Freewheeler Vacation Rentals

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!

08/24/2026

Technically, the answer to every problem is a vacation down here in the Florida Keys.

So stop stressing and start planning your next get away to Islamorada.

Not sure where to start…? Work with us here at Freewheeler Vacations to find the perfect rental for your dream trip.

We’ve got something for everyone!

Sunshine, saltwater, and sand does a body good.And it's even better when all of that is found down here in the Florida K...
08/21/2026

Sunshine, saltwater, and sand does a body good.

And it's even better when all of that is found down here in the Florida Keys.

08/14/2026

Sometimes in life you have to take a risk and listen to your financially irresponsible friend.

And in our case, we can very much say... that risk paid off.

So if you are seeing this, say "YES" the next time your friend asks if you want to go on vacation to the Florida Keys.

The one thing we love more than Islamorada?Getting to share it with each and every one of YOU.Come find out why this mag...
08/12/2026

The one thing we love more than Islamorada?
Getting to share it with each and every one of YOU.

Come find out why this magical slice of paradise holds such a special place in our hearts.

08/10/2026

The summer heat has started to fade but the Florida Keys still remain as vibrant as ever.

This is the perfect time to come explore our stunning coral reefs, indulge in fresh seafood, and soak up the lively atmosphere that makes the Keys so unique.

See you soon?

08/07/2026

No stress.

Just calm seas. Endless sunsets. And salty air.

Only in the Florida Keys.

Labor Day Weekend is right around the corner.Your weekend can AND SHOULD very much look something like this. Because the...
08/05/2026

Labor Day Weekend is right around the corner.

Your weekend can AND SHOULD very much look something like this.

Because there's no better way to celebrate than with a long weekend in Islamorada.

Reach out today and let's turn those plans into a reality.

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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