San Leo Vacation Packages

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Your San Leo Vacation

Let our vacation packages to San Leo inspire your next getaway. There's loads to like about this interesting city, starting with the neighborhood of Montegrimano, which is good for nature and views. Eager to start exploring your surroundings? Fortress of San Leo, Montebello Castle and Rocca del Sasso are some of the best places to visit during your trip to San Leo. Browse Expedia's extensive range of travel options and start organizing your ideal vacation to San Leo today.

Top San Leo Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Social Hub Bologna

The Social Hub Bologna

4 out of 5
Bologna Fiere District
per person
Sep 14 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bologna (BLQ)
9/10 Wonderful! (492 reviews)
Very close to Bolonia central station

Reviewed on Jul. 28, 2025

Hotel Select Suites & Spa / Apartments

Hotel Select Suites & Spa / Apartments

4 out of 5
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bologna (BLQ)
9/10 Wonderful! (134 reviews)
Hotel Stella

Hotel Stella

3.5 out of 5
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bologna (BLQ)
8.6/10 Excellent! (31 reviews)
Hotel Zeus

Hotel Zeus

3 out of 5
Viserbella
per person
Sep 4 - Sep 9
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Bologna (BLQ)
10/10 Exceptional! (3 reviews)
Hotel Club House

Hotel Club House

4 out of 5
Marina Centro
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Bologna (BLQ)
8.6/10 Excellent! (144 reviews)
This was a wonderful place to stay right on the beach. The room balcony overlooked the seea and sand. I will be coming back next summer to stay again.

Reviewed on Jun. 7, 2025

Ready to book your vacation to San Leo?

 

Choose your dates

San Leo Hotel Deals

c-hotels International

c-hotels International

3 out of 5
Viale Modena 19, Cattolica, RN
Fully refundableReserve now, pay when you stay
The price is CA $53 per night from Jul 31 to Aug 1
CA $53
CA $64 total
Jul 31 - Aug 1
includes taxes & fees
8.2/10 Very Good! (85 reviews)
Lovely, Clean Hotel
"This hotel is a great find, it's well priced, great location and it is IMMACULATE, fresh towels everyday, bed made and room cleaned everyday. Staff were very friendly and accommodating, I would definitely return here! You get what you pay for in most places, however this hotel exceeded my expectations ..."

Reviewed on Jun. 25, 2025

c-hotels International
HOTEL YOUNG PEOPLE UNDER 40

HOTEL YOUNG PEOPLE UNDER 40

Viale Regina Elena 253, Rimini, RN
The price is CA $55 per night from Jul 29 to Jul 30
CA $55
CA $69 total
Jul 29 - Jul 30
includes taxes & fees
6.2/10 (9 reviews)
"Grazie molto"

Reviewed on Jun. 15, 2025

HOTEL YOUNG PEOPLE UNDER 40
Hotel Avana Mare

Hotel Avana Mare

3 out of 5
Viale Gaetano Genghini, Rimini, RN
Fully refundableReserve now, pay when you stay
The price is CA $71 per night from Jul 31 to Aug 1
CA $71
CA $86 total
Jul 31 - Aug 1
includes taxes & fees
7.8/10 Good! (124 reviews)
"Staff were very helpful & friendly. Quiet area & a stones throw from the beach"

Reviewed on May 17, 2025

Hotel Avana Mare
See all 2,742 properties in San Leo
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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What to do in San Leo

San Leo Cashmere: Farm Experience

San Leo Cashmere: Farm Experience

CA $78
per adult
San Leo Cashmere: Farm Experience
FORTRESS AT SUNSET

San Leo: Entrance ticket to the fortress and prison of Cagliostro

CA $18
per adult
San Leo: Entrance ticket to the fortress and prison of Cagliostro
See all activities in San Leo

Frequently asked questions

How much does a San Leo vacation package cost?
You'll find cheap prices from CA $1,384 on Expedia for your San Leo break. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to San Leo costs.
What are the cheapest months to go to San Leo?
Plan your trip for the off-peak season and you're likely to find cheap San Leo vacation packages. Keep in mind that public holidays and local festivals and events can impact prices, so do your research before you go.
How many days is enough for San Leo?
With a well-organized itinerary, you can easily tick off the top San Leo sights in a handful of days. But if you prefer to discover hidden spots or go on day tours, think about booking your San Leo vacation for longer.
Is it worth booking a vacation package to San Leo?
San Leo has everything you need for an amazing trip. Get your San Leo vacation off to a flying start by exploring major attractions like Cathedral of San Leo.
How to find the best San Leo package deals?
Begin your search for a San Leo package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect San Leo package deal right away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your San Leo adventure off to a flying start.
Is it cheaper to book a San Leo vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking hotels and flights separately. Better still, you can personalize your San Leo escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to San Leo?
Land incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu San Leo break.
How to plan a trip to San Leo?

  1. Pick your dates: The things you'd like to do in San Leo and your favourite season will help you decide when to get away.
  2. Budget wisely: As well as the cost of your stay, you'll need to factor in other expenses. These include food, transportation and flights. Also, set aside a little extra for unexpected costs that could crop up during your trip to San Leo.
  3. Decide how long to go for: Now that you're more familiar with San Leo, you can figure out the ideal length of your vacation. Create a draft plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a tailored San Leo vacation package.

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