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!

09/02/2026

The Florida Keys is truly a place unlike anywhere else in the world.

And this island paradise is waiting for YOU.

Get ready for a trip filled with sunshine, saltwater, and a never ending feeling of serenity.

🎥 Some clips courtesy of Key West Locals

08/31/2026

Because life is better when you take a moment to slow things down.

One of the best places to experience a slower pace?
Islamorada, Florida.

Come experience the true definition of island life by booking your rental with us here at Freewheeler Vacations.

Giving a whole new meaning to freshly caught. Be sure to add Bad Boy Sushi to your upcoming vacation itinerary and get r...
08/28/2026

Giving a whole new meaning to freshly caught.

Be sure to add Bad Boy Sushi to your upcoming vacation itinerary and get ready for sushi unlike anything you’ve ever had before!

We promise this is a spot you DON'T want to miss!

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.

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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