South Side Vacations from $1,367

Name: Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!
Rating: 10

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The Latest South Side vacation packages

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

Conch Club Cottage

$1,367

per person

Aug 1 - Aug 6

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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

$1,490

per person

Aug 1 - Aug 6

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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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Discover the most popular places to visit in South Side

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.

West End Point Outlook

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

National Trust Parrot Reserve

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.

South Side Hotel Deals

Le Soleil d'Or CaymanBrac

2147 South Side Road West End

Fully refundableReserve now, pay when you stay

$503 nightly

$555 total

May 17 - May 18

Total with taxes and fees

9.4/10 Exceptional! (16 reviews)

Awesome 👍

Reviewed on Feb 24, 2026

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

Cayman Brac Sister Islands

10/10 Exceptional! (9 reviews)

Excellent location, right on the beach, with no neighbours on either side. Very private. Very clean. All appliances, including washer and dryer work well. Plenty of beach towels. Sitting on the deck with the wind blowing through the palm trees couldn’t be more pleasant. Very close (approx. 8 minutes) ...

Reviewed on Apr 2, 2026

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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.