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Our top choices for Oliveto holiday rentals

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (166)
The price is ฿2,303
฿2,644 total
includes taxes & fees
17 Dec - 18 Dec
Abbadia Sicille Relais

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 ฿4,557
฿5,012 total
includes taxes & fees
7 Jan - 8 Jan 2026
Villa Cassia di Baccano

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 ฿3,095
฿3,626 total
includes taxes & fees
7 Jan - 8 Jan 2026
Cameracaffè Centro

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 ฿4,205
฿4,773 total
includes taxes & fees
11 Jan - 12 Jan 2026
San Michele al Borgo

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

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (12)
"Monica was the friendliest most enthusiastic host we’ve stayed with. Everything from her greeting to the amazing breakfast was perfect. She does a lot of baking, so the breakfast was really a treat and you could also get eggs cooked in various ways. The room was a little small but very comfortable. Parking was on the street, but it was fairly close and easy."
United States
Perry
L' Eroico

Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.4 out of 10, Exceptional, (30)
"Et sjarmerende lite B&B. Har nok vært utrolig vakkert i sine glansdager, men områdene rundt bærer preg av lite vedlikehold. Leiligheten var helt grei for en overnatting. Gulvet på badet var ikke rent. Når vi tørket opp etter oss ble håndkleet møkkete. Men overnattingen var helt grei alt i alt. Når vi skulle sjekke ut var det ikke et menneske å se, resepsjonen var stengt. Endte med å sette nøklene i døra og dra da alt var betalt ved bestilling."
Norway
Elisabeth
Podere La Chiusella

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 ฿2,543
฿3,019 total
includes taxes & fees
11 Jan - 12 Jan 2026
B&B 52cento

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 ฿3,939
฿4,556 total
includes taxes & fees
19 Dec - 20 Dec
THE MONNA LISA RESORT

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24)
"Good house for one night. "
Germany
Heiner
The price is ฿2,684
฿3,027 total
includes taxes & fees
17 Dec - 18 Dec
Artisti del Cavallo Tourism

Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (35)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is ฿5,214
฿5,735 total
includes taxes & fees
19 Dec - 20 Dec
Relais Villa Belpoggio - Residenza d'Epoca

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

La Murata

La Murata
Rapolano Terme
9.0 out of 10, Wonderful, (11)
"Amazingly beautiful place! Wish i could have stayed longer to enjoy the view but was just passing through. The apartment was so cute and clean. Any family would enjoy staying here. I would stay here again if i were in the area."
United States
Elizabeth
The price is ฿4,723
฿5,343 total
includes taxes & fees
19 Dec - 20 Dec
La Murata

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 ฿4,171
฿4,699 total
includes taxes & fees
3 Jan - 4 Jan 2026
Casa Vacanze Le Fornaci

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

Rocca di Castagnoli

Rocca di Castagnoli
Gaiole in Chianti
9.2 out of 10, Wonderful, (28)
"It was wonderful to stay in a castle in Tuscany no less Every person we met was attentive and kind We were staying near friends and didn’t hang around the grounds much or use the pool but everything seemed well kept It’s really a place to retreat to eat at and sleep at which served our purpose well "
Canada
Shingo
The price is ฿7,568
฿8,621 total
includes taxes & fees
13 Jan - 14 Jan 2026
Rocca di Castagnoli

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (39)
"All of the hotel staff did an outstanding job. Our room had everything we needed and the restaurant was great. Breakfast was exceptional. Special shoutout to Neri, the owner, for taking such good care of us. "
United States
Diane
Castello di Gargonza

Room in Apartment - Two-room Apartment

Room in Apartment - Two-room Apartment
Arezzo
10.0 out of 10, Exceptional, (1)
"A little tricky to locate but friendly staff and very walkable to see the sites."
Canada
Thelma
The price is ฿3,885
฿4,496 total
includes taxes & fees
15 Jan - 16 Jan 2026
Room in Apartment - Two-room Apartment

Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
The price is ฿8,140
฿9,139 total
includes taxes & fees
18 Dec - 19 Dec
Albergo Diffuso Borgo Santo

Two-room Apartment for 3 People With Kitchen and Private Bathroom

Two-room Apartment for 3 People With Kitchen and Private Bathroom
Arezzo
8.0 out of 10, Very good, (1)
"The property is in a great location in Arezzo and the owner communicated clearly, thoroughly with us and this was much appreciated since we are still novice VRBO users. Not having a designated parking spot caused some frustration when we ended up finding an open spot a block away. "
United States
Robert
The price is ฿4,440
฿5,106 total
includes taxes & fees
4 Jan - 5 Jan 2026
Two-room Apartment for 3 People With Kitchen and Private Bathroom
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 Oliveto Hotel Reviews

Find out more about Oliveto

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

Frequently asked questions

Can I find holiday rentals in Oliveto?

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

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

Borgo Argiano: This holiday home rental outside Oliveto is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Oliveto?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Oliveto stay.

What’s there to see and do in Oliveto?

While exploring the area, visit family-friendly sights like Siena Circuit, or get outside and enjoy nature at Piazza Guido Monaco. Arezzo Equestrian Centre and Villa a Sesta Polo Club are a couple of places you'll find in the wider area.

What’s a holiday rental in Oliveto like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oliveto. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for families.