Freewheeler Vacation Rentals

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Freewheeler Vacation Rentals 🏖️ Voted #1 Vacation Rental Company-Upper Keys
☀️ Supporting guests & hosts for 30+ years
🌊 Click the link below for our free Keys Area Guide
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Freewheeler Vacations has been offering vacation rental homes and condos on the Upper Keys for more than 25 years. Our vacation properties, available for a week or longer, have all the amenities of home. Just bring your toothbrush & bathing suit!

We did it again... and by we... we mean YOU! We have officially made it to the Top 3 for the 2026 Best Of The Upper Keys...
10/19/2026

We did it again... and by we... we mean YOU!

We have officially made it to the Top 3 for the 2026 Best Of The Upper Keys Nominations for "Best Vacation Rental Company" and we are so honored to have your support. As a locally owned and operated business we love getting to share our slice of paradise with all who visit and this nomination will only help us continue to do so.

Ready to make it so we turn that 3 into a 1? Vote for us DAILY at keysweekly.com/buk26/ and let's show everyone who the BEST of the Upper Keys is.

10/16/2026

The cure for anything is always... saltwater.

So come take a dip down here in the beautiful Florida Keys.

Ready to wake up with sunshine, saltwater, and sand between your toes?Trade your sweater in for a swimsuit and come star...
10/14/2026

Ready to wake up with sunshine, saltwater, and sand between your toes?

Trade your sweater in for a swimsuit and come start your morning in Islamorada!

Book your Florida Keys vacation rental at freewheelervacations.com

10/12/2026

Your PERFECT Florida Keys escape is waiting.

Let us help you find your dream vacation rental!

For nearly 40 years, we have been a trusted local company offering curated homes, local knowledge, and personalized hospitality to make your Florida Keys vacation truly unforgettable.

Whether you’re visiting with friends, family, your partner, or even just yourself... we have got just the home for YOU!

10/09/2026

The experiences you make time for today will soon become the stories you tell for the rest of your life.

Let’s face it... work will always be there but the chance to travel the world will not.

The first place to add to your list? The Florida Keys!

With an island lifestyle you will never forget, it is safe to say that Islamorada will hold a special place in your memory from the moment you first step foot into this tropical paradise.

Some invitations simply cannot be refused. So stop whatever you are doing and book that trip to the Florida Keys TODAY.
10/07/2026

Some invitations simply cannot be refused.

So stop whatever you are doing and book that trip to the Florida Keys TODAY.

Address

Islamorada, FL
33036

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm

Telephone

+13056642075

Website

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