Come Enjoy – Island Life

Explore the Florida Keys with Freewheeler Vacations, the largest and most enduring vacation rental company in the Upper and Middle Keys. For over 30 years the same ownership and management at Freewheeler Vacations have provided first-class service to both guests and property owners in the Florida Keys.

Vacation Better with Freewheeler


Why choose a vacation rental? Vacation rentals often provide more space, privacy and convenience than hotels. They deliver a home away from home experience where the whole family can spend time together.


Our reservationists are experts on all things Florida Keys, and they are exceptionally qualified to find your perfect vacation rental. The rentals we manage range from massive estates to cozy condos and townhomes. No matter your group size and accommodation preferences, we will find the ideal Florida Keys rental for you and your family.


Click the button below to browse our extensive selection of Upper and Middle Keys rentals, and check out our Area Guide to start planning your ultimate Keys vacation today!


Manage Better with Freewheeler


If you're a homeowner searching for the best property management in the Florida Keys, then look no further than Freewheeler Vacations. Click the button below to learn about our unparalleled property management program, and contact us to inquire about joining the Freewheeler Vacations family!