859+ Cypress Island Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Cypress Island

Discover more than 859 StayAndPlay accommodations in Cypress Island, perfect for your golf getaway. StayAndPlay offers luxury golf resorts, private villas, and vacation rentals with everything you need for a relaxing escape near Cypress Island, FL.

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 Cypress Island? 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 Cypress Island pet-friendly golf accommodations and easily book your dream golf resort or villa rental in Cypress Island with StayAndPlay.

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Frequently Asked Questions About Cypress Island Holiday Rentals

There are a lot of options in Cypress Island. If you plan on staying in the Cypress Island 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 Cypress Island:

There are many holiday rentals available in Cypress Island; however, here are a few of the most popular holiday homes listed in Cypress Island on our website:
At StayAndPlay most of our places to stay are perfect for families. Check out the complete list of holiday homes in Cypress Island to find one that works for you.
Yes, there are 859 self-catering family homes and holiday rentals in Cypress Island.
There are more than 859 luxury holiday homes in or near Cypress Island, according to 2025 data from StayAndPlay. Consider these homes for your next holiday:
Yes, there are 859 pet friendly rentals that are available in Cypress Island.