San Simone Vacations from $830

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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.
Vinilia Wine Resort

Vinilia Wine Resort

4 out of 5
Price was $912, price is now $830 per person
$830
per person
Jan 26 - Jan 28
found 14 hours ago
Roundtrip non-stop flight included
New York (NYC) to Brindisi (BDS)
9.4/10 Exceptional! (84 reviews)
Blissful property. Stunning main building with beautiful pool and spa setting. Exceptional restaurant experience. Excellent service throughout our stay. We hope we can revisit one day.

Reviewed on Jul 2, 2025

Masseria dei Monaci

Masseria dei Monaci

4 out of 5
Price was $1,145, price is now $982 per person
$982
per person
Jan 12 - Jan 17
found 21 hours ago
Roundtrip flight included
New York (JFK) to Brindisi (BDS)
8.6/10 Excellent! (48 reviews)
We had a wonderful stay at this peaceful and beautifully restored masseria just outside Otranto. The setting is serene, surrounded by olive groves and close to the coast, with a perfect blend of rustic charm and modern comfort. One of the highlights of our visit was the fish set menu – fresh, flavourful and beautifully presented. The staff were warm and welcoming, and the whole experience felt authentically Salento. Highly recommended for anyone looking to unwind and enjoy the best of Puglia.

Reviewed on Oct 7, 2025

Le Dune Suite Hotel

Le Dune Suite Hotel

4 out of 5
Price was $1,017, price is now $882 per person
$882
per person
Jan 12 - Jan 17
found 21 hours ago
Roundtrip flight included
New York (JFK) to Brindisi (BDS)
8.6/10 Excellent! (57 reviews)
Perfect location for an excellent beach - with great amenities. Excellent half board package delivered a great dining experience. Within a reasonable walking distance to the town centre and the restaurants/bars/shopping/sights there. The whole hotel team went to great lengths to look after us and no ask was too much. Highly recommended.

Reviewed on Sep 22, 2025

Antica Masseria Martuccio

Antica Masseria Martuccio

4 out of 5
Price was $1,095, price is now $983 per person
$983
per person
Jan 12 - Jan 17
found 21 hours ago
Roundtrip flight included
New York (JFK) to Brindisi (BDS)
9.6/10 Exceptional! (84 reviews)
We enjoyed our vacation in this lovely accommodation. This place is perfect for relaxing getaway. Staff Is incredibly friendly!

Reviewed on Aug 17, 2025

Hotel Riva del Sole

Hotel Riva del Sole

4 out of 5
Price was $947, price is now $858 per person
$858
per person
Jan 12 - Jan 17
found 21 hours ago
Roundtrip flight included
New York (JFK) to Brindisi (BDS)
8/10 Very Good! (7 reviews)
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San Simone Hotel Deals

Grand Hotel di Lecce

Grand Hotel di Lecce

4 out of 5
Via Oronzo Quarta 28 Lecce LE
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $99 total per night from Dec 14 to Dec 15
$99 total
Dec 14 - Dec 15
Total with taxes and fees
8.2/10 Very Good! (303 reviews)
Wonderful stay
Breakfast was incredible and plentiful. Fresh fruit and vegetables with Salento products. Room was spacious but a bit outdated. However that is the style of the hotel. We could not use the pool due to bad weather but the pool area seemed nice.

Reviewed on Oct 2, 2025

Grand Hotel di Lecce
Directly on the beach. 6 beds in villa with private access to the sea

Directly on the beach. 6 beds in villa with private access to the sea

Scala di Furno Puglia
9.8/10 Exceptional! (43 reviews)
Well located property, so close to the lovely sandy beach. Clean and comfortable. Host Fabrizio was really helpful.

Reviewed on Sep 14, 2025

Get rates
Directly on the beach. 6 beds in villa with private access to the sea
Sangiorgio Resort & Spa

Sangiorgio Resort & Spa

5 out of 5
Prov.le Noha-Collepasso Cutrofiano LE
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $160 total per night from Dec 19 to Dec 20
$160 total
Dec 19 - Dec 20
Total with taxes and fees
9.4/10 Exceptional! (50 reviews)
This is a lovely hotel for relaxing & enjoying peace & tranquility of Salento The rooms are spacious lovely & super comfy beds & well cleaned every day The restaurant has a daily menu & food is great quality, my wife is Vegan and the staff & Chef made dinners for her every night!! The staff are absolutely ...

Reviewed on Sep 25, 2025

Sangiorgio Resort & Spa
See all 8,250 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

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Frequently asked questions

How much does a San Simone vacation package cost?
Offering great value package deals from $830 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.

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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.