Scheggia Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Scheggia vacation rentals

Pool
Cottage La Fagianaia

Cottage La Fagianaia

Cottage La Fagianaia
Anghiari
The price is ￥23,917
￥27,229 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Cottage La Fagianaia
Lobby lounge
Villa Cassia di Baccano

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ￥18,122
￥19,934 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Villa Cassia di Baccano
Balcony
Cameracaffè Centro

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
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 ￥12,652
￥15,022 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Cameracaffè Centro
Classic Double or Twin Room, 1 Double Bed | Premium bedding, down comforters, pillowtop beds, minibar
THE MONNA LISA RESORT

THE MONNA LISA RESORT

THE MONNA LISA RESORT
Arezzo
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 ￥21,895
￥25,187 total
includes taxes & fees
Jan 2 - Jan 3, 2026
THE MONNA LISA RESORT
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
Villa La Ginestra

Villa La Ginestra

Villa La Ginestra
Subbiano
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
Balcony
Dolce Rosa Centro Storico

Dolce Rosa Centro Storico

Dolce Rosa Centro Storico
Sansepolcro
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
Free daily cooked-to-order breakfast
San Michele al Borgo

San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is ￥19,176
￥21,828 total
includes taxes & fees
Jan 8 - Jan 9, 2026
San Michele al Borgo
Exterior
Locanda Guidi

Locanda Guidi

Locanda Guidi
Sansepolcro
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
Pool
Elegant Countryside Retreat

Elegant Countryside Retreat

Elegant Countryside Retreat
Città di Castello
The price is ￥3,359
￥30,910 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Elegant Countryside Retreat
Lunch, dinner served; Italian cuisine, garden views
Locanda del Viandante

Locanda del Viandante

Locanda del Viandante
Anghiari
9.0 out of 10, Wonderful, (6)
"Smuk beliggenhed - meget autentisk på den gode måde"
Denmark
tina
The price is ￥22,542
￥24,796 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Locanda del Viandante
Terrace/patio
Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci
Pergine Valdarno
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 ￥20,706
￥23,327 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Casa Vacanze Le Fornaci
Luxury Room, Jetted Tub, City View | Free WiFi, bed sheets
B&B 52cento

B&B 52cento

B&B 52cento
Arezzo Centro Storico
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 ￥12,623
￥14,987 total
includes taxes & fees
Jan 8 - Jan 9, 2026
B&B 52cento
Fridge, oven, stovetop, electric kettle
The window on the tower apartment new castiglion fiorentino

The window on the tower apartment new castiglion fiorentino

The window on the tower apartment new castiglion fiorentino
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 ￥18,367
￥25,714 total
includes taxes & fees
Dec 27 - Dec 28
The window on the tower apartment new castiglion fiorentino
Property grounds
Deluxe room Cartazucchero in the heart of Arezzo

Deluxe room Cartazucchero in the heart of Arezzo

Deluxe room Cartazucchero in the heart of Arezzo
Arezzo Centro Storico
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 ￥11,902
￥13,092 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Deluxe room Cartazucchero in the heart of Arezzo
Dining
LE ORTENSIE Independent mini-apartment outdoor space and small garden

LE ORTENSIE Independent mini-apartment outdoor space and small garden

LE ORTENSIE Independent mini-apartment outdoor space and small garden
Arezzo
10.0 out of 10, Exceptional, (1)
"From the moment we checked in, Giacinta was a gem to talk to, even with her broken English :). The apartment was very clean and the A/C worked great, specially after a busy day outside. Just a short drive to the historic district and also to some wineries and vineyards. Overall I will rate this place a 10 and recommend to anyone visiting Arezzo in the Tuscany region of Italy."
United States
Jose P.
The price is ￥17,816
￥27,734 total
includes taxes & fees
Jan 2 - Jan 3, 2026
LE ORTENSIE Independent mini-apartment outdoor space and small garden
1 bedroom, iron/ironing board, free WiFi, bed sheets
Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4

Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Arezzo Centro Storico
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 ￥15,153
￥28,010 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Business center
Allegra Toscana - Affittacamere Guest house

Allegra Toscana - Affittacamere Guest house

Allegra Toscana - Affittacamere Guest house
Arezzo Centro Storico
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
Comfort Apartment, 3 Bedrooms | View from property
Rustic Holiday Home in Citta di Castello With Swimming Pool

Rustic Holiday Home in Citta di Castello With Swimming Pool

Rustic Holiday Home in Citta di Castello With Swimming Pool
Città di Castello
The price is ￥24,333
￥26,766 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Rustic Holiday Home in Citta di Castello With Swimming Pool
Property grounds
Living suite Verdeconiglio in the heart of Arezzo

Living suite Verdeconiglio in the heart of Arezzo

Living suite Verdeconiglio in the heart of Arezzo
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1)
"It was a beautiful and quiet part of town and was very close to everything. The property manager spoke pretty good English which made everything much easier. It is a beautiful comforting and clean stay in the heart of Arezzo. Thank you. Era una zona bellissima e tranquilla della città, vicinissima a tutto. Il gestore parlava un ottimo inglese, il che ha reso tutto molto più semplice. È stato un soggiorno splendido, confortevole e pulito nel cuore di Arezzo. Grazie."
United States
Andrew T.
The price is ￥14,878
￥16,366 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Living suite Verdeconiglio in the heart of Arezzo
Pool
La Fonte, our quaint little west facing cottage for two people.

La Fonte, our quaint little west facing cottage for two people.

La Fonte, our quaint little west facing cottage for two people.
Cortona
The price is ￥25,347
￥33,612 total
includes taxes & fees
Dec 29 - Dec 30
La Fonte, our quaint little west facing cottage for two people.
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 Scheggia 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 Scheggia

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

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

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

Frequently asked questions

Can I find vacation rentals in Scheggia?

Yes, there are vacation rentals near top sights in Scheggia, or you can choose a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental in Scheggia?

Beautiful tuscan villa with pool, ideal for groups: You might like this vacation home rental near Scheggia. It is located in the mountains and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 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 Scheggia?

Explore the area and family-friendly sights such as Aboca Museum, or get out into nature at a spot like Piazza Guido Monaco. Anghiari Historic Town Center and Fortezza Medicea are a couple of places you'll find in the larger area.

What’s a vacation rental in Scheggia like?

Vacation rentals are private properties where you can stay for a long or short time in Scheggia. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family gatherings.