1. Cayman Islands
  2. South Side
  3. Holiday Homes

26+ South Side Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near South Side

Discover more than 26 StayAndPlay accommodations in South Side, perfect for your golf getaway. StayAndPlay offers luxury golf resorts, private villas, and vacation rentals with everything you need for a relaxing escape near South Side, .

Whether you're seeking upscale golf-front resorts, private luxury villas, spacious vacation homes, or family-friendly golf retreats, we can help you find the ideal stay. Our rentals feature top-tier amenities such as private pools, fully equipped kitchens, outdoor patios, hot tubs, and Wi-Fi, ensuring your group enjoys a comfortable and memorable stay.

Planning a group golf trip to South Side? StayAndPlay guarantees a unique and unforgettable experience with plenty of options for families, large groups, or private rentals for long or short stays. Explore our South Side pet-friendly golf accommodations and easily book your dream golf resort or villa rental in South Side with StayAndPlay.

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Frequently Asked Questions About South Side Holiday Rentals

There are a lot of options in South Side. If you plan on staying in the South Side area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in South Side:

There are many holiday rentals available in South Side; however, here are a few of the most popular holiday homes listed in South Side on our website:
At StayAndPlay most of our places to stay are perfect for families. Check out the complete list of holiday homes in South Side to find one that works for you.
Yes, there are 26 self-catering family homes and holiday rentals in South Side.
There are more than 26 luxury holiday homes in or near South Side, according to 2025 data from StayAndPlay. Consider these homes for your next holiday:
Yes, there are 26 pet friendly rentals that are available in South Side.