Holiday Homes in South Side

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in South Side

Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool
Relax by the ocean with a swim in the pool, unwind in the hot tub, or grill a meal at the barbecue.

Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool

10.0 out of 10, Exceptional, (60)
"This was our second time staying at Tides End. We just love this house! The view, the pool, the kitchen! Highly recommended!!"
Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool
Beach Front Paradise Home. Luxurious Funishings!
Enjoy a tranquil beachfront setting with a clear ocean view, a central pool surrounded by lush greenery and palm trees.

Beach Front Paradise Home. Luxurious Funishings!

10.0 out of 10, Exceptional, (63)
"We thoroughly enjoyed our 2 week stay at Paradise Found. The home was well equipped, clean and very comfortable. The screened in porch was a plus. We have vacationed on Cayman Brac many times and Paradise Found is now one of our favorites."
Beach Front Paradise Home. Luxurious Funishings!
Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!
Enjoy the serene ocean views from this expansive deck, surrounded by palm trees and white railings.

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!
Featherstone - The Estate
Guests can enjoy a beachside pool and lush surroundings at this tropical resort.

Featherstone - The Estate

Featherstone - The Estate
PLEASE COME AND RELAX ON OUR PRIVATE BEACH!
Relax on the beach with comfortable seating and stunning ocean views.

PLEASE COME AND RELAX ON OUR PRIVATE BEACH!

9.0 out of 10, Wonderful, (15)
"Perfect locatioon for peace and quiet, however it's quite the distance from grocery stores and other points of interest. Definitely booking again next year."
PLEASE COME AND RELAX ON OUR PRIVATE BEACH!
Little Cayman 3 Bedroom Oceanfront Private Villa
Enjoy a tranquil beach experience with access to the ocean via the wooden pier.

Little Cayman 3 Bedroom Oceanfront Private Villa

10.0 out of 10, Exceptional, (18)
"Best place to stay in Little Cayman, my second time here and enjoyed it so much!"
Little Cayman 3 Bedroom Oceanfront Private Villa
Awesome Sea Views! Secluded Beach
Enjoy a serene beach experience with access to the ocean.

Awesome Sea Views! Secluded Beach

10.0 out of 10, Exceptional, (13)
"Tarpon House has as an amazing location and is very well finished. It was extremely relaxing staying there - quiet and calm, with the Milky Way filling the sky every night."
Awesome Sea Views! Secluded Beach
Nature Escape Getaway w/ in-room dining service & amenities/3bdrm 1bth/sleeps 5
Relax by the pool surrounded by lush greenery and palm trees.

Nature Escape Getaway w/ in-room dining service & amenities/3bdrm 1bth/sleeps 5

8.0 out of 10, Very good, (1)
"Greeted by house manager who took us through the basics. Villa was super clean and very cute. Gorgeous outside area"
Nature Escape Getaway w/ in-room dining service & amenities/3bdrm 1bth/sleeps 5
Southern Exposure, Secluded New Beach House on Cayman Brac! Divers delight!
Enjoy the tranquil ocean views from this serene beachside retreat.

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!
Private 2-b beachfront cottage w/ hammocks, screened-in veranda, sunsets & more!
Enjoy a tranquil beach scene with palm trees and ocean views.

Private 2-b beachfront cottage w/ hammocks, screened-in veranda, sunsets & more!

9.8 out of 10, Exceptional, (55)
"Great time. "
Private 2-b beachfront cottage w/ hammocks, screened-in veranda, sunsets & more!
THE ULTIMATE LUXURY BOTANICAL FAMILY ESTATE VERY LARGE 3,480 SQFT ON THE BEACH!!
Enjoy an ocean view from this beachfront property, featuring a thatched-roof structure, pool, and lush garden.

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!!
2-bd sandy beachfront apt w/ pool, cabana, hammocks, sunsets! a tropical dream!
Relax by the ocean-view pool surrounded by palm trees, shaded by a canopy and accessible via a ladder.

2-bd sandy beachfront apt w/ pool, cabana, hammocks, sunsets! a tropical dream!

10.0 out of 10, Exceptional, (62)
"We spent a week in Cayman Brac and enjoyed staying with Henry. He was super responsive and even helped with booking a rental car. We were not able to do any shore diving or kayaking due to the high winds but still enjoyed the ocean front view and reading in the hammock. "
2-bd sandy beachfront apt w/ pool, cabana, hammocks, sunsets! a tropical dream!
1-bdm tropical beach paradise w/ pool, hammocks, cabana, snorkeling, BBQ & more!
Relax by the ocean with a clear view, surrounded by lush palm trees and a shaded pool area.

1-bdm tropical beach paradise w/ pool, hammocks, cabana, snorkeling, BBQ & more!

10.0 out of 10, Exceptional, (14)
"Stayed for 2 weeks -- they responded immediately to our every need. Highly recommend Secluded Sunsets!"
1-bdm tropical beach paradise w/ pool, hammocks, cabana, snorkeling, BBQ & more!
RazorBrac SeaEsta - Private Beachfront Home
Enjoy stunning ocean views from this balcony with two comfortable chairs.

RazorBrac SeaEsta - Private Beachfront Home

10.0 out of 10, Exceptional, (28)
"I've stayed here many times, it's always clean and pleasant."
RazorBrac SeaEsta - Private Beachfront Home
Ocean view from every room ,quiet neighborhood family friendly.Bluff view
Enjoy a serene beach view from this cozy space, featuring a wooden bench and table, with a large barrel at your feet.

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 ROCK HOUSE with Private Beach on Little Cayman
Enjoy breathtaking ocean views from the balcony of this beachfront property, surrounded by lush tropical vegetation.

The ROCK HOUSE with Private Beach on Little Cayman

10.0 out of 10, Exceptional, (2)
"great location store, is bike able distance , shallow water snorkeling in front of house lots of conch, screen porch is outstanding feature . older houses like this one are usually in best locations"
The ROCK HOUSE with Private Beach on Little Cayman
#1 on island, 2-bdm large and cozy, pool, sandy beach w/ cabana, hammocks & more
Enjoy a tranquil beachside retreat with a pool and lounge chair surrounded by palm trees.

#1 on island, 2-bdm large and cozy, pool, sandy beach w/ cabana, hammocks & more

10.0 out of 10, Exceptional, (64)
"Modern house with lots of space. Immaculate property with an amazing ocean view. Highly recommend this rental!"
#1 on island, 2-bdm large and cozy, pool, sandy beach w/ cabana, hammocks & more
Charming 1-bedroom house by the sea in quaint Cayman Brac
Relax by the serene beachfront infinity pool, offering a tranquil view of the sea.

Charming 1-bedroom house by the sea in quaint Cayman Brac

2.0 star property
Charming 1-bedroom house by the sea in quaint Cayman Brac
Featherstone - The Cottage
Relax by the pool surrounded by lush greenery and palm trees, with the beach just steps away.

Featherstone - The Cottage

10.0 out of 10, Exceptional, (2)
Featherstone - The Cottage
Featherstone - Upstairs Beach Front Apartment
Relax by the pool overlooking the ocean and sandy beach.

Featherstone - Upstairs Beach Front Apartment

8.0 out of 10, Very good, (1)
"Staying at a local's place was the right choice rather than a "resort" / hotel. We wanted a place on the water with a balcony where we could cook. There were a few things that we liked / was disappointed in with Featherstone: What we liked: The views were great. We were glad we choose the "top" of the house as downstairs you could hear a lot of noise. We enjoyed the hammocks both on the beach and our private deck. The wifi and laundry options were wonderful to have on site. What we didn't...
Featherstone - Upstairs Beach Front Apartment
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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