Oliveto Holiday Rentals

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Holiday Rentals in Oliveto

Appatamento Castello 2px - B&B Borgo di Oliveto

Civitella in val di Chiana
The price is AU$175
includes taxes & fees
4 Jan - 5 Jan 2026
Appatamento Castello 2px - B&B Borgo di Oliveto

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 AU$233
includes taxes & fees
9 Dec - 10 Dec
Villa Cassia di Baccano

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

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 AU$216
includes taxes & fees
19 Dec - 20 Dec
THE MONNA LISA RESORT

Abbadia Sicille Relais

4.0 star property
Trequanda
8.8 out of 10, Excellent, (165)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is AU$127
includes taxes & fees
15 Dec - 16 Dec
Abbadia Sicille Relais

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

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

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 AU$147
includes taxes & fees
15 Dec - 16 Dec
Cameracaffè Centro

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 AU$136
includes taxes & fees
8 Jan - 9 Jan 2026
Artisti del Cavallo Tourism

San Michele al Borgo

Castiglion Fiorentino
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is AU$220
includes taxes & fees
9 Dec - 10 Dec
San Michele al Borgo

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

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 AU$223
includes taxes & fees
3 Jan - 4 Jan 2026
Casa Vacanze Le Fornaci

Holiday home with panoramic terrace ideal for families and couples

Cortona
The price is AU$164
includes taxes & fees
9 Dec - 10 Dec
Holiday home with panoramic terrace ideal for families and couples

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Monteaperti
10.0 out of 10, Exceptional, (2)
"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"
United States
Ian F.
The price is AU$302
includes taxes & fees
9 Dec - 10 Dec
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Montecchio di Cortona

Montecchio
9.0 out of 10, Wonderful, (2)
"Tutto estremamente pulito ed ordinato.... Spero di aver modo di poterci tornare presto..."
Italy
Monica S.
The price is AU$140
includes taxes & fees
31 Dec - 1 Jan 2026
Montecchio di Cortona

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 AU$272
includes taxes & fees
9 Dec - 10 Dec
Relais Villa Belpoggio - Residenza d'Epoca

Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi

Cortona
9.0 out of 10, Wonderful, (2)
"Pros: Il camino è stato come tornare bambini.Atmosfera Natalizia e tanto di più. Cons: Il Bidè non funzionava."
Italy
Anonymous traveller
The price is AU$195
includes taxes & fees
5 Jan - 6 Jan 2026
Apartment "La Vecchia Fornace La Casina" with Shared Pool & Wi-Fi

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 AU$249
includes taxes & fees
9 Dec - 10 Dec
The window on the tower apartment new castiglion fiorentino

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 AU$122
includes taxes & fees
31 Dec - 1 Jan 2026
Casa Da Vinci for two

Teo's house is the ideal home for relaxation, centrally located in Anghiari

Anghiari
10.0 out of 10, Exceptional, (1)
"The apartment was clean and cozy. I thoroughly enjoyed my stay. It is located on Corso Giacomo Matteotti and directly across from the main town square. Although not in the walled, traditional historic center, its in a very convenient and central location for exploring the entire town. The host Francesca was extremely helpful and checked in often."
United States
Danna J.
The price is AU$412
includes taxes & fees
9 Dec - 10 Dec
Teo's house is the ideal home for relaxation, centrally located in Anghiari
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

Everything you need to know about Oliveto holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oliveto holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oliveto holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Oliveto holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oliveto. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oliveto holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oliveto holiday rentals we have selected for you start as low as AU$127 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oliveto rentals

At Expedia, we put the best Oliveto holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oliveto rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oliveto holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oliveto. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 of 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 a coffee maker. 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.