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Top Holiday Rentals in South Side

Our top choices for South Side holiday rentals

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

10.0 out of 10, Exceptional, (58)
"Lovely place very friendly people completely enjoy my stay"
Snorkelers & Divers Paradise-Cayman Brac-2 Bedroom On Beach With Deck

The Alexander Suites #101 - Queen Suite

9.4 out of 10, Exceptional, (6)
"It is so accessible to the airport and other establishments like shops and grocery store."
The price is £209
includes taxes & fees
6 Sept - 7 Sept
The Alexander Suites #101 - Queen Suite

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

9.8 out of 10, Exceptional, (33)
"Five of us enjoyed a beautiful, relaxing stay at Henry's gorgeous home on the South West corner of the island. A spacious house with lots of room for 5 adults, a kitchen with everything that you need to enjoy an easy start to the day or a scrumptious meal at night. The highlights of the property include the pool, many loungers facing the ocean, shaded gazebo and screened in porch. We spent most of our time outdoors, in the porch or enjoying the breeze and sunshine under the sun shades. The...
Stunning and unique 3-bdr oceanfront villa, pool with pergola, hammocks, kayaks!

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

10.0 out of 10, Exceptional, (7)
"Property was great."
Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!

Only steps to the beach

10.0 out of 10, Exceptional, (1)
"The unit had everything we needed for the two of us. Quiet location with beach access. "
Only steps to the beach

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

9.2 out of 10, Wonderful, (7)
"The ocean view and the sun rise was amazing "
Southern Exposure, Secluded New Beach House on Cayman Brac! Divers delight!

Ocean view from every room ,quiet neighborhood family friendly.Bluff view

6.0 out of 10, (1)
"Stay was 1 week and the pool could not be used due to bees and was not cleaned regularly. One bath was out of service because of leak. The place is very nice tho hopefully all issues are fix would stay again."
Ocean view from every room ,quiet neighborhood family friendly.Bluff view

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

6.4 out of 10, (5)
"My family and close friends have traveled to Cayman Brac almost every year now for the last 32 years for our scuba trips and to relax in one of the best islands in the world. This island is a hidden paradise more people should know about but I am happy they do not. I think we have stayed at pretty much every home rental that Cayman Brac has to offer and it is a hit or miss to be honest not everyone is honest about their rentals and be careful with viewing photo shopped rentals! However, this...
THE ULTIMATE LUXURY BOTANICAL FAMILY ESTATE VERY LARGE 3,480 SQFT ON THE BEACH!!

The Alexander # 210 - Queen Suite

9.4 out of 10, Exceptional, (3)
"Great restaurant and bar on site. Staff are superb. The best place to stay on Cayman Brac!"
The price is £212
includes taxes & fees
6 Sept - 7 Sept
The Alexander # 210 - Queen Suite

Charming 1-bedroom condo in superb Cayman Brac with pool

Charming 1-bedroom condo in superb Cayman Brac with pool

The Alexander Suites - #103 Queen Suite

8.8 out of 10, Excellent, (3)
"All around great experience with this property. Interior layout of the hotel and grounds was beautiful and well kept. Rooms were upscale, clean and had small kitchenette - really appreciate how they had coffee makers and a fully stocked kitchen with small appliances including dishware, utensils, cups etc... Property was close to airport, ATM (only one on the island) and to town for quick supermarket runs. Couple of restaurants within walking distance and really close to several snorkeling sites...
The price is £201
includes taxes & fees
1 Sept - 2 Sept
The Alexander Suites - #103 Queen Suite

Alexander - # 105 Queen Suite

The price is £209
includes taxes & fees
14 Sept - 15 Sept
Alexander - # 105 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 price is £260
includes taxes & fees
6 Sept - 7 Sept
The Alexander Suites #102 - Double Queen

The Alexander - #201 2 Bedroom Suite

10.0 out of 10, Exceptional, (2)
"Excellent staff, restaurant was nice."
The price is £308
includes taxes & fees
1 Sept - 2 Sept
The Alexander - #201 2 Bedroom Suite

King Studio

King Studio

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

Three-Bedroom Villa

Three-Bedroom Villa

Villa - Beach Front

Villa - Beach Front

Cayman Brac Beach Villas

3.5 star property
Cayman Brac Beach Villas

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

9.4 out of 10, Exceptional, (20)
"this is one of the best properties I have stayed in, Quite, clean safe and close to basic amenities. The property manager is so efficient and she keeps in contact always in case you need something. The property is clean and affordable. I enjoyed my stay here"
Serenity On The Bay1 - One Bed Apt Close to Supermarkets, Shops and Restaurants!
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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Top South Side Hotel Reviews

Find out more about South Side

Find out more about South Side

Everything you need to know about South Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

South Side holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Side holiday rentals we have selected for you start as low as £201 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Side rentals

At Expedia, we put the best South Side holiday 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 holiday.

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.