South Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top South Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Conch Club Cottage

Conch Club Cottage

2 out of 5
Price was CA $3,077, price is now CA $2,147 per person
CA $2,147
per person
Jan 6 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Little Cayman (LYB)
10/10 Exceptional! (7 reviews)
Very nice, recently remodeled, bright and clean.

Reviewed on Apr 7, 2026

Le Soleil d'Or CaymanBrac

Le Soleil d'Or CaymanBrac

3.5 out of 5
Price was CA $3,120, price is now CA $2,389 per person
CA $2,389
per person
Jan 6 - Jan 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to West End (CYB)
9.2/10 Wonderful! (20 reviews)

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South Side Hotel Deals

Le Soleil d'Or CaymanBrac

Le Soleil d'Or CaymanBrac

3.5 out of 5
2147 South Side Road West End
Fully refundableReserve now, pay when you stay
The price is CA $536 per night from Dec 2 to Dec 3
CA $536
CA $748 total
Dec 2 - Dec 3
includes taxes & fees
Le Soleil d'Or CaymanBrac
Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!

Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!

Cayman Brac Sister Islands
10/10 Exceptional! (10 reviews)
"The hammocks are wonderful. Dennis was very good with communication. This was our third time staying at Blue Karma."

Reviewed on Jun 7, 2026

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Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!
West End Cayman Brac Ocean front with pool at Carib Sands

West End Cayman Brac Ocean front with pool at Carib Sands

Cayman Brac Cayman Islands
10/10 Exceptional! (4 reviews)
"Our stay at Stumble Inn was fantastic! Karen is a great host, very responsive to questions and she was super accommodating when we needed to make date changes. She was helpful with suggestions regarding car rental, dive shops, restaurants and bars. The condo was clean and well-stocked with basics ..."

Reviewed on May 31, 2026

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West End Cayman Brac Ocean front with pool at Carib Sands
See all 78 properties in South Side
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.
All Inclusive Vacations
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Beach Vacations
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Stay near popular South Side attractions

Cayman Brac Lighthouse

8.8/10 (3 reviews)
You can learn about the history of East End with a visit to Cayman Brac Lighthouse. Amble around this relaxing area's beaches, or seek out the snorkeling spots.
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Frequently asked questions

How much does a South Side vacation package cost?
Perhaps less than you might think — from as low as CA $2,147, in fact! By combining hotels, flights and car rentals into a custom-made travel package, your trip to South Side is only clicks away.
How do I get a cheap travel package to South Side?
Simply by bundling. Flights, rental cars and hotels — combine whatever you need into a South Side vacation package to save tons of cash. Score even more bargains when you add extras such as activities or tours to your booking. But that's not the only impressive part. You have the freedom to customize your trip your way. We offer more than 550 partner airlines and 1,000,000 hotels globally, so that everyone has an opportunity to travel and fulfill those vacation dreams.
What are the top hotels in South Side?
Oceanfront Villa - Charming, Romantic and The Alexander #101 - Queen Suite are a couple of great places to stay in East End. A must-do on any good South Side itinerary, we recommend taking the time to fully explore this impressive city.
How far in advance should I book my South Side vacation?
Earlier is always better. Airlines generally release flights nearly 12 months in advance, and this is when you can land some of the lowest prices. Boss just told you to take all your vacation days next week? No need to worry. Expedia are never short on fantastic bargains to send you off on the getaway of your dreams, at an affordable price.
What does an Expedia South Side travel package include?
Packages include hotels, rental cars and flights, but you can mix and match them to create your ideal South Side vacation. You can also add on some activities and experiences once you've made your booking. You're the boss! When you bundle your bookings with Expedia, you'll score deals you won't find elsewhere.
Can I choose my airline with a South Side Expedia vacation package?
Yes, you sure can. We offer more than 550 partner airlines worldwide, so go with the carrier that suits your budget needs.
If I'm not able to travel, can I cancel my South Side vacation package?
It is possible to cancel your South Side booking if your travel plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.