Oliveto Vacations from $654

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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.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $951, price is now $654 per person
$654
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,007 reviews)
Breakfast was excellent

Reviewed on Sep 29, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,001, price is now $673 per person
$673
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,008 reviews)
Very centrally located, was able to walk everywhere. Is a bit loud until about 10:30 pm but after that it was fine. Room is comfortable and has everything you need especially if you are planning on being out most of the time.

Reviewed on Oct 13, 2025

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was $1,205, price is now $874 per person
$874
per person
Nov 17 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9/10 Wonderful! (1,005 reviews)
Great location, right next to the Duomo with a view from the terrace. Helpful staff, lead by Leone! Ice cream, coffee, breakfast snacks a nice touch and really appreciated having an elevator. Clean and comfortable, the only suggestion would be improved seating in the room. All told a very enjoyable stay.

Reviewed on Oct 10, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $1,859, price is now $1,351 per person
$1,351
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (477 reviews)
This is a beautiful hotel.It is spotlessly clean.The staff are friendly and helpful. Breakfast exceeded our expectations. The choice of food and service were excellent. It’s a good location to see the sights and get to the train station to visit Pissa etc. We will definitely book here for our next visit.

Reviewed on Oct 11, 2025

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $2,449, price is now $1,783 per person
$1,783
per person
Dec 28 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
8.6/10 Excellent! (472 reviews)
Great little hotel. Everything is within walking distance. The view from the terrace was amazing.

Reviewed on Aug 6, 2025

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Discover the most popular places to visit in Oliveto

Buriano Bridge and Penna Natural Reserve

Explore the great outdoors at Buriano Bridge and Penna Natural Reserve, a lovely green space in Civitella in Val di Chiana. Discover the countryside while you're in the area.

Buriano Bridge and Penna Natural Reserve

Virgin Mary with Child

You can learn about the history of Civitella in Val di Chiana when you stop by Virgin Mary with Child. Discover the area's countryside and wineries.

Virgin Mary with Child

Church of Santa Maria Assunta

After visiting Church of Santa Maria Assunta, make a plan to see the other sights and activities in Civitella in Val di Chiana. Discover the area's countryside and wineries.

Church of Santa Maria Assunta

What to do in Oliveto

Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

$23
per adult
Oil museum and oil mill in Tuscany: tour and tasting
The Villa

Cellar Tour & Wine Tasting

$58
per adult
Cellar Tour & Wine Tasting
WELCOME!

Private visit to the House of Grand Duke Leopold of Tuscany with invitation

$47
per adult
Private visit to the House of Grand Duke Leopold of Tuscany with invitation
See all activities in Oliveto

Oliveto Hotel Deals

A Point Arezzo Park Hotel

A Point Arezzo Park Hotel

4 out of 5
Loc. Battifolle, 36/T, A1 exit Arezzo, Arezzo, AR
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $123 total per night from Oct 20 to Oct 21
$123 total
Oct 20 - Oct 21
Total with taxes and fees
7.6/10 Good! (145 reviews)
Meh
"This hotel has so much potential, but many details are missing. From music to create a pleasant atmosphere in the communal areas, especially restaurant and breakfast space. (So awkward to hear everyone chew their food around you and the kitchen staff comments in the background) To electrical jobs ..."

Reviewed on Jul 3, 2025

A Point Arezzo Park Hotel
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore, Cortona, AR
Fully refundableReserve now, pay when you stay
$263 nightly
The price is $294 total per night from Nov 2 to Nov 3
$294 total
Nov 2 - Nov 3
Total with taxes and fees
9.8/10 Exceptional! (243 reviews)
"fabulous hotel with the most beautiful aperol spritz I have ever had served by the pool, and that was only one of the wonderful things I have to say about this beautiful hotel. The staff were helpful and accomodating, breakfast in the courtyard outstanding and our room was divine. Cant recommend ..."

Reviewed on Oct 9, 2025

Monastero di Cortona Hotel & Spa
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Via Spaltenna 13, Gaiole in Chianti, SI
$371 nightly
The price is $419 total per night from Oct 26 to Oct 27
$419 total
Oct 26 - Oct 27
Total with taxes and fees
9.4/10 Exceptional! (256 reviews)
"An incredible stay for anyone who wants to disconnect in pure luxury. Pure beauty and a very detailed luxury hotel."

Reviewed on Oct 9, 2025

Castello di Spaltenna- Small Luxury Hotels of the World
See all 5,125 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.

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 $654 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.