Chiaveretto Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Chiaveretto vacation rentals

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 ￥18,492
￥20,341 total
includes taxes & fees
Jan 17 - Jan 18, 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 ￥13,194
￥15,615 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Cameracaffè Centro
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
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
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
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 ￥21,973
￥25,276 total
includes taxes & fees
Jan 2 - Jan 3, 2026
THE MONNA LISA RESORT
Daily buffet breakfast (EUR 10 per person)
DormiVeglia B&B

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (27)
"This was our favourite B&B. The owner Simona was absolutely wonderful. The hot tub in our room was out of this world. If you have the chance to visite this gem…DO IT!!"
Canada
Claude
DormiVeglia B&B
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 ￥18,911
￥21,539 total
includes taxes & fees
Jan 8 - Jan 9, 2026
San Michele al Borgo
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 ￥22,533
￥24,786 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Locanda del Viandante
Pool
Elegant Countryside Retreat

Elegant Countryside Retreat

Elegant Countryside Retreat
Città di Castello
The price is ￥2,244
￥29,784 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Elegant Countryside Retreat
Fridge, microwave, oven, stovetop
Cennano Suite - enter apartment

Cennano Suite - enter apartment

Cennano Suite - enter apartment
Montevarchi
10.0 out of 10, Exceptional, (3)
"After and before the tourist rushes of Florence. I enjoyed a few very quiet and relaxing days in a beautiful and spacious place. "
Germany
Judith T.
The price is ￥10,098
￥20,747 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Cennano Suite - enter apartment
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 ￥11,897
￥13,087 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Deluxe room Cartazucchero in the heart of Arezzo
Terrace/patio
Casa Da Vinci for two

Casa Da Vinci for two

Casa Da Vinci for two
Castiglion fibocchi
8.0 out of 10, Very Good, (1)
"Sauber gemütlich, nette Atmosphäre Einrichtung ist ausreichend."
Germany
Perdita I.
The price is ￥7,344
￥12,485 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Casa Da Vinci for two
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)
"Stayed in the top floor room with the terrace and seating area. Definitely a great decision. Arrezo was the starting point of our Tuscany tour and glad we spent an extra night and day. Great room super convenient to town and the train station. "
United States
Edward
The price is ￥12,618
￥14,982 total
includes taxes & fees
Jan 13 - Jan 14, 2026
B&B 52cento
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
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 ￥17,878
￥27,831 total
includes taxes & fees
Jan 2 - Jan 3, 2026
LE ORTENSIE Independent mini-apartment outdoor space and small garden
Coffee/tea maker, cookware/dishes/utensils
Alley: nice 2px studio - Borgo di Oliveto

Alley: nice 2px studio - Borgo di Oliveto

Alley: nice 2px studio - Borgo di Oliveto
Civitella in val di Chiana
The price is ￥14,688
￥17,993 total
includes taxes & fees
Jan 30 - Jan 31, 2026
Alley: nice 2px studio - Borgo di Oliveto
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 ￥15,147
￥27,999 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Tolletta 10 e Lode - One Bedroom House, Sleeps 4
Front of property
Locanda Antico Borgo

Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (20)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
The price is ￥16,663
￥18,330 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Locanda Antico Borgo
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 ￥14,872
￥16,359 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Living suite Verdeconiglio in the heart of Arezzo
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 Chiaveretto 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 11 days ago
Monastero di Cortona Hotel & Spa

Find out more about Chiaveretto

Search for holiday rentals in Chiaveretto on Expedia! You can easily find your home rentals, villas, holiday apartments in Chiaveretto 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 Chiaveretto!

Frequently asked questions

Can I find vacation rentals in Chiaveretto?

Yes, we give you a choice of vacation rentals near the most popular local attractions in Chiaveretto, or you can select a more remote option if you want a relaxing place to stay.

What are some of the best vacation rentals in Chiaveretto?

Beautiful tuscan villa with pool, ideal for groups: You might like this vacation home rental near Chiaveretto. 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 Chiaveretto?

While exploring the area, visit family-friendly sights like Aboca Museum, or get outside and enjoy nature at Piazza Guido Monaco. In the larger area, you’ll find Casa Vasari House Museum and Cathedral of Saints Peter and Donato.

What’s a vacation rental in Chiaveretto like?

Vacation rentals are private properties you can book for several days or longer in Chiaveretto. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a small group gathering.