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Top South Side Hotel Reviews

Peaceful Penthouse Getaway with Stunning Views

10/10 Excellent

"Nice clean place to stay by the sea on the Brac. Will definitely return next year."

Le Soleil d'Or CaymanBrac

10/10 Excellent

"From the moment we arrived, this luxury plantation exceeded every expectation. The service was truly five-star, and the staff made us feel like royalty throughout our entire stay. We stayed in the beautiful three-bedroom, three-bathroom home, which was impeccably clean, tastefully decorated, and equipped with every modern amenity we could have needed. It was the perfect place for my husband, our three kids, and me to relax and enjoy quality family time. One of our favorite features was the picturesque staircase leading from the top of the bluff down to the pool and restaurant. The walk was absolutely breathtaking and added to the charm and beauty of the property. The restaurant by the pool was beautiful as well. The ambiance was elegant yet relaxing, the music created the perfect atmosphere, and every meal we ordered was outstanding. The menu offered wonderful choices, and the chefs prepared each dish to perfection. The wait staff was attentive, warm, and genuinely cared about making our experience unforgettable. We also loved the guided golf cart tour of the stunning 20-acre plantation. Learning about the property while taking in the incredible scenery was a highlight of our trip. To top it off, they hand-cut a variety of fresh fruits for us to sample, which was such a thoughtful and memorable touch. Every detail of our stay reflected excellence. The accommodations, the hospitality, the food, the scenery, and the personal touches made this one of the best vacations!"

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

10/10 Excellent

"The property was impeccable in cleanliness. The check in process was very simple and the property manager was present to explain everything. The best part was the fabulous view of the ocean and the reef. We had a resident nurse shark that would come by the shallow reef every afternoon. The pictures on the listing showed exactly how it really was."

Luxury Oceanfront Cayman Brac Escape, Private Pool, 3BR Stunning Caribbean Views

10/10 Excellent

"Tide's End is a very nice house in a beautiful setting. We had a wonderful family vacation here. My daughter and I spent a few days scuba diving with "Reef Divers" while the rest of the family was perfectly content relaxing at the house (usually in the pool) enjoying the fantastic Caribbean views. "Derwin" (the property manager) met us at the airport, escorted us to the property, and made sure we were familiar with all the features of the home before leaving us to settle in. The facility was very clean and well kept, the communication was easy, and the added touch of personally greeting us at the airport was over the top. We have stayed in many VRBOs over the years and never had that experience. We can highly recommend Tide's End."

West End Cayman Brac Ocean front with pool at Carib Sands

10/10 Excellent

"Our stay at Stumble Inn was fantastic! Karen is a great host, very responsive to questions and she was super accommodating when we needed to make date changes. She was helpful with suggestions regarding car rental, dive shops, restaurants and bars. The condo was clean and well-stocked with basics (even king ice in the freezer!). The view from the deck was awesome; a great spot to enjoy your morning coffee or afternoon happy hour!"

Find out more about South Side

Everything you need to know about South Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Side vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Side. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Side rentals

At Expedia, we put the best South Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top South Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Side vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Find vacation rentals that suit your style

Top South Side Hotel Reviews

Peaceful Penthouse Getaway with Stunning Views

Incredible Views, Waterfront Luxury Private Villa with Central AC

Le Soleil d'Or CaymanBrac

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

Luxury Oceanfront Cayman Brac Escape, Private Pool, 3BR Stunning Caribbean Views

Ocean Odyssey 2000 sq ft 3-bdr 2.5-bath Beachfront Home with Stunning Views!

Blossom Village Cottage – Charming Beachfront Cottage by Cayman Villas.

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

West End Cayman Brac Ocean front with pool at Carib Sands

Find out more about South Side

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