Freewheeler Vacations

For more than 35 years, Freewheeler Vacations has been welcoming guests to the sun-soaked shores of the Upper Keys. Locally owned and deeply rooted in the island community, we specialize in tropical escapes—from waterfront estates and coastal retreats to cozy condos and pet-friendly getaways. Our team combines island hospitality with trusted property management expertise to ensure every stay feels easy, memorable, and distinctly “Keys.” Whether you're here to unwind, explore, or soak in the coastal beauty, Freewheeler Vacations helps you experience the Keys the way it was meant to be enjoyed.