San Simone Vacations from $1,453

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your San Simone Vacation

Lock in a San Simone vacation package and get set to experience the highlights of this city. Consider basing yourself in the neighborhood of Galatina Historic Centre, which is good for history, views and walking. Baia Verde Beach, Gallipoli Fish Market and Lido Conchiglie Beach are just some of the sights worth checking out during your trip to San Simone. That dream San Simone vacation is just a few clicks away. Browse flights, hotels and more on Expedia for an adventure that's tailored to suit your travel style.

The Latest San Simone vacation packages

Price found within the past 48 hours. Click for updated prices.
Montecallini Hotel - Adults Only
Marenea Suite Hotel - CDSHotels
Tenuta Montiró
ROBINSON APULIA - All Inclusive
Volito Hotel - Rural Experience
Don't see what you're looking for?
See all available trips from Columbus to San Simone
View all trips

San Simone Hotel Deals

Best Western Plus Leone di Messapia Hotel & Conference

Best Western Plus Leone di Messapia Hotel & Conference

4 out of 5
Provinciale Lecce Cavallino 32 Lecce LE
$124 nightly
The price is $146 total per night from Jun 9 to Jun 10
$146 total
Jun 9 - Jun 10
Total with taxes and fees
9.4/10 Exceptional! (155 reviews)
Clean room and quiet location. Property was very well maintained. Very helpful staff.

Reviewed on Nov 28, 2025

Best Western Plus Leone di Messapia Hotel & Conference
Le Dune Suite Hotel

Le Dune Suite Hotel

4 out of 5
Strada Dei Bacini 72 Porto Cesareo LE
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $147 total per night from May 15 to May 16
$147 total
May 15 - May 16
Total with taxes and fees
8.6/10 Excellent! (63 reviews)
Great hotel, with a beautiful private beach. Pool are was beautiful too. Really enjoyed our stay here.

Reviewed on May 2, 2026

Le Dune Suite Hotel
Arthotel & Park Lecce

Arthotel & Park Lecce

4 out of 5
Via Giorgio de Chirico, 1 Lecce LE
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $115 total per night from May 25 to May 26
$115 total
May 25 - May 26
Total with taxes and fees
8.4/10 Very Good! (172 reviews)
Staff member checking us in was unfamiliar with SERVICE dogs. That created a little friction, but was resolved. The room was comfortable, except for loud mechanical noises all night. The water pressure is excellent, but the shower is a bit small. The breakfast was adequate.

Reviewed on Apr 9, 2026

Arthotel & Park Lecce
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 Simone Vacation Packages

San Simone Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao

More vacations you might like

Frequently asked questions

How much does a San Simone vacation package cost?
Offering great value package deals from $1,453 on Expedia, you'll be thrilled with how little a vacation to San Simone costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to San Simone?
If you'd like to score a cheap San Simone vacation package, consider planning a trip in October, November and December. You'll typically find better prices on flights and accommodations during these quieter months — ideal for a budget-friendly break.
How many days is enough for San Simone?
With a well-organized itinerary, you can easily tick off the most popular San Simone sights in a handful of days. But if you'd like to discover lesser-known spots or go on day tours, think about booking your San Simone vacation for longer.
How to find the best San Simone package deals?
Finding a cheap San Simone package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly San Simone package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a San Simone vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays separately. Better still, you can personalize your San Simone trip to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to San Simone?
If you're considering an impromptu San Simone adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later San Simone vacation packages?
Your San Simone trip should be an escape from your busy life, not a reason for money-related stress. So to give you a little more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

Explore a world of travel with Expedia

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