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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Oliveto holiday rentals

Exterior

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is 2.247.800 ₫
2.534.549 ₫ total
includes taxes & fees
19 Apr - 20 Apr
Artisti del Cavallo Tourism
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (172 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is 3.422.401 ₫
3.857.595 ₫ total
includes taxes & fees
19 Apr - 20 Apr
Abbadia Sicille Relais
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 2.336.342 ₫
2.756.198 ₫ total
includes taxes & fees
4 May - 5 May
iConic Wellness Resort
Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers

Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (29 reviews)
"Lovely relaxation options and wonderful restaurant attached to the property! Great for a stay where you are travelling through Tuscany by car! Do not recommend travelling by public transport or taxi as it is very expensive."
Australia
Amelia
The price is 4.289.283 ₫
4.718.211 ₫ total
includes taxes & fees
19 Apr - 20 Apr
Villa di Sotto
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 2.256.250 ₫
3.535.354 ₫ total
includes taxes & fees
19 Apr - 20 Apr
Castello di Modanella
Front of property

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (64 reviews)
"Great stay but can feel a bit captive to their restaurant for dinner. Min 2 courses mandatory per person and dessert doesn’t count "
Canada
Shelley
The price is 4.753.054 ₫
5.476.237 ₫ total
includes taxes & fees
28 Apr - 29 Apr
Villa Curina Resort
Lobby

B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.6 out of 10, Exceptional, (21 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is 3.371.700 ₫
3.832.809 ₫ total
includes taxes & fees
20 Apr - 21 Apr
B&B Piccolo Hotel
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 4.284.340 ₫
4.712.774 ₫ total
includes taxes & fees
18 May - 19 May
Villa Cassia di Baccano
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 4.383.096 ₫
5.069.408 ₫ total
includes taxes & fees
27 Apr - 28 Apr
L' Eroico
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 3.075.485 ₫
3.507.181 ₫ total
includes taxes & fees
5 May - 6 May
San Michele al Borgo
Property grounds

Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Great time, perfect property and location."
United States
Christopher
The price is 6.459.929 ₫
7.230.070 ₫ total
includes taxes & fees
20 Apr - 21 Apr
Ca' Bianca Tuscany Relais
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 6.689.880 ₫
7.482.807 ₫ total
includes taxes & fees
27 Apr - 28 Apr
Castello di Gargonza
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (22 reviews)
"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "
United States
Massimo
The price is 4.932.062 ₫
5.673.564 ₫ total
includes taxes & fees
26 Apr - 27 Apr
Borgo Argenina
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 3.549.157 ₫
3.904.073 ₫ total
includes taxes & fees
20 Apr - 21 Apr
Villa La Ginestra
Cottage | Dining

Tuscan Style Apartment with View of the Hills

Tuscan Style Apartment with View of the Hills
Lucignano
The price is 6.372.073 ₫
7.102.234 ₫ total
includes taxes & fees
24 Apr - 25 Apr
Tuscan Style Apartment with View of the Hills
Deluxe Apartment, City View

CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is 4.824.919 ₫
5.400.522 ₫ total
includes taxes & fees
21 Apr - 22 Apr
CASA AMBRA
Exterior

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
The price is 6.234.349 ₫
6.950.738 ₫ total
includes taxes & fees
21 Apr - 22 Apr
Luxury resort in the Tuscan countryside
Apartment (1 Bedroom) | Front of property

Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is 2.765.526 ₫
3.166.017 ₫ total
includes taxes & fees
20 Apr - 21 Apr
Vicolo Della Scala Rooms - La Luna
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 2.545.832 ₫
2.924.563 ₫ total
includes taxes & fees
27 Apr - 28 Apr
DormiVeglia B&B
Exterior

Rocca di Castagnoli

Rocca di Castagnoli
Gaiole in Chianti
9.2 out of 10, Wonderful, (28 reviews)
"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 4.084.404 ₫
4.740.660 ₫ total
includes taxes & fees
30 Apr - 1 May
Rocca di Castagnoli
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"It was the nicest and most unique hotel stay and experience we’ve ever had! From the front desk staff to the restaurant and bar staff was beyond our expectations! The attention to detail from the cleaning staff and the spa was unbelievable! Hard to mention everyone. Every employees attention to detail makes this experience! The hotel is beyond stunning ! This hotel sets a high bar and absolutely met it with flying colours! "
James 3-night trip
Posted 18 hours ago
Monastero di Cortona Hotel & Spa

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.

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 San Luciano Winery 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.