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!

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.

We like to think that we are the BEST and now is your chance to show us that we are. This is FINAL WEEK of voting for Be...
09/28/2026

We like to think that we are the BEST and now is your chance to show us that we are.

This is FINAL WEEK of voting for Best Of The Upper Keys and we need YOUR HELP.

Whether you have rented a vacation home with us once or we are a staple in your annual trip down to the Florida Keys, we would love it if you could vote for us for "Best Vacation Rental Company" and help us continue to showcase this beautiful island that we call home.

Votes can be given DAILY at keysweekly.com/buk26 through Sunday, October 4th and the more we get, the better chance we have at making it to the Top 3!

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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