South Side Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top South Side vacation package deals
Price found within the past 48 hours. Click for updated prices.
2.0-star property
Conch Club Cottage
10/10 Exceptional! (7 reviews)
Dec 16 - Dec 23
7 night stay
New York (JFK) to Little Cayman (LYB)
American Airlines • Non-stop roundtrip • Coach
Price was $2,080, price is now $1,395 per person
$1,395
per person
found 1 day ago
Very nice, recently remodeled, bright and clean.
Reviewed on Apr 7, 2026
3.5-star property
Le Soleil d'Or CaymanBrac
9.2/10 Wonderful! (20 reviews)
Nov 26 - Nov 30
4 night stay
Chicago (CHI) to West End (CYB)
American Airlines • Non-stop • Coach
West End (CYB) to Chicago (CHI)
Southwest Airlines • Non-stop • Coach
Price was $1,672, price is now $1,440 per person
$1,440
per person
found 1 day ago
Top rated hotels for your South Side vacation package
Le Soleil d'Or CaymanBrac
2147 South Side Road West End
Free Cancellation
Reserve now, pay when you stay
1.03 mi from city center
$462 nightly
The price is $515 total per night
$515 total
Oct 7 - Oct 8
Total with taxes and fees
At Le Soleil d'Or CaymanBrac, guests enjoy features like an outdoor pool, a gym, and free WiFi in public areas. Free parking is available if you drive. Front-desk staff can assist with securing valuables, concierge services, and luggage storage. Additional amenities include coffee/tea in a common area, free use of bicycles, and laundry facilities.
Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!
Cayman Brac Sister Islands
1.29 mi from city center
At this vacation home, guests have access to features like laundry facilities. Transportation is made easy with limo/town car service. Staff members can answer questions about accommodations, and also provide concierge services. This beach vacation home also has barbecue grills.
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.
