Oliveto Holiday Rentals

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Holiday Rentals in Oliveto

Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
10.0 out of 10, Exceptional, 101 reviews
"Stephano goes out of his way to make his guests feel at home. The place was comfortable and spotless. We enjoyed getting to know our host and his city. The kitchen is well appointed with a well stocked wine rack. Read through the reviews, they are accurate! Comfortable bedding, lovely surroundings and, oh yes, a wonderful bakery across the street. Highly recommended!"
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Ultra Stunning 2 Br Apt In Tuscany, With Pool, Stoned Arch And Wooden Beams.
9.8 out of 10, Exceptional, 40 reviews
"Wow, wow, wow. This property delivered on so many fronts! It was even better than we anticipated. Next year we plan to stay here for 2 weeks. The view was spectacular, location was excellent. Lucia was a perfect host!"
Ultra Stunning 2 Br Apt In Tuscany, With Pool, Stoned Arch And Wooden Beams.
Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, 144 reviews
"It was good"
The price is NZ$241
includes taxes & fees
9 Jun - 10 Jun
Abbadia Sicille Relais
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Borgo Argiano
10.0 out of 10, Exceptional, 51 reviews
"Beautiful small hotel. We received a nice upgrade without asking for it. The apartments are very comfortable and has complete kitchens. They received us with a bottle of wine and some groceries. The hotel doesn't have a restaurant but there are some options nearby. I would only recommend staying here if you have a car. Good option to stay here and make day trips to different Tuscan towns."
Borgo Argiano
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.8 out of 10, Exceptional, 55 reviews
"Great comfortable apt. with spectacular terrace"
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Traditional stone cottage in rural, tranquil and quiet location built in 1799
10.0 out of 10, Exceptional, 31 reviews
"property and hosts were great. the drive down to it was an experience not to miss. you could hear a pin drop if it wasn't for the birds songs all day. thank you John and Diana for a brill time. 11 stars 🌟"
Traditional stone cottage in rural, tranquil and quiet location built in 1799
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
10.0 out of 10, Exceptional, 1 review
"Enjoyed it"
La Luna, Montefiorile, Gaiole in Chianti, Siena and Chianti
Il Poggio dell'Eremita
10.0 out of 10, Exceptional, 37 reviews
"The host was very welcoming upon arrival and gave us a great tour of the property along with some area history. Such a peaceful setting. Really enjoyed the patio upstairs off the bedroom. Great views of the terrain by day and fantastic views of the stars at night. Very close to the enchanting villages on hilltops nearby (Rigamagno and Scrofiano)."
Il Poggio dell'Eremita
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, 56 reviews
"Where to even begin? We loved everything about our stay. Stefania was wonderful, and responsive to our many questions before we even arrived. Upon arrival, it felt like a dream. The Villa is beautiful, private, and expansive. The property is huge, with lots of olive trees, fig trees, and places for the kids to play and explore. And not to mention the stunning pool, which overlooks the most incredible views of Cortona. We were pleased to find a ping pong table, and just absolutely loved the pool...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
10.0 out of 10, Exceptional, 38 reviews
"Montisi is a quaint village that is anywhere from 10 minutes to one hour drive to fabulous hill towns and wine tasting. The house is simple but charming. We spent most of our time while at the house by the pool, dining on the terrace and enjoying the beautiful views and sunsets. The kitchen is well appointed and with 4 women, we each enjoyed having our own bathroom. Luigi is a gracious host and provides excellent recommendations. I have every intention of returning! Thank you for a fabulous...
Montalcino: Private villa in the heart of Tuscany with private pool, Wi-fi
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
10.0 out of 10, Exceptional, 98 reviews
"We were group of 16 adults and three children under the age of three. Sonja and Diego could not have been better hosts! They are truly lovely people! Everything was absolutely perfect! The villa is stunning and very child friendly! We opted to have Sonja cook breakfast and dinner for us each day, and her food was absolutely delicious! You must try their pizza and bbq! We enjoyed the tennis court, feeding the horses, and day trips to Siena, Florence, and Montepulciano. The villa location is...
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
17th century farmhouse with private pool and Wi-Fi and air conditioning
9.4 out of 10, Exceptional, 32 reviews
"This property is located approx 5km from the beautiful town of Arezzo. There is a bus every hour, daily, from Tregozanno, where the property is actually located, to Arezzo. It is very rustic and in a beautiful setting. So relaxing. And, because it’s not right in town, the best of both worlds. There are no restaurants in Tregozanno but there is a great butcher and deli/mini market. There is also a pharmacy and bar! Maurizio, the owner lives next door and is the loveliest, most helpful human being...
17th century farmhouse with private pool and Wi-Fi and air conditioning
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
9.4 out of 10, Exceptional, 40 reviews
"Just on the slope nestled between Cortona city and the Calcinaio church, the location was perfect for us. We enjoyed the serenity of no one immediately around us while only being a very short drive from the city walls. (Admittedly, we could have walked, but driving was easier!) Taking day trips to various Tuscan cities and sights was wonderfully served by the central location."
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Podere Casorbica with free parking, large garden, swimming pool.
9.2 out of 10, Wonderful, 10 reviews
"We are a family of five and found the property ideal for our needs, the children occupied the first floor whilst mum and dad occupied the ground floor, both have a kitchen area and lovely bathrooms with ample space to dine together on the ground floor. The property was clean and is very well maintained. The owner Giorgio met us on our arrival and managed to answer any questions we had with the help of google translate and actually came to the property every morning to clean the pool, this was...
Podere Casorbica with free parking, large garden, swimming pool.
Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
9.6 out of 10, Exceptional, 14 reviews
"We enjoyed a lovely week in Val di Chiana in this beautiful remote spot. The hosts helped us to find the property when we first got there. The house is great. There were some issues with the water supply but they responded to the problem very promptly."
Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
9.8 out of 10, Exceptional, 90 reviews
"We had the most amazing time at Il Poggio! The property is well maintained, Roberta and Marina were incredible, and the location could not be beat. We took day trips (by car) to Siena, Arezzo, Florence, Orvieto, and Montalcino, all of which were easily and quickly accessible. Each of our five guests (two couples, one single!) had their own floor and bathroom. We cooked in the well-stocked kitchen, drank wine while watching the sunrise on the patio, and were transported to the past walking...
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Enchanting tuscan house, private garden, wellness, stunning views, easy to reach
10.0 out of 10, Exceptional, 14 reviews
"Our first trip to Tuscany. Casa Marta was absolutely located on the most gorgeous area of Val d’Orcia the views are as if you are looking at a painting. Carine is a fabulous host with great suggestions on where to visit and things to do in the surrounding villages. This was our first trip but not our last."
Enchanting tuscan house, private garden, wellness, stunning views, easy to reach
House consists of a "two-room" and a "trilocale", Valdarno Aretino
10.0 out of 10, Exceptional, 45 reviews
"This is a well contained villa with a beautiful garden surrounding the property. As a group of friends we enjoyed all the comforts of the property including the swimming pool. Spent relaxing times in the porch beside the kitchen. The bedrooms are well furnished and clean. The kitchen is well equipped. The hosts Santa and Giovanni are lovely and stocked the kitchen with complimentary essentials and drinks. They also provided some vegetables from their allotment which was very kind of them. We...
House consists of a "two-room" and a "trilocale", Valdarno Aretino
Idyllic guest house in Tuscan country house style with swimming pool
10.0 out of 10, Exceptional, 8 reviews
"The countryside on the way from the picturesque medieval town of Sinalunga, was spectacular and the surrounding countryside and villages were the prettiest we’ve ever seen. The housekeeper, Daniella, took care of all our needs on site and got us the house olive oil and wine when we requested to buy them. She was an absolute sweetheart with a warm heart and a smile as bright as the Tuscan sunrise."
Idyllic guest house in Tuscan country house style with swimming pool
Adorable house in charming Chianti hamlet btwn Siena, Arezzo and Florence
9.8 out of 10, Exceptional, 29 reviews
"Coming to Tuscany we were looking for a special place to stay just like we see in movies. Thanks to Gianna’s property we were able to discover the life under the Tuscan sun. The architecture of the house, the landscape, the flowers, and the view from the pool was just what we were looking for. It was so clean and felt great on a hot day. Our kids couldn’t get enough. Gianna took great attention to give us olive oil, wine, breakfast items, and homemade jam. The kitchen is fully equipped for...
Adorable house in charming Chianti hamlet btwn Siena, Arezzo and Florence
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See all available properties in Oliveto
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.

Other types of properties in Oliveto you may be interested in

La Certosa di Pontignano
9.4 out of 10, Exceptional, 312 reviews
"This BEAUTIFUL location in Tuscany is wonderful! I wish we had had time to stay longer! We ate in the courtyard for dinner and loved the restaurant as well. Convenient parking, breakfast and wifi included. This place is terrific!"
The price is NZ$192
includes taxes & fees
4 Jul - 5 Jul
La Certosa di Pontignano
Monastero di Cortona Hotel & Spa
5.0 star property
10.0 out of 10, Exceptional, 171 reviews
"What a beautiful place. Staff was amazing, so helpful in every way. Lovely breakfasts in the garden. Their bartender fixes some incredible cocktails and the one night we had dinner in the hotel restaurant, everything was delicious. A word of advice: If you’re driving, insist on a SMALL rental car. Cortona is full of tiny curvy cobblestone streets some of which you must drive through to get to and from the hotel. We were offered an upgrade to a Jeep with the turning radius of a semi truck and...
The price is NZ$546
includes taxes & fees
23 Jun - 24 Jun
Monastero di Cortona Hotel & Spa
Villa di Piazzano - Small Luxury Hotel of the World
5.0 star property
9.8 out of 10, Exceptional, 176 reviews
"This hotel is one of the best we have experienced. The setting is beautiful, the room was very nice, the food was the best we had in Italy (and beyond) and the service is impeccable. The entire staff is amazing, but we wanted to point out the extra efforts from Paolo, Davide and Mikelo. Now we know why we met several returning couples to this property. We will return as well!"
The price is NZ$910
includes taxes & fees
16 Jun - 17 Jun
Villa di Piazzano - Small Luxury Hotel of the World
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oliveto holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oliveto. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oliveto. Seeing all the best attractions is bound to make you fall in love with Oliveto. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oliveto short-term rentals, that won’t be hard to do.

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 Arezzo Equestrian Centre, or get outside and enjoy nature at Piazza Guido Monaco. Comune di Monte San Savino 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.

Recent reviews of Oliveto properties
Expedia verified reviews