85+ Cypress Head Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Cypress Head

Discover more than 85 StayAndPlay accommodations in Cypress Head, 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 Head, 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 Head? 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 Head pet-friendly golf accommodations and easily book your dream golf resort or villa rental in Cypress Head with StayAndPlay.

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Frequently Asked Questions About Cypress Head Holiday Rentals

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

There are many holiday rentals available in Cypress Head; however, here are a few of the most popular holiday homes listed in Cypress Head 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 Head to find one that works for you.
Yes, there are 85 self-catering family homes and holiday rentals in Cypress Head.
There are more than 85 luxury holiday homes in or near Cypress Head, according to 2025 data from StayAndPlay. Consider these homes for your next holiday:
Yes, there are 85 pet friendly rentals that are available in Cypress Head.