Deals on vacations and trips to South Side

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South Side flight + hotel vacation packages

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

Conch Club Cottage

3 out of 5
Price was $1,458, price is now $1,344 per person
$1,344
per person
Oct 10 - Oct 15
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Little Cayman (LYB)
A private beach, 2 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining and relax with free beach cabanas and sun loungers. Families will appreciate the onsite laundry facilities and in-room childcare.
Le Soleil d'Or CaymanBrac

Le Soleil d'Or CaymanBrac

3.5 out of 5
Price was $1,977, price is now $1,834 per person
$1,834
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to West End (CYB)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A coffee shop, a garden, and luggage storage are also on offer.

Top South Side hotels deals

Le Soleil d'Or CaymanBrac

Le Soleil d'Or CaymanBrac

3.5 out of 5
2147 South Side Road, West End
$446 nightly
The price is $492 total per night
$492 total
Oct 1 - Oct 2
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A coffee shop, a garden, and luggage storage are also on offer.
Pool
Breakfast included
Southern Exposure, Secluded New Beach House on Cayman Brac! Divers delight!

Southern Exposure, Secluded New Beach House on Cayman Brac! Divers delight!

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This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Only steps to the beach

Only steps to the beach

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This condo features laundry facilities.
Kitchen
Washer
The Alexander Suites #101 - Queen Suite

The Alexander Suites #101 - Queen Suite

$245 nightly
The price is $268 total per night
$268 total
Sep 8 - Sep 9
Total with taxes and fees
An outdoor pool is available at this aparthotel.
Pool
Kitchen
Stunning and unique 3-bdr oceanfront villa, pool with pergola, hammocks, kayaks!

Stunning and unique 3-bdr oceanfront villa, pool with pergola, hammocks, kayaks!

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An outdoor pool is featured at this villa, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Kitchen
Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!

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

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This vacation home features limo/town car service, laundry facilities, and concierge services. Barbecue grills are provided for your convenience.
Kitchen
Washer
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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.

Popular places to visit

Cayman Brac Lighthouse

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.

Cayman Brac Lighthouse

Bat Cave

3.5/5(2 reviews)

Commune with nature and explore the great outdoors at Bat Cave during your travels in West End. Amble around this relaxing area's beaches, or seek out the snorkeling spots.

Bat Cave

National Trust Parrot Reserve

4.5/5(3 reviews)

Explore the great outdoors at National Trust Parrot Reserve, a lovely green space in East End. Stroll along the beaches or seek out the snorkeling spots.

National Trust Parrot Reserve

Frequently asked questions

How much are vacation packages to South Side?
Starting from as little as $1,344, hotel and flight packages are an ideal way to stretch your vacation budget. Get ready South Side — here you come!
Where can I get the best vacation package deals for South Side?
There are exciting South Side package deals to be scored with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties across the globe? Keep that in mind the next time you're ready to cross another destination off the old bucket list.
Why should I purchase my South Side vacation package via Travelocity?
Because we believe in creating stress-free travel experiences. From flights and hotels to car rentals and activities, our packages make it a breeze to save. Our customer support is available 24/7 to ensure your needs are taken care of. We also have an amazing Price Match Guarantee, so you can lock in your trip knowing you've landed the best deal possible. If you find a lower price, we'll match it!
Can I save money on my South Side car rental if I bundle it with my hotel or flight?
Absolutely. And our South Side vacation packages will help you do it. With only a few clicks you can save money and time by booking everything in one place. Pick up the keys to your rental car and feel the freedom of the open road. Searching for things to do? Add a few tours to your package and make savings on those too.
Which airport is best for South Side?
Gerrard Smith Intl. Airport (CYB) is where many people start their adventures in South Side. Edward Bodden Airfield Airport (LYB) is another option to check out.
What is there to do in South Side?
A visit to South Side won't be complete without venturing out to see Cayman Brac Beaches. Ensure this big-name attraction is at the top of your travel schedule.

Photos of local treasures

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