Oliveto Vacations from $1,109
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Your Oliveto Vacation
With all your travel needs organized before you go, our Oliveto vacation packages let you simply focus on vacationing! One place to base yourself in this vibrant city is San Pancrazio, which is great for culture and walking. Ready to explore your new surroundings? Civitella Longobard Castle, Virgin Mary with Child and Praetorian Palace are just three of the top-rated places to visit during your trip to Oliveto. Your dream Oliveto vacation is a few clicks away. Browse hotels, flights and more on Expedia for a trip that's tailored to suit your style.
The Latest Oliveto vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Duomo Firenze
Historic Centre of Florence
$1,109
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
I can’t understand how the property even considers selling a room the size I was in under a staircase with a shower which barely trickles.
Reviewed on Sep 19, 2026
Aurum Firenze
Historic Centre of Florence
$1,233
per person
Oct 21 - Oct 27
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Breakfast was great. Our room was a little small but okay. Close to Mercato Centrale and Piazza del Duomo. Lots of great places to eat. Special mention to Trattoria Palle d’oro.
Reviewed on Sep 20, 2026
Grand Hotel Cavour
Historic Centre of Florence
$2,465
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,004 reviews)
Lovely hotel and great position in Florence. Staff were friendly and helpful. Breakfast was lovely plenty of choice. Wouldn’t hesitate to stay there again. Perfect for the usual sightseeing !
Reviewed on Sep 15, 2026
Aurum Uffizi
Historic Centre of Florence
$1,189
per person
Oct 22 - Oct 27
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,001 reviews)
We had a terrible stay. The first night there the air conditioner leaked and most of my clothes were soaked as my suitcase was on the beach under the air conditioner! When I brought it to their attention. And asked for help on drying my clothes, They didn’t seem to care! Shower was also cold! Also brought this to their attention and again didn’t care. I asked for a small compensation for the inconvenience and they said no!!! None of my what’s app messages were answered!! My whole stay was awful! I would not recommend !
Reviewed on Sep 20, 2026
What to do in Oliveto
Arezzo: Val di Chiana Wine Tasting Experience
$47
per adult
Oliveto Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
$635 nightly
$708 total
Oct 19 - Oct 20
Total with taxes and fees
9.8/10 Exceptional! (250 reviews)
"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"
Reviewed on Sep 20, 2026
La Certosa di Pontignano
loc. Pontignano, 5 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
$91 nightly
$110 total
Oct 5 - Oct 6
Total with taxes and fees
9.4/10 Exceptional! (564 reviews)
"Magical place! We loved jazz night and the amazing wine paired dinner. Fantastic place!"
Reviewed on Sep 16, 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
$361 nightly
$406 total
Oct 11 - Oct 12
Total with taxes and fees
10/10 Exceptional! (335 reviews)
"There was nothing to be improved because everything was perfection!!"
Reviewed on Sep 19, 2026
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.
Find the Best Oliveto Vacation Packages
Oliveto Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Max Temp Winter | 45ºF |
Max Temp Summer | 80ºF |
Top Sights | Civitella Longobard Castle, Church of Santa Maria Assunta and Buriano Bridge and Penna Natural Reserve |
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Frequently asked questions
How much does an Oliveto vacation package cost?
You'll find cheap prices from $1,109 on Expedia for your Oliveto getaway. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Oliveto costs.
What are the cheapest months to go to Oliveto?
November, December and January are great times to look for cheap Oliveto vacation packages. Opting to travel in quieter months means you can usually find lower prices on flights and accommodations.
How many days is enough for Oliveto?
The ideal duration for your Oliveto vacation depends on what you'd like to do and see. Typically, a few days to a week will give you enough time to go to all the leading sights and discover some hidden gems along the way.
How to find the best Oliveto package deals?
Start your search for an Oliveto package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Oliveto package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Oliveto getaway off to a flying start.
Is it cheaper to book an Oliveto vacation as a package?
You can enjoy significant savings on your Oliveto getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to view the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Oliveto?
If you have your Oliveto travel dates locked in, book as early as you can to score some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Oliveto vacation packages?
Secure your perfect escape to Oliveto with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until your next payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stay on budget and snap up cheap deals while they last.
Explore a world of travel with Expedia
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- Visit Marciano della Chiana
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- Visit Badia Agnano
- Piazza Grande
- Visit Viciomaggio
- Comune di Monte San Savino
- Valdichiana Outlet Village
- Terme Antica Querciolaia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
