San Leonardo Vacations from $858

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Your San Leonardo Vacation

There's plenty to like about San Leonardo, from its rural countryside to its spectacular views and beyond. When you're ready to say hello to this lively city, our San Leonardo vacation packages will be perfect for you. You'll want to go sightseeing during your trip to San Leonardo. Don't miss major attractions such as Riserva Naturale dello Stagnone, Spiaggia di San Teodoro and Donnafugata Winery. Expedia will help you escape your daily routine. Tailor your vacation to San Leonardo to suit your travel style, whatever that may look like.

The Latest San Leonardo vacation packages

Price found within the past 48 hours. Click for updated prices.
Tenute Baglio Passofondo

Tenute Baglio Passofondo

$858
per person
Dec 2 - Dec 4
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Palermo (PMO)
9/10 Wonderful! (12 reviews)
The only flaws are that the rooms are very small, the air conditioner did not function properly on a hot day and this place is in the middle of nowhere. If you are seeking exclusive this is it

Reviewed on Sep 17, 2026

Porta di Castro Hotel & Spa

Porta di Castro Hotel & Spa

Palermo Historical Center
$1,472
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Palermo (PMO)
9.4/10 Exceptional! (489 reviews)
We loved this little gem of a place with lots of character. The staff are super nice and speak good English - they arranged airport pickup and late check-in flawlessly and helped us find a restaurant 2 mins away still open with delicious food when we arrived. Our room was very comfortable and pretty, the bathroom small but modern, the breakfast was wonderful with lots of options and the pool/hot tub area was divine to relax in after a hot day sightseeing. The location in old town was convenient for walking. Everything worked well including aircon.

Reviewed on Oct 14, 2026

Grand Hotel et Des Palmes

Grand Hotel et Des Palmes

Politeama
$1,776
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Palermo (PMO)
8.4/10 Very Good! (1,002 reviews)
Massimo Plaza Hotel

Massimo Plaza Hotel

Palermo Historical Center
$1,441
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Palermo (PMO)
9/10 Wonderful! (356 reviews)
Loved our stay at massimo. In a greatly location, right across from the opera house. Great bfast provided each morning. Good, clean room of good size. Staff very accommodating. The entire place is older and could use a refresh but very clean. I would recommend to anyone looking for a wonderful place in great location

Reviewed on Oct 14, 2026

Bellaroto Suite & Spa - Charming Boutique Rooms

Bellaroto Suite & Spa - Charming Boutique Rooms

Palermo Historical Center
$1,358
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Palermo (PMO)
9.6/10 Exceptional! (117 reviews)
Uniquely charming old Palazzo ideally located within a few minutes walk of many Palermo attractions. Small common area is just outside the rooms, a good place to enjoy tea, coffee, fruit and biscuits, and to meet other guests. Good restaurant suggestions. Room quiet despite busy neighborhood. Older or less able guests need to know that access is possible only via outside staircase, expect no help with bags.

Reviewed on Sep 21, 2026

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Stay near popular San Leonardo attractions

Ettore and Infersa Salt Museum

10.0/10 (4 reviews)
You can browse the exhibits at Ettore and Infersa Salt Museum, a museum with a story of its own, during your travels to San Leonardo. Stroll along the area's seaside or simply enjoy its wineries.
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What to do in San Leonardo

From Trapani: Favignana & Levanzo Full Day Boat Tour

From Trapani: Favignana & Levanzo Full Day Boat Tour

$116
per adult
80% of travellers recommend
From Trapani: Favignana & Levanzo Full Day Boat Tour
Marsala: Winery Tour with Wine Tasting and Local Products

Marsala: Winery Tour with Wine Tasting and Local Products

$26
per adult
100% of travellers recommend
Marsala: Winery Tour with Wine Tasting and Local Products
From Trapani: Aegadian Islands Boat Tour to Favignana and Levanzo with Lunch

From Trapani: Aegadian Islands Boat Tour to Favignana and Levanzo with Lunch

$115
per adult
From Trapani: Aegadian Islands Boat Tour to Favignana and Levanzo with Lunch
See all activities in San Leonardo

San Leonardo Hotel Deals

SEAWATER HOTEL BIO & BEAUTY SPA

SEAWATER HOTEL BIO & BEAUTY SPA

Via Trapani 330 Marsala TP
$55 nightly
$67 total
Oct 20 - Oct 21
Total with taxes and fees
SEAWATER HOTEL BIO & BEAUTY SPA
 Phi Hotel La Tonnara di Bonagia

Phi Hotel La Tonnara di Bonagia

Piazza Tonnara Valderice TP
Fully refundableReserve now, pay when you stay
$155 nightly
$177 total
Oct 29 - Oct 30
Total with taxes and fees
Phi Hotel La Tonnara di Bonagia
Almar Giardino di Costanza Mazara del Vallo Resort & Spa

Almar Giardino di Costanza Mazara del Vallo Resort & Spa

Via Salemi 100, Km 7 Mazara del Vallo TP
$229 nightly
$259 total
Oct 18 - Oct 19
Total with taxes and fees
9.4/10 Exceptional! (179 reviews)
"Nice hotel and spa. Staff was helpful. Misleading information about being on the beach when in reality it is in the middle of nowhere."

Reviewed on Oct 12, 2026

Almar Giardino di Costanza Mazara del Vallo Resort & Spa
See all 1,918 properties in San Leonardo
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 Leonardo Vacation Packages

San Leonardo Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Vicenzo Florio Airport (TPS)
Max Temp Winter
60ºF
Max Temp Summer
80ºF
Top Sights
Spiaggia di San Teodoro, Donnafugata Winery and Marco De Bartoli - Samperi

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Frequently asked questions

How much does a San Leonardo vacation package cost?
Offering great value package deals from $858 on Expedia, you'll be pleasantly surprised at how much a vacation to San Leonardo costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to San Leonardo?
If you're looking to score a cheap San Leonardo vacation package, consider planning a trip in November, December and January. You'll generally find lower prices on accommodations and flights during these months — ideal for a budget-friendly getaway.
How many days is enough for San Leonardo?
The ideal duration for your San Leonardo vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you plenty of time to check out all the leading sights and discover some hidden treasures along the way.
How to find the best San Leonardo package deals?
Use Expedia's filter tool to find some great San Leonardo package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for San Leonardo package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a San Leonardo vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and stays separately. Better still, you can customize your San Leonardo trip to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to San Leonardo?
If you have your San Leonardo travel dates confirmed, book as early as you can to snap up some awesome deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for traveling on a whim.
How to plan a trip to San Leonardo?
  1. Choose when to go: Check your schedule and pack your bags. Your favorite season and the available activities will also help you decide when to vacation in San Leonardo.
  2. Plan your budget wisely: As well as the price of your hotel, you'll need to factor in other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to San Leonardo.
  3. Organize your San Leonardo getaway with our trip planning tool: Search for and book accommodations and experiences all in one place. You can also collaborate with family and friends to plan an unforgettable trip to San Leonardo together.
  4. Decide your trip length: Consider how long you want to spend discovering San Leonardo. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  5. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose a San Leonardo vacation package that brings all your bookings together.
  6. Book any day trips or activities: Now to the fun part — locking in everything you want to do and see. Explore some of the incredible things to do in San Leonardo and reserve your tickets early to save time (and maybe some spending money too!).
Does Expedia offer Book Now, Pay Later San Leonardo vacation packages?
Your San Leonardo break should be a relaxing escape from your daily routine, not a source of money-related stress. So to allow you extra flexibility, we've partnered with online lender Affirm to offer 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 aren't any hidden costs or late payment fees to worry about.

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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.