South Side Holidays from £597

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Your South Side Holiday

Say yes to new adventures with a customised South Side holiday package. Make sure you visit East End, where its unique character, charm and coastal beaches are guaranteed to be among the best parts of your break. Start your trip to South Side by spending a few days in East End, one of the best cities here. From the moment you book your South Side holiday to when you return home, Expedia will be with you each step of the way.

Top South Side Flight + Hotel Deals

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

Conch Club Cottage

2 out of 5
Price was £802, price is now £597 per person
£597
per person
9 Aug - 12 Aug
found 10 hours ago
Return flight included
Miami (MIA) 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 4 Nov 2025

Le Soleil d'Or CaymanBrac

Le Soleil d'Or CaymanBrac

3.5 out of 5
Price was £875, price is now £682 per person
£682
per person
9 Aug - 12 Aug
found 10 hours ago
Return flight included
Miami (MIA) 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 16 Feb 2026

South Side Essential Information

Language
English
Closest Airport
Owen Roberts Intl. Airport (GCM)

Top hotels in South Side

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 £407 per night from 2 Jun to 3 Jun
£407
2 Jun - 3 Jun
includes taxes & fees
9.4/10 Exceptional! (16 reviews)
"Awesome 👍"

Reviewed on 24 Feb 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 24 Apr 2026

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Snorkelers & Divers Paradise-Cayman Brac-2 Bedroom On Beach With Deck
Ocean view from every room ,quiet neighborhood family friendly.Bluff view

Ocean view from every room ,quiet neighborhood family friendly.Bluff view

Cayman Brac Sister Islands
6/10 (2 reviews)
"Condo was rundown and not very clean - it reeked (possibly due to unresolved water leaks?), only one shower had warm water, the freezer couldn’t be opened, the fridge sounded like it was about to blow, etc. Dishes had to be washed Before use, kitchen floor had sticky patches (?). Not great for families ..."

Reviewed on 3 Feb 2026

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Ocean view from every room ,quiet neighborhood family friendly.Bluff view
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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

West End Point Outlook

You can learn about the history of West End with a visit to West End Point Outlook. Amble around this relaxing area's beaches or seek out the snorkelling spots.

West End Point Outlook

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 travelling 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 travellers 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 holiday 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. Travellers 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 favourite 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. Flight-inclusive packages are ATOL protected.