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!

10/09/2026

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!

The universe has a secret message for you... but only if you zoom in! Let us help you find your perfect island escape. F...
09/23/2026

The universe has a secret message for you... but only if you zoom in!

Let us help you find your perfect island escape. For nearly 40 years, Freewheeler has been a trusted local company offering curated homes, local knowledge, and personalized hospitality to make your Florida Keys vacation unforgettable.

So much to the point that we are the current holders of "Best Vacation Rental Company".

Want to help us keep that title? Vote for us in this year's The Keys Weekly Newspapers Best Of The Upper Keys nominations!

09/22/2026

Sometimes the best plan is having absolutely no plan at all.

And the best place to have no plans is down here in the Florida Keys.

Speaking of the BEST... please vote for us in this year’s Upper Keys Weekly Best Of The Upper Keys nominations for “Best Vacation Rental Company”.

Submit your vote DAILY through Sunday, October. 4th!

09/18/2026

We may not have the answer on how to start a new life in the Florida Keys...

BUT we can definitely help you in making the most of your time here!

With countless rentals available across Islamorada, your personal slice of paradise is just waiting for you. Whether you’re planning a solo adventure, a romantic escape, a family gathering, or anything in between, we’ve got you covered.

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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