San Simone Vacations from $1,290

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.
Città Bianca Country Resort

Città Bianca Country Resort

4 out of 5
Price was $1,396, price is now $1,290 per person
$1,290
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Brindisi (BDS)
7.6/10 Good! (66 reviews)

Hotel Del Levante

Hotel Del Levante

4 out of 5
Price was $2,147, price is now $1,743 per person
$1,743
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Brindisi (BDS)
7.8/10 Good! (59 reviews)
The ocean is in front of the hotel with umbrellas & chase lounge chairs available! Life guard in attendance. Free “delicious “ breakfast! Lunch & dinner were excellent. Close ( 6 minutes ) to Torre Canne ( lighthouse) and the staff is professional

Reviewed on Jun 29, 2026

Borgo Canonica

Borgo Canonica

4 out of 5
Price was $1,943, price is now $1,744 per person
$1,744
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Brindisi (BDS)
9.8/10 Exceptional! (167 reviews)
Absolutely gorgeous, well managed property. Beautiful suite in a stone trullo, and we enjoyed the infinity pool, excellent dinner and breakfast in a stunning setting surrounded by olive groves. So peaceful and relaxing. An oasis! Did not want to leave.

Reviewed on Jun 21, 2026

Granserena Hotel

Granserena Hotel

4 out of 5
Price was $1,969, price is now $1,816 per person
$1,816
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Brindisi (BDS)
7.8/10 Good! (25 reviews)
The super friendly and efficient staff make this place a wonderful choice for families with kids of all ages. From reception to the team running the entertainment, the chefs and the house-keeping staff are a wonderful hard working team . The location is perfect for children and families.

Reviewed on Jul 10, 2026

Masseria Malvindi

Masseria Malvindi

5 out of 5
Price was $1,657, price is now $1,540 per person
$1,540
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Brindisi (BDS)
9.4/10 Exceptional! (40 reviews)
Perfect all around. Lovely staff too

Reviewed on Jun 29, 2026

Don't see what you're looking for?
See all available trips from Columbus to San Simone
View all trips

San Simone Hotel Deals

Arthotel & Park Lecce

Arthotel & Park Lecce

4 out of 5
Via Giorgio de Chirico, 1 Lecce LE
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $136 total per night from Aug 6 to Aug 7
$136 total
Aug 6 - Aug 7
Total with taxes and fees
8.4/10 Very Good! (174 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
CDSHotels Grand Hotel Riviera

CDSHotels Grand Hotel Riviera

4 out of 5
Via Emanuele Filiberto n.172/174 Nardò LE
$223 nightly
The price is $255 total per night from Jul 19 to Jul 20
$255 total
Jul 19 - Jul 20
Total with taxes and fees
9/10 Wonderful! (102 reviews)
"The view of the sea was spectacular. The entire property and room were in excellent condition and very clean. The daily breakfast was amazing and the terrace cookout was superb, especially the wine. Each employee went went above and beyond, from front desk, dining staff to housekeeping."

Reviewed on Jul 1, 2026

CDSHotels Grand Hotel Riviera
Relais Corte Palmieri

Relais Corte Palmieri

4 out of 5
Corte Palmieri, 3 Gallipoli LE
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $182 total per night from Jul 15 to Jul 16
$182 total
Jul 15 - Jul 16
Total with taxes and fees
9/10 Wonderful! (268 reviews)
"Great location in historical centre. Staff very helpful and professional. Lovely seating area around plunge pool with views across the city and coastline. Enjoyable breakfast in a very pleasant setting."

Reviewed on Jun 28, 2026

Relais Corte Palmieri
See all 8,688 properties in San Simone
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

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a San Simone vacation package cost?
Offering great value package deals from $1,290 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.