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!

Our island would be nothing without all the dedicated and hard working individuals who are the backbone of every restaur...
09/07/2026

Our island would be nothing without all the dedicated and hard working individuals who are the backbone of every restaurant, hotel, water-sports shop, and other business down here in the Florida Keys.

Today we honor them and thank them for all they do to make paradise a reality!

Happy Labor Day from us here at Freewheeler Vacations.

Let's keep this short and simple...There is not a singular problem in life that cannot be fixed with a trip to the Flori...
09/04/2026

Let's keep this short and simple...

There is not a singular problem in life that cannot be fixed with a trip to the Florida Keys.

So stop stressing, start planing, and watch all your worries fade away.

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.

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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