Toppole Holiday Rentals

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Check prices for these dates

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Toppole holiday rentals

Lobby lounge
Villa Cassia di Baccano

Townhouse in Loro Ciuffenna

Villa Cassia di Baccano
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is HK$913
HK$1,005 total
includes taxes & fees
8 Jan - 9 Jan 2026
Villa Cassia di Baccano
Balcony
Cameracaffè Centro

Townhouse in Arezzo Centro Storico

Cameracaffè Centro
8.6 out of 10, Excellent, (179)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is HK$659
HK$780 total
includes taxes & fees
18 Jan - 19 Jan 2026
Cameracaffè Centro
Balcony
Dolce Rosa Centro Storico

Townhouse in Sansepolcro

Dolce Rosa Centro Storico
9.6 out of 10, Exceptional, (13)
"Ottimo rapporto qualità prezzo camera carina... un unico neo mancavano i tappi di vasca e bidet..."
Italy
Sergio
Dolce Rosa Centro Storico
Exterior
Locanda Guidi

Townhouse in Sansepolcro

Locanda Guidi
9.0 out of 10, Wonderful, (2)
"No one in reception on arrival or departure. Only one small bottle of water in the room. ID cards left in the entry hall with no supervision. Very nice room, excellent location, very clean but totally lacking in "accoglienza"."
Ireland
Michael
Locanda Guidi
Free daily cooked-to-order breakfast
San Michele al Borgo

Townhouse in Castiglion Fiorentino

San Michele al Borgo
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is HK$956
HK$1,089 total
includes taxes & fees
8 Jan - 9 Jan 2026
San Michele al Borgo
Pool
Elegant Countryside Retreat

Apartment in Città di Castello

Elegant Countryside Retreat
The price is HK$168
HK$1,541 total
includes taxes & fees
10 Jan - 11 Jan 2026
Elegant Countryside Retreat
Premium bedding, down duvets, pillow-top beds, minibar
THE MONNA LISA RESORT

Townhouse in Arezzo

THE MONNA LISA RESORT
9.6 out of 10, Exceptional, (8)
"Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. "
United States
Bart
The price is HK$1,152
HK$1,323 total
includes taxes & fees
1 Jan - 2 Jan 2026
THE MONNA LISA RESORT
Free WiFi, bed sheets
B&B 52cento

Townhouse in Arezzo Centro Storico

B&B 52cento
8.0 out of 10, Very good, (73)
"Exactly how it is described and very near the train station. Walkable distance to all the things to do around there. I really enjoyed my stay there. "
United States
Maria de Lourdes
The price is HK$629
HK$747 total
includes taxes & fees
8 Jan - 9 Jan 2026
B&B 52cento
Business centre
Allegra Toscana - Affittacamere Guest house

Townhouse in Arezzo Centro Storico

Allegra Toscana - Affittacamere Guest house
7.0 out of 10, Good, (16)
"Great location in Arezzo, easy and simple to find and access. Everything was exactly as we needed although we did not need to stay long."
United Kingdom
Justin
Allegra Toscana - Affittacamere Guest house
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
Villa La Ginestra

Townhouse in Subbiano

Villa La Ginestra
9.6 out of 10, Exceptional, (5)
"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."
Canada
Philippe
Villa La Ginestra
Property grounds
La casa di Laura

Apartment in Cortona Old Town

La casa di Laura
10.0 out of 10, Exceptional, (1)
"Best sleep I’ve had in a long time. Very quiet area. Beautiful views. Absolutely gorgeous. Water and coffee were provided. Clean. Bruno was very patient with us with the language barrier. We also had trouble getting to the place because we were not getting service on our phone till we connected to WiFi. Bruno met us and showed us where to park after showing us the way to the apartment. Very steep climb up to the apartment from the parking area, but Cortona is overall steep. You will climb up...
United States
Angie F.
The price is HK$824
HK$1,584 total
includes taxes & fees
8 Jan - 9 Jan 2026
La casa di Laura
Lunch, dinner served; Italian cuisine, garden views
Locanda del Viandante

Townhouse in Anghiari

Locanda del Viandante
9.0 out of 10, Wonderful, (6)
"Smuk beliggenhed - meget autentisk på den gode måde"
Denmark
tina
The price is HK$1,124
HK$1,236 total
includes taxes & fees
8 Jan - 9 Jan 2026
Locanda del Viandante
1 bedroom, travel cot, free WiFi
City / Village Apartment in Cortona with 1 bedrooms sleeps 2

Apartment in Cortona Old Town

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
10.0 out of 10, Exceptional, (6)
"This place was such a great find! So central and easily reachable. We really enjoyed our stay!"
United States
Julie R.
The price is HK$856
HK$893 total
includes taxes & fees
8 Jan - 9 Jan 2026
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
1 bedroom, desk, iron/ironing board, WiFi
Cortona Shabby Chic House<br>(Independent & balcony)

Apartment in Cortona Old Town

Cortona Shabby Chic House<br>(Independent & balcony)
10.0 out of 10, Exceptional, (3)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is HK$866
HK$1,058 total
includes taxes & fees
2 Jan - 3 Jan 2026
Cortona Shabby Chic House<br>(Independent & balcony)
Fridge, oven, stovetop, electric kettle
The window on the tower apartment new castiglion fiorentino

Apartment in Castiglion fiorentino

The window on the tower apartment new castiglion fiorentino
10.0 out of 10, Exceptional, (1)
"Large apartment 4 floors above the town. Easy walking to anywhere in the area. Great shower and large bathroom. Equipped kitchen with big refrigerator. Living room with TV and dining table and couch. Large bedroom with fan. Also, there is a hairdryer and ironing board and iron. You are very close to walk to restaurants and stores, About a mile from the train station up a hill but the hostess helped us with transport.Overall, an excellent stay for my wife and I. (Be aware the room is 4...
United States
aric w.
The price is HK$916
HK$1,282 total
includes taxes & fees
27 Dec - 28 Dec
The window on the tower apartment new castiglion fiorentino
Property grounds
Deluxe room Cartazucchero in the heart of Arezzo

Apartment in Arezzo Centro Storico

Deluxe room Cartazucchero in the heart of Arezzo
10.0 out of 10, Exceptional, (2)
"From all the places we stayed during our 13-day trip to Italy, this was by far our favorite. Fabio was incredibly communicative and friendly right from the start, sending us clear instructions on how to get there. He greeted us at the door with such warmth that it truly felt like we were staying with family. The room was spotless, beautifully decorated, and generously stocked with water, cookies, pastries, and other treats. It had the comfort and attention to detail of a hotel, yet the warmth of...
United States
Hector
The price is HK$593
HK$653 total
includes taxes & fees
19 Jan - 20 Jan 2026
Deluxe room Cartazucchero in the heart of Arezzo
Exterior
Sanniccolo'20 - Historic Residence

Apartment in Arezzo Centro Storico

Sanniccolo'20 - Historic Residence
10.0 out of 10, Exceptional, (1)
"We stayed in the apartment for two nights with a family of four. The apartment is in a great location that is walkable to all the main areas of Arezzo. Close to shops and restaurants and the main piazza. The apartment was clean and plenty of room for a family of four. The communication was great and very easy to locate the apartment from the train station and enter the building. We loved our stay and would definitely stay again."
United States
Tony V.
The price is HK$1,072
HK$1,291 total
includes taxes & fees
28 Dec - 29 Dec
Sanniccolo'20 - Historic Residence
1 bedroom, iron/ironing board, free WiFi, bed sheets
Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Holiday Home in Arezzo Centro Storico

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
10.0 out of 10, Exceptional, (1)
" La casa pulitissima è molto bella, l’host molto disponibile e gentile, risponde sempre e anche subito. La posizione ottimale per fare il giro dei mercatini e di tutta la città. Consigliatissima "
Italy
Maria Gemma
The price is HK$756
HK$1,397 total
includes taxes & fees
19 Jan - 20 Jan 2026
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Terrace/patio
Casa Vacanze Le Fornaci

Apartment in Pergine Valdarno

Casa Vacanze Le Fornaci
9.4 out of 10, Exceptional, (3)
"We absolutely loved our stay at this hotel. The suite was perfect and the restaurant had probably the best food I have had in Tuscany. We definitely plan to stay there again."
United States
Gregory
The price is HK$1,032
HK$1,163 total
includes taxes & fees
3 Jan - 4 Jan 2026
Casa Vacanze Le Fornaci
1 bedroom, iron/ironing board, free WiFi, bed sheets
House in the Cortona countryside

Holiday Home in Fratticciola

House in the Cortona countryside
10.0 out of 10, Exceptional, (1)
"Host was extremely welcoming. Met us when we arrived and explained usage of all the amenities, including the clothes washer. Cottage was quintessential Rural Italian home. The hostess even provided us with some local wine and homemade biscotti. "
United States
Nancy F.
The price is HK$824
HK$989 total
includes taxes & fees
26 Dec - 27 Dec
House in the Cortona countryside
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 Toppole Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Everything was perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!"
Sabrina 4-night trip
Posted 7 days ago
Monastero di Cortona Hotel & Spa

Find out more about Toppole

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

  • View our selection of featured holiday rentals in Toppole
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  • Enter your travel dates to view the best deals on holiday rentals in Toppole while they last

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

Frequently asked questions

Are there holiday rentals in Toppole?

Yes, there are holiday rentals close to the most popular sights in Toppole, or you can select a more secluded option if you're looking for a relaxing stay. Toppole is known for its wineries.

What are some of the best holiday rentals that Toppole has to offer?

Farmhouse in the hills with panoramic view and swimming pool: This holiday home rental outside of Toppole is located in a rural location, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

What’s there to see and do in Toppole?

Explore the area and family-friendly sights such as Aboca Museum, or get out into nature at a spot like Piazza Guido Monaco. In the wider area, you’ll find Anghiari Historic Town Center and Madonna del Parto Museum.

What’s a holiday rental in Toppole like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Toppole. Holiday rentals feature amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.