Title: South Side Vacation Rentals : Search Short-Term Rentals | Expedia.com

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

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## Check prices for these dates

In two weeks

[Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=553248635975749438&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=553248635975749438&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=553248635975749438&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=553248635975749438&startDate=2026-06-05&endDate=2026-06-07&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.com/Hotel-Search?destination=South+Side%2C+Cayman+Islands&regionId=553248635975749438&latLong=19.713796%2C-79.798143&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=VILLA)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=South+Side%2C+Cayman+Islands&regionId=553248635975749438&latLong=19.713796%2C-79.798143&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=APARTMENT)

Condos

[](https://www.expedia.com/Hotel-Search?destination=South+Side%2C+Cayman+Islands&regionId=553248635975749438&latLong=19.713796%2C-79.798143&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=CONDO)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=South+Side%2C+Cayman+Islands&regionId=553248635975749438&latLong=19.713796%2C-79.798143&adults=2&startDate=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&lodging=VACATION_HOME)

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## Top South Side Hotel Reviews

![Luxury Oceanfront Villa, 2 Primary Suites + 3rd bdrm, Pool ](https://images.trvl-media.com/lodging/45000000/44070000/44065300/44065259/471436e6_y.jpg)

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

10/10 Excellent

"This was our third visit to Stake Bay and we are planning another return for next year. We truly love Cayman Brac and feel blessed we found the most beautiful and perfect home for us. Thank you from your very happy Alaska guests."

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

![Only steps to the beach](https://images.trvl-media.com/lodging/102000000/101450000/101445200/101445153/7c9c7aac_y.jpg)

### Only steps to the beach

10/10 Excellent

"Great location and super clean. Would stay here again."

[](https://expedia.com/Bouvet-Island-Hotels-Only-Steps-To-The-Beach.h101445153.Hotel-Information)

![Snorkelers & Divers Paradise-Cayman Brac-2 Bedroom On Beach With Deck ](https://images.trvl-media.com/lodging/33000000/32170000/32168400/32168337/de346a61_y.jpg)

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

10/10 Excellent

"Lovely location, fantastic views and friendly community! Snorkel right from the shore, watch the sunset and walk to the pub. Host was responsive and helpful. "

[](https://expedia.com/West-End-Hotels-Snorkelers-Divers-Paradise-Cayman-Brac-2-Bedroom-On-Beach-With-Deck.h32168337.Hotel-Information)

![Incredible Views, Waterfront Luxury Private Villa with Central AC](https://images.trvl-media.com/lodging/32000000/31730000/31721600/31721553/5fefea2b_y.jpg)

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

10/10 Excellent

"The place was amazing and everything was very well taking care of. I would highly recommend this place."

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

![Private 2-b beachfront cottage w/ hammocks, screened-in veranda, sunsets & more!](https://images.trvl-media.com/lodging/34000000/33490000/33486700/33486647/58b05173_y.jpg)

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

10/10 Excellent

"Place is super clean, location was perfect. Peaceful and very relaxing. Gorgeous sunsets. We definitely want to come back. "

[](https://expedia.com/West-End-Hotels-Sunsets.h33486647.Hotel-Information)

![Serenity On The Bay2 - Two Bed Apt Close to Supermarkets, Shops and Restaurants!](https://images.trvl-media.com/lodging/45000000/44680000/44670500/44670448/17f65372_y.jpg)

### Serenity On The Bay2 - Two Bed Apt Close to Supermarkets, Shops and Restaurants!

10/10 Excellent

"Host was very helpful arranging taxis, great, private spot. Great snorkeling right out front of the house. Hermit crabs everywhere. Not a soul on the beach, no noise from neighbors. This is the perfect spot if you’re looking for solitude (which I usually am). You definitely want to rent a car. There are only 2 taxis on the island, and the shoulders on the road aren’t ideal for walking. "

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

![PLEASE COME AND RELAX ON OUR PRIVATE BEACH!](https://images.trvl-media.com/lodging/34000000/33740000/33736200/33736125/7ac30eff_y.jpg)

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

10/10 Excellent

"A great weekend get away"

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

![Lovely 'Sea Dreams Villa' w/ Private Beach & Deck!](https://images.trvl-media.com/lodging/22000000/21670000/21661100/21661097/e0673ed7_y.jpg)

### Lovely 'Sea Dreams Villa' w/ Private Beach & Deck!

10/10 Excellent

"Very intriguing location…"

[](https://expedia.com/West-End-Hotels-Lovely-Sea-Dreams-Villa-W-Private-Beach-Deck.h21661097.Hotel-Information)

![Serenity On The Bay1 - One Bed Apt Close to Supermarkets, Shops and Restaurants!](https://images.trvl-media.com/lodging/89000000/88650000/88646400/88646355/c0f71325_y.jpg)

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

10/10 Excellent

"The house was cleaning and match exactly as announced."

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

## 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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