Your Florida Keys Getaway Starts Here

Explore the Florida Keys with Freewheeler Vacations, the largest and longest-established vacation rental company in the Upper Keys. For over 35 years, the same ownership and management team has been providing first-class service to both guests and property owners, delivering trusted local expertise and unforgettable island stays.

Vacation Better with Freewheeler

Freewheeler Vacations proudly offers a diverse collection of homes throughout the Upper and Middle Keys, ranging from luxury waterfront estates to charming one-bedroom condos. No matter the size of your group or your budget, we have a home that fits your needs. Backed by 35 years of local expertise, our team is dedicated to helping every guest experience the Florida Keys in a way that feels relaxed, memorable, and uniquely their own.

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!