San Leo Vacations from $637

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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.

The Latest San Leo vacation packages

Price found within the past 48 hours. Click for updated prices.
HOTEL NOIR

HOTEL NOIR

4 out of 5
Save 100% on your flight
per person
Sep 2 - Sep 7
found 4 hours ago
Roundtrip non-stop flight included
London (LHR) to Bologna (BLQ)
7.6/10 Good! (4 reviews)
I got an excellent rate for the time I was there. The hotel staff were very service oriented and they had a great offer on for breakfast and lunch. Within 3 min walk of the beach.

Reviewed on Jul 5, 2025

Hotel Miramare

Hotel Miramare

4 out of 5
Save 100% on your flight
per person
Sep 2 - Sep 7
found 4 hours ago
Roundtrip non-stop flight included
London (LHR) to Bologna (BLQ)
7/10 Good! (85 reviews)
Smy Bologna Centrale

Smy Bologna Centrale

4 out of 5
Santo Stefano
Save 100% on your flight
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
London (LHR) to Bologna (BLQ)
7.6/10 Good! (460 reviews)
Less than a 10 minute walk from Centrale train station and centrally located for sightseeing. Quick check in process and all staff were friendly and knowledgeable with any questions we had.

Reviewed on Mar 22, 2025

Hotel Club House

Hotel Club House

4 out of 5
Marina Centro
per person
Sep 2 - Sep 7
found 4 hours ago
Roundtrip non-stop flight included
London (LHR) to Bologna (BLQ)
8.6/10 Excellent! (143 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

MarePineta Resort

MarePineta Resort

5 out of 5
Save 100% on your flight
per person
Sep 2 - Sep 7
found 4 hours ago
Roundtrip non-stop flight included
London (LHR) to Bologna (BLQ)
8.4/10 Very Good! (63 reviews)
Great experience! Will be coming back

Reviewed on Oct 5, 2024

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Discover the most popular places to visit in San Leo

Fortress of San Leo

Fortress of San Leo

Learn about the local history of San Leo when you take a trip to Fortress of San Leo. Discover the mountain views while you're in the area.

Fortress of San Leo

Cathedral of San Leo

You can learn about the history of San Leo with a stop at Cathedral of San Leo. Discover the mountain views while you're in the area.

Cathedral of San Leo

What to do in San Leo

San Leo Cashmere: Farm Experience

San Leo Cashmere: Farm Experience

$56
per adult
San Leo Cashmere: Farm Experience
FORTRESS AT SUNSET

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

$13
per adult
San Leo: Entrance ticket to the fortress and prison of Cagliostro
See all activities in San Leo

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
$43 nightly
The price is $52 total per night from Jul 9 to Jul 10
$52 total
Jul 9 - Jul 10
Total includes taxes and fees
8.2/10 Very Good! (81 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
$41 nightly
The price is $51 total per night from Jul 11 to Jul 12
$51 total
Jul 11 - Jul 12
Total includes taxes and fees
6/10 (8 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
7.8/10 Good! (124 reviews)
"Staff were very helpful & friendly. Quiet area & a stones throw from the beach"

Reviewed on May 17, 2025

Get rates
Hotel Avana Mare
See all 2,747 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.

Find the Best San Leo Vacation Packages

San Leo Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Federico Fellini Intl. Airport (RMI)
Population
200
Max Temp Winter
50ºF
Max Temp Summer
80ºF
Top Sights
Montebello Castle, Skypark Parco Avventura and Grotte di Onferno

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Frequently asked questions

How much does a San Leo vacation package cost?
You'll find cheap prices from $637 on Expedia for your San Leo escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to San Leo costs.
What are the cheapest months to go to San Leo?
You're likely to find reduced prices and greater availability in November, December and January. Explore our cheap San Leo vacation packages and you could land some excellent off-season deals.
How many days is enough for San Leo?
With a well-organized travel plan, you can easily tick off the top San Leo sights in a few days. But if you'd like 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 is a good vacation destination with attractions like Fortress of San Leo among the many things to keep you busy. Whether you're traveling with the family or planning a trip with friends, a San Leo vacation promises a good time for everyone.
How to find the best San Leo package deals?
Start your search for a San Leo package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal San Leo package deal straight away, simply tweak 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 underway.
Is it cheaper to book a San Leo vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels individually. Better still, you can tailor your San Leo trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to San Leo?
If you're considering a spontaneous San Leo adventure, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to San Leo?

  1. Choose when to get away: Check your diary and get your bags packed. Your favorite season and the activities on offer will also help you decide when to escape to San Leo.
  2. Plan your budget wisely: Besides the price of your hotel, you'll need to consider other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that could crop up during your trip to San Leo.
  3. Explore San Leo using Expedia's trip planning tool: Gain insights into the top attractions and best hotels for your trip to San Leo. You can also save your favorite locations, collaborate with family and friends and manage all your plans in one place.
  4. Decide how many days away: Start by making a list of all the activities and attractions you'd like to get to in San Leo. Then, estimate how long you'll need at each, including any travel time.
  5. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a San Leo vacation package that brings all your bookings together.
  6. Book activities and experiences in advance: Whether it's a ticket to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of San Leo. Find all the fun things to do in San Leo with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later San Leo vacation packages?
Your San Leo getaway is meant to be a relaxing escape from your daily routine, not a reason for money worries. So to allow you extra flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.