Oct 22 - Oct 23
Wohnung la Mimosa by Interhome
A table with food and drinks, a stone pillar, and a scenic view of hills and trees.

16. 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 traveler
The price is ￥56,649
￥57,004 total
includes taxes & fees
Oct 29 - Oct 30
Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
A modern apartment with a kitchen, dining area, living room, and a balcony.

17. Apartment 'Blu Trasimeno' with Private Garden, Wi-Fi and Air Conditioning

Apartment 'Blu Trasimeno' with Private Garden, Wi-Fi and Air Conditioning
Tuoro sul Trasimeno
10.0 out of 10, Exceptional, (1 review)
"Pros: Hervorragende Ausstattung der Küche. Sehr gute Kommunikation mit dem Gastgeber. Sehr sauber und liebevoll eingerichtet."
Germany
Anonymous traveler
The price is ￥26,303
￥34,300 total
includes taxes & fees
Oct 25 - Oct 26
Apartment 'Blu Trasimeno' with Private Garden, Wi-Fi and Air Conditioning
A bedroom with a checkered floor, a bed, a television, a dresser, and a wardrobe.

18. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is ￥33,444
￥37,055 total
includes taxes & fees
Nov 5 - Nov 6
CASA AMBRA
A black dog sitting on stone steps in front of a brown double door with a metal decorative archway.

19. Beppina Vacation Home, a traditional Cortona-style house, in the center, pets welcome

Beppina Vacation Home, a traditional Cortona-style house, in the center, pets welcome
Cortona Old Town
The price is ￥16,455
￥20,287 total
includes taxes & fees
Oct 28 - Oct 29
Beppina Vacation Home, a traditional Cortona-style house, in the center, pets welcome
Holiday Home Exterior [summer]

20. Holiday Home in Umbria near Renaissance Castle

Holiday Home in Umbria near Renaissance Castle
Città di Castello
9.6 out of 10, Exceptional, (12 reviews)
"Good value overall considering included pool use and garden space. The location offered beautiful views that enhanced our relaxation throughout the stay."
United States
Anonymous traveler
The price is ￥30,040
￥40,494 total
includes taxes & fees
Oct 22 - Oct 23
Holiday Home in Umbria near Renaissance Castle
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 Calzolaro Hotel Reviews

Hotel Sant'Ercolano

Hotel Sant'Ercolano

8/10 Good
"Very clean throughout. All staff very helpful. Would be good if there was kettle and drinks facilities in the rooms."
Laura 2-night trip
Posted 12 hours ago
Hotel Sant'Ercolano

Find out more about Calzolaro

Search for holiday rentals in Calzolaro on Expedia! You can easily find your home rentals, villas, holiday apartments in Calzolaro using one of the methods below:

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Look no further and take a look at our great range of rental properties in Calzolaro!

Frequently asked questions

Can I find vacation rentals in Calzolaro?

Yes, we have vacation rentals close to top local attractions in Calzolaro, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Calzolaro?

Holiday Home in Umbria with Pool: This vacation home rental near Calzolaro offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Calzolaro?

While exploring the area, visit family-friendly sights like Aboca Museum, or get outside and enjoy nature at Isola Maggiore. In the larger area, you’ll find Historic Town Montone and Civitella Ranieri Castle.

What’s a vacation rental in Calzolaro like?

Vacation rentals are private properties you can stay in for a long or short time in Calzolaro. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.