South Side Vacation Packages

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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 $2,502, price is now CA $1,812 per person
CA $1,812
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Little Cayman (LYB)
10/10 Exceptional! (7 reviews)
Adorable tiny cottage with modern amenities, direct access to pool and beach. Place was clean equipped with everything needed for a short stay. The beds were not very comfortable but we still enjoyed our stay very much and would stay again any day of the week!

Reviewed on Nov 4, 2025

Le Soleil d'Or CaymanBrac

Le Soleil d'Or CaymanBrac

3.5 out of 5
Price was CA $2,956, price is now CA $2,581 per person
CA $2,581
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to West End (CYB)
9.4/10 Exceptional! (16 reviews)
The room and amenities were spotless. The food was excellent as well as the service. Beautiful and quiet

Reviewed on Feb 16, 2026

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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 $565 per night from Jun 21 to Jun 22
CA $565
CA $777 total
Jun 21 - Jun 22
includes taxes & fees
9.4/10 Exceptional! (16 reviews)
"Awesome 👍"

Reviewed on Feb 24, 2026

Le Soleil d'Or CaymanBrac
Snorkelers & Divers Paradise-Cayman Brac-2 Bedroom On Beach With Deck

Snorkelers & Divers Paradise-Cayman Brac-2 Bedroom On Beach With Deck

Cayman Brac
10/10 Exceptional! (65 reviews)
"Best getaway of my life. The snorkeling out front (and half a mile up the road) was amazing! Beautiful space, great neighbors. Amazing A/C and comfy beds."

Reviewed on Apr 24, 2026

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Snorkelers & Divers Paradise-Cayman Brac-2 Bedroom On Beach With Deck
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!
See all 81 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.
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Stay near popular South Side attractions

Cayman Brac Lighthouse

8.8/5 (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

Can I cancel my flight booking to South Side due to COVID-19?
Our helpful Customer Service Portal is your one-stop shop for almost every travel question, including about flight cancellations and changes due to COVID-19. For greater peace of mind, we recommend looking over the terms and conditions of your chosen airline before booking a seat.
What's the best way to find cheap flights to South Side that have flexible change policies?
When it comes to traveling these days, flexibility is key. That's why we've added a "No change fee" filter to help you locate flexible, affordable fares to South Side. It's on the left of your screen right underneath the "Flexible change policies" heading.
What are some of the general tips for travelers to South Side during the COVID-19 outbreak?
COVID-19 has brought about significant changes to the way we travel. If you're planning a vacation in South Side, these tips will help you navigate these new rules and challenges:
  • Know what rules and restrictions apply to both your origin and destination. You may not be able to travel depending on local circumstances, so remember to check government advisories before booking.
  • When you go through airport checkpoints, do not remove your face mask. You will be required to lower it briefly to confirm your identity. Travelers who refuse to wear a face mask may face civil penalties and may also be escorted from the building.
  • Avoid handing your boarding pass (electronic or paper) directly to a TSA employee. Instead, place your pass on the reader and then hold it up so the agent can inspect it.
  • You are now allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on bag. This will need to be removed for X-ray scanning.
  • Put any personal items (like your phone and wallet) in your carry-on instead of a bin to reduce handling during screening.
  • Separate any food you have for X-ray screening. Putting it in a clear plastic bag and into a bin reduces the need for a TSA agent to handle and inspect your belongings.

Which airlines fly to South Side?
Cayman Airways runs flights into or near South Side, including 390 that arrive at Owen Roberts Intl. Airport (GCM) each month. Figure out your travel dates and then book your seat early to bag a bargain.
How can I find cheap tickets to South Side?
You'll always pick up an unbeatable deal with Expedia, but our "flexible dates" search function makes it even easier. Enter your preferred flight date, then tick the flexible dates box above to reveal the cheapest prices for nearby days. was the lowest price for a flight to South Side in the last seven days.
How much is a flight to South Side?
One-way flights leaving () sold for as little as in the last seven days. During this time, the price of a return airfare to South Side varied between and . If you spot a bargain, grab it quickly — these fares don't hang about.
What are the most popular airports to fly into in South Side?
The principal gateway to South Side, around 408 flights cruise into Owen Roberts Intl. Airport (GCM) every month. Find an amazing deal, lock in your fare and get ready to discover this popular region.
When is the cheapest time to fly to South Side?
Jetting off on a Tuesday, followed by a Monday, is usually the best way to pick up the cheapest fare. Stay away from the weekends if you can, because Saturday is typically the costliest day. Spend the funds you saved enjoying yourself in South Side instead!
How much is a plane ticket to South Side?
In the last seven days, plane tickets ranged between and . Swipe through our fabulous deals to South Side, pick your favorite and then start packing your suitcase.
Which airlines with flights to South Side employ COVID-19 cleanliness policies?
As restrictions ease and people begin flying again, many airlines have adopted policies such as social distancing to help lessen the spread of COVID-19. Here are a couple of excellent examples:
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.