South Side Vacation Rentals

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Vacation Rentals in South Side

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

10.0 out of 10, Exceptional, (5)
"Enjoyed our time at the Brac"
Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!

Only steps to the beach

Only steps to the beach

THE ULTIMATE LUXURY BOTANICAL FAMILY ESTATE VERY LARGE 3,480 SQFT ON THE BEACH!!

6.4 out of 10, (5)
"I got an email on the day of our arrival saying that the reservation was canceled to a break in. Had to scramble to find a place for 6 people. We were successful due to the help of some of the locals. During our conversation was told that the house as trashed During a party mor than a week before our arrival, further more they told me that even without the damage done during the party that the house is run down and seriously in need of repairs and should not even be available to rent. Over all...
THE ULTIMATE LUXURY BOTANICAL FAMILY ESTATE VERY LARGE 3,480 SQFT ON THE BEACH!!

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

10.0 out of 10, Exceptional, (55)
"Everything was great with this property! I would highly recommend it!"
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

Villa, Pool, 3 Berms, 2.5 baths, breathtaking views, reef protected area, kayaks

9.8 out of 10, Exceptional, (30)
"This house is in a great location just a few minutes from grocery, restaurants and the dive shops. The outdoor space is fantastic with a warm pool and beautiful ocean views, and the screened porch is nice for enjoying warm evenings without bugs. The inside is dark and has lots of knickknacks, so it’s not a good place for young children."
Villa, Pool, 3 Berms, 2.5 baths, breathtaking views, reef protected area, kayaks

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

9.0 out of 10, Wonderful, (6)
"Everything we needed for a relaxing 3 night stay on Cayman Brac. Beds were very comfortable, good shower, plenty of towels and adequate kitchen facilities. We particularly enjoyed swimming and snorkeling directly from the property. "
Southern Exposure, Secluded New Beach House on Cayman Brac! Divers delight!

The Alexander # 210 - Queen Suite

10.0 out of 10, Exceptional, (1)
"Hotel was nice and very accurate to listing. Location is very convenient to airport, stores, restaurants, and diving. Staff was friendly throughout my stay."
The Alexander # 210 - Queen Suite

The Alexander - #201 2 Bedroom Suite

10.0 out of 10, Exceptional, (2)
"We stayed in the 2 bed/2bath suite which we loved. Although there isn’t much of a common area, we spent all of our time on the balcony overlooking the pool and bar area. We looked at various rentals for next year but decided the hotel was perfect! The entire staff was extraordinarily friendly and helpful. The food—especially breakfast—was great. This is a great place to stay for our yearly dive vacation."
The Alexander - #201 2 Bedroom Suite

Alexander - # 105 Queen Suite

Alexander - # 105 Queen Suite

The Alexander Suites - #103 Queen Suite

8.8 out of 10, Excellent, (3)
"I'd like to see more locals working at the Alexander. The cleaner lady was the friendliest person there, love her. The rooms could use an update in furniture and kitchenware / appliances"
The Alexander Suites - #103 Queen Suite

The Alexander Suites #102 - Double Queen

10.0 out of 10, Exceptional, (1)
"This was the perfect place for our short Cayman Brac trip. Next time we will stay longer. Absolutely no negative comments…highly recommend😃"
The Alexander Suites #102 - Double Queen

Cayman Brac Beach Villas

3.5 star property
Cayman Brac Beach Villas

Kings Point

3.5 star property
9.4 out of 10, Exceptional, (3)
"Kings Point is the best. Spacious clean facility. So peaceful with beautiful view. Has all the comforts of home and excellent internet connection. This will be my choice lodging when I return to Cayman Brac. "
Kings Point

Villa - Beach Front

Villa - Beach Front

King Studio

King Studio

Three-Bedroom Villa

Three-Bedroom Villa

Beach Front Paradise Home. Luxurious Funishings!

10.0 out of 10, Exceptional, (57)
"We had a fantastic visit to Cayman Brac and Paradise Found beach home. During our stay Hurricane Raphael hit the island. Randall and Jeffrey were very helpful with getting us situated before and during the hurricane. We stayed at the house during the storm and the house held up great. The house was very clean and well maintained. The private beach was fantastic. We did not see a single person on the beach the whole week we were there. The pool is fantastic and a nice way to cool off on a...
Beach Front Paradise Home. Luxurious Funishings!

Serenity On The Bay1 - One Bed Apt Close to Supermarkets, Shops and Restaurants!

9.4 out of 10, Exceptional, (14)
"Serenity on the Bay was as it is named, it was a peaceful and beautiful location, the host Margaret was professional and accomadating. I would recomend staying at Serenity for anyone who loves nature want to relax, see beautiful sunsets."
Serenity On The Bay1 - One Bed Apt Close to Supermarkets, Shops and Restaurants!

Pool, 5 bdrm, sandy beach, sunsets, quiet, cabana w/hammocks, bikes, well kept

10.0 out of 10, Exceptional, (73)
"Property was very nice, we didn’t get to do everything because of hurricane but we still loved it. We were keep informed about what was going to happen and what to do. Would stay again"
Pool, 5 bdrm, sandy beach, sunsets, quiet, cabana w/hammocks, bikes, well kept
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.
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Other types of properties in South Side you may be interested in

Le Soleil d'Or CaymanBrac

3.5 star property
9.6 out of 10, Exceptional, (4)
"My wife and I had a great stay here and would recommend it to anyone visiting Cayman Brac. But, I would recommend not staying at the Beach House. We chose it because it is the only room that is beachside. But, It is 2 miles from the main building and sits on-top of a restaurant and bar so anytime someone closes the door, it reverberates throughout the room. Also, you can hear the bar through the walls so it did get loud on Saturday night. But the main building is quiet and beautiful and the...
The price is CA $364
CA $525 total
includes taxes & fees
Dec 10 - Dec 11
Le Soleil d'Or CaymanBrac

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

10.0 out of 10, Exceptional, (5)
"Enjoyed our time at the Brac"
Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!

Only steps to the beach

Only steps to the beach
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.