Title: South Side Vacation Rentals : Short-Term Rentals for 2026 | Expedia.ca

[South Side Travel Guide](https://expedia.ca/South-Side.dx553248635975749438)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d553248635975749438.Travel-Guide-Hotels)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635975749438.Travel-Guide-Flights)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635975749438.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d553248635975749438.Destination-Travel-Guides)

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635975749438&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=553248635975749438&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975749438&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975749438&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Find vacation rentals that suit your style

Villas

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Cayman+Islands&regionId=553248635975749438&latLong=19.713796%2C-79.798143&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=VILLA)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Cayman+Islands&regionId=553248635975749438&latLong=19.713796%2C-79.798143&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=APARTMENT)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Cayman+Islands&regionId=553248635975749438&latLong=19.713796%2C-79.798143&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=VACATION_HOME)

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## Top South Side Hotel Reviews

![Luxury Beachfront House on Cayman Brac's Nicest Beach! Vacation your way!](https://images.trvl-media.com/lodging/45000000/44230000/44230000/44229946/68e256cb_y.jpg)

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

10/10 Excellent

"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) to dive operations and West End stores and restaurants."

[](https://expedia.ca/West-End-Hotels-Luxury-Beachfront-House-On-Cayman-Bracs-Nicest-Beach-Vacation-Your-Way.h44229946.Hotel-Information)

![RazorBrac SeaEsta - Private Beachfront Home](https://images.trvl-media.com/lodging/36000000/35060000/35055600/35055567/f52357f3_y.jpg)

### RazorBrac SeaEsta - Private Beachfront Home

10/10 Excellent

"My wife and I were very happy with our decision to visit Cayman Brac and stay at RazorBrac SeaEsta. The home sits right at the water’s edge with unobstructed views, and the accommodations were exactly what we were hoping for—comfortable, well-appointed, and relaxing. Highly recommended."

[](https://expedia.ca/West-End-Hotels-RazorBrac-SeaEsta-Private-Beachfront-Home.h35055567.Hotel-Information)

![Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool ](https://images.trvl-media.com/lodging/45000000/44070000/44065300/44065259/166ef87d_y.jpg)

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

10/10 Excellent

"This home is well-taken care of, well-loved and gorgeous. The property manager is lovely to deal with and receptive to all questions; we used him, as we had done before, for a half day boat trip that was exceptional to Bloody Bay Wall and Little Cayman. No complaints. "

[](https://expedia.ca/West-End-Hotels-Luxury-Oceanfront-Villa.h44065259.Hotel-Information)

![Serenity On The Bay2 - Two Bed Airport Supermarkets Shops and Restaurants Close!](https://images.trvl-media.com/lodging/45000000/44680000/44670500/44670448/650ce37a_y.jpg)

### Serenity On The Bay2 - Two Bed Airport Supermarkets Shops and Restaurants Close!

10/10 Excellent

"This is a perfect place for a relaxing getaway. It is located on a secluded stretch of beach - we didn't see anyone else out there for the entire stay. We enjoyed snorkeling right off the beach, sitting watch the waves and sunsets, and stargazing at night.We didn't cook, but the kitchen had everything you needed to do that. There was even a gas grill available to use outside.There is a grocery store close by and a few restaurants within a short driving distance.We had an amazing stay."

[](https://expedia.ca/West-End-Hotels-Serenity-On-The-Bay2-Two-Bed-Apt-Close-To-Supermarkets.h44670448.Hotel-Information)

![Serenity On The Bay1 - One Bed Airport Supermarkets Shops and Restaurants Close!](https://images.trvl-media.com/lodging/89000000/88650000/88646400/88646355/d572f7c6_y.jpg)

### Serenity On The Bay1 - One Bed Airport Supermarkets Shops and Restaurants Close!

10/10 Excellent

"Loved our 8th visit to Brac. Staying at Serenity on the Bay was a good place to stay at this end of the island. Loved the convenience to island amenities and some of our favorite snorkeling spots. The snorkeling right off Serenity’s beach is delightful! Bring water shoes. Enjoyed the sunsets and privacy this spot brings. Beach front view is somewhat limited from the side unit but it didn’t diminish our stay at all. Just moved chairs around! Or we went to sit on the beach which was awesome. The home itself was comfy. Had what we needed to comfortably relax after terrific island explorations of 18 days! Margaret and Robin were very responsive to anything we needed during our stay. I’m already missing the simple solitude of Serenity and the island’s vibe. We’ll be back! "

[](https://expedia.ca/West-End-Hotels-Serenity-On-The-Bay1-One-Bed-Apt-Close-To-Supermarkets.h88646355.Hotel-Information)

![Incredible Views, Waterfront Luxury Private Villa with Central AC](https://images.trvl-media.com/lodging/32000000/31730000/31721600/31721553/eec0c2d9_y.jpg)

### Incredible Views, Waterfront Luxury Private Villa with Central AC

10/10 Excellent

"Everything was perfect. Would definitely stay here again if come back to the Brac."

[](https://expedia.ca/Tibbetts-Turn-Hotels-Everything-About-This-Place-Is-First-Class.h31721553.Hotel-Information)

![Le Soleil d'Or CaymanBrac](https://images.trvl-media.com/lodging/75000000/74430000/74421900/74421869/72668cc8_y.jpg)

### Le Soleil d'Or CaymanBrac

10/10 Excellent

"Awesome 👍"

[](https://expedia.ca/George-Town-Hotels-Le-Soleil-DOr-CaymanBrac.h74421869.Hotel-Information)

![PLEASE COME AND RELAX ON OUR PRIVATE BEACH!](https://images.trvl-media.com/lodging/34000000/33740000/33736200/33736125/00655b98_y.jpg)

### PLEASE COME AND RELAX ON OUR PRIVATE BEACH!

10/10 Excellent

"Always a great weekend getaway!"

[](https://expedia.ca/Spot-Bay-Hotels-PLEASE-COME-AND-RELAX-ON-OUR-PRIVATE-BEACH.h33736125.Hotel-Information)

![Blossom Village Cottage – Charming Beachfront Cottage by Cayman Villas.](https://images.trvl-media.com/lodging/22000000/21670000/21660900/21660830/557b209e_y.jpg)

### Blossom Village Cottage – Charming Beachfront Cottage by Cayman Villas.

10/10 Excellent

"The house, the location and all the people were awesome! We had 4 teenagers traveling with us and I cannot tell you how happy everyone was that they had their own little cottage. The water, the property was absolutely amazing! The kitchen was well stocked and everything was spotless. I am a very picky traveler and I cannot say enough good things about this property."

[](https://expedia.ca/Little-Cayman-Hotels-Blossom-Village-Cottage-Charming-Cottage-By-Cayman-Villas.h21660830.Hotel-Information)

## Find out more about South Side

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with South Side. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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