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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sep - 6 Sep

Our top choices for Oliveto holiday rentals

Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (173 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ฿5,465
฿6,126 total
includes taxes & fees
13 May - 14 May
Abbadia Sicille Relais
Lobby

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ฿4,937
฿5,431 total
includes taxes & fees
25 May - 26 May
Villa Cassia di Baccano
Lunch and dinner served, local cuisine

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (40 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
The price is ฿8,213
฿9,186 total
includes taxes & fees
13 May - 14 May
Castello di Gargonza
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (32 reviews)
"Beautiful villa, very spacious, gorgeous property and great restaurant on the property to have a delicious meal. Staff very welcoming. Close to other main cities, like Siena, for day trips. We loved sitting by the pool, although it wasn’t heated, so too cold to use in April. We did love using the indoor heated pool and hot tub each day. We had a fabulous time and hope to go back someday! "
Canada
Jeremy
The price is ฿5,266
฿5,792 total
includes taxes & fees
16 May - 17 May
Villa di Sotto
Front of property

Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca
Loro Ciuffenna
9.8 out of 10, Exceptional, (35 reviews)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is ฿5,831
฿6,414 total
includes taxes & fees
17 May - 18 May
Relais Villa Belpoggio - Residenza d'Epoca
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (28 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
The price is ฿3,086
฿3,547 total
includes taxes & fees
13 May - 14 May
DormiVeglia B&B
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (36 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is ฿3,143
฿3,684 total
includes taxes & fees
20 May - 21 May
iConic Wellness Resort
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (23 reviews)
"Such a beautiful place to stay! The cottage was amazing, very spacious and clean. The grounds themselves were picturesque, was well above our expectations and the host was very welcoming and accommodating."
United Kingdom
Sasha
The price is ฿7,983
฿9,085 total
includes taxes & fees
13 May - 14 May
Borgo Argenina
Aerial view

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (65 reviews)
"Pros: 1. Beautiful property with an amazing view. 2. Spacious family suite 3. Comfortable bed 4. Quiet, waking up to birds singing in the morning. Cons: 1. Stink bugs in the suite; once we understood they are common this time of year and easy to capture and release outside, it was ok. 2. Showers are very small. 3. A/C not turned on this time of year; was not offered fans until the last day. 4. Minimal amenities. 5. Few outlets The villa is beautiful, just be prepared for a “rustic”...
United States
Niyo
The price is ฿5,291
฿6,124 total
includes taxes & fees
13 May - 14 May
Villa Curina Resort
8 outdoor pools

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is ฿27,948
฿31,046 total
includes taxes & fees
13 May - 14 May
Villa Marcolina
Front of property

Villa La Ginestra

Villa La Ginestra
Subbiano
9.6 out of 10, Exceptional, (5 reviews)
"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."
Canada
Philippe
The price is ฿4,357
฿4,793 total
includes taxes & fees
14 May - 15 May
Villa La Ginestra
Breakfast area

Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (20 reviews)
"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 ฿3,899
฿4,289 total
includes taxes & fees
18 May - 19 May
Locanda Antico Borgo
Exterior

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (13 reviews)
"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
The price is ฿5,369
฿6,210 total
includes taxes & fees
23 May - 24 May
L' Eroico
Courtyard

Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (5 reviews)
"Amazing stay at this hotel I would recommend it. Great hospitality, clean and picture postcard views. "
United Kingdom
Liam
The price is ฿9,962
฿11,035 total
includes taxes & fees
13 May - 14 May
Fontelunga Hotel & Villas
Front of property

Podere La Chiusella

Podere La Chiusella
Rapolano Terme
9.4 out of 10, Exceptional, (30 reviews)
"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
The price is ฿3,538
฿4,043 total
includes taxes & fees
14 May - 15 May
Podere La Chiusella
Seasonal outdoor pool

Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
The price is ฿7,515
฿8,456 total
includes taxes & fees
18 May - 19 May
Albergo Diffuso Borgo Santo
Cottage | Dining

Tuscan Style Apartment with View of the Hills

Tuscan Style Apartment with View of the Hills
Lucignano
The price is ฿10,384
฿11,536 total
includes taxes & fees
13 May - 14 May
Tuscan Style Apartment with View of the Hills
Property entrance

Castello di Modanella

Castello di Modanella
Rapolano Terme
7.8 out of 10, Good, (16 reviews)
"To far out"
United States
Dennis
The price is ฿3,074
฿4,672 total
includes taxes & fees
13 May - 14 May
Castello di Modanella
Porch

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (182 reviews)
"This property met all our needs for a one night stay. It is conveniently located near the train station and near the old town area. The people we encountered were friendly and helpful. The breakfast choices were plentiful and the breakfast area on the rooftop patio was beautiful. The only negative was that the walks of the room were thin and we could hear neighbors quite a bit. "
United States
Roger
The price is ฿3,008
฿3,538 total
includes taxes & fees
3 Jun - 4 Jun
Cameracaffè Centro
Exterior

San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is ฿4,761
฿5,389 total
includes taxes & fees
18 May - 19 May
San Michele al Borgo
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

Dievole Wine Resort

Dievole Wine Resort

10/10 Excellent
"Beautiful property and very friendly helpful staff"
Pamela 2-night trip
Posted 3 days ago
Dievole Wine Resort

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 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 an electric kettle. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Oliveto?

With 5 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. Sienese Gate and Arezzo Equestrian Centre 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.