Oliveto Vacation Rentals

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Our top choices for Oliveto vacation rentals

Apartment in Civitella in val di Chiana

Appatamento Castello 2px - B&B Borgo di Oliveto
The price is ¥14,548
¥17,821 total
includes taxes & fees
Jan 17 - Jan 18, 2026
Appatamento Castello 2px - B&B Borgo di Oliveto

Apartment in Civitella in val di Chiana

Alley: nice 2px studio - Borgo di Oliveto
The price is ¥14,548
¥17,821 total
includes taxes & fees
Jan 17 - Jan 18, 2026
Alley: nice 2px studio - Borgo di Oliveto

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 ¥20,643
¥22,707 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Villa Cassia di Baccano

Townhouse in Gaiole in Chianti

L' Eroico
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

Townhouse in Monte San Savino

DormiVeglia B&B
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

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ¥10,970
¥12,613 total
includes taxes & fees
Dec 18 - Dec 19
Abbadia Sicille Relais

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 ¥18,449
¥21,021 total
includes taxes & fees
Jan 7 - Jan 8, 2026
San Michele al Borgo

Vacation Home in Montecchio

Montecchio di Cortona
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 ¥10,911
¥14,184 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Montecchio di Cortona

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 ¥19,342
¥22,367 total
includes taxes & fees
Dec 19 - Dec 20
THE MONNA LISA RESORT
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 ¥25,624
¥28,186 total
includes taxes & fees
Dec 21 - Dec 22
Relais Villa Belpoggio - Residenza d'Epoca

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 ¥18,185
¥34,005 total
includes taxes & fees
Jan 16 - Jan 17, 2026
La casa di Laura

Aparthotel in Rapolano Terme

Podere La Chiusella
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

Apartment in Montevarchi

Cennano Suite - enter apartment
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 ¥10,002
¥20,549 total
includes taxes & fees
Dec 27 - Dec 28
Cennano Suite - enter apartment

Townhouse in Gaiole in Chianti

Rocca di Castagnoli
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 ¥37,197
¥42,371 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Rocca di Castagnoli

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 ¥14,171
¥16,682 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Cameracaffè Centro
10.0 out of 10, Exceptional, (3)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is ¥17,185
¥21,004 total
includes taxes & fees
Dec 18 - Dec 19
Cortona Shabby Chic House<br>(Independent & balcony)

Villa in Foiano della Chiana

Artisti del Cavallo Tourism
8.4 out of 10, Very Good, (24)
"Good house for one night. "
Germany
Heiner
The price is ¥12,928
¥14,585 total
includes taxes & fees
Dec 19 - Dec 20
Artisti del Cavallo Tourism

Residence in Monte San Savino

Castello di Gargonza
3.0 star property
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

Vacation 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 ¥16,366
¥19,639 total
includes taxes & fees
Dec 22 - Dec 23
House in the Cortona countryside

Apartment in Arezzo Centro Storico

Living suite Verdeconiglio in the heart of Arezzo
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 ¥14,730
¥16,203 total
includes taxes & fees
Jan 12 - Jan 13, 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 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 vacation rentals in Oliveto?

Yes, we have vacation rentals near the most popular attractions in Oliveto, or you can go with a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Oliveto?

Borgo Argiano: You might want to consider this vacation home rental near Oliveto, which is located on a river and has a balcony, a terrace, and a barbecue grill 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 vacation with a garden and a library.

How many vacation rentals are there in Oliveto?

With 6 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Oliveto like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Oliveto. Vacation rentals feature extras such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion 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 an attractive option for family trips or small group gatherings.