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!

06/12/2026

Your alarm clock sounds a bitter different down here in the Florida Keys.

Instead of traffic and notifications, it's the sound of gentle wave accompanied with the occasional rooster call, all signs that the island is waking up around you. And honestly... we wouldn't change it for the world.

Have you experienced a wakeup call like this before?

Nothing says summer in the Florida Keys quite like a cold treat on a hot day. Cool off with a scoop from local favorites...
06/11/2026

Nothing says summer in the Florida Keys quite like a cold treat on a hot day.

Cool off with a scoop from local favorites like:
🍦 Mr. C's Homemade Ice Cream
🍦 Keys Chocolates and Ice Cream
🍦 Mrs Gs Ice Cream & cuban
🍦 Lucky Twist
🍦 Charli's Shave Ice

Whether you're craving key lime, chocolate, or a tropical flavor inspired by the Keys, there's no shortage of sweet ways to stay cool in Islamorada.

📸 Lucky Twist

06/09/2026

Because there is quite literally NO. BETTER. FEELING.

Stepping into Islamorada is like stepping into your own slice of paradise?

Ready to experience it yourself? Book your rental with us here at Freewheeler Vacations and immerse yourself in the true definition of island living.

06/05/2026

With World Ocean Day coming up on Monday, we can’t help but reflect on just how much the ocean means to us. 🌊💙

Here in the Florida Keys, life revolves around the water... sunrise boat rides, salty air, coral reefs teaming with life, endless shades of blue, and the peaceful feeling that only the ocean can bring. It gives us adventure, connection, unforgettable memories, and a place to slow down and appreciate the beauty around us.

World Ocean Day is a reminder to celebrate, protect, and care for the waters that give so much to all of us.

So come Monday, take a moment to get outside, dip your toes in the water, watch a sunset, or simply appreciate the magic of Mother Ocean.

06/03/2026

But the best part is... these are all views you can have when you book your vacation rental with us here at Freewheeler.

Those sun-kissed moments paired with palm trees, saltwater, and cocktails await you.

Book your trip to Islamorada TODAY!

Art, music, local flavor, and island vibes… sounds like the perfect Thursday night to us. 🎨🌴🍻The Islamorada Art Walk, ho...
06/01/2026

Art, music, local flavor, and island vibes… sounds like the perfect Thursday night to us. 🎨🌴🍻

The Islamorada Art Walk, hosted by the Morada Way Arts & Cultural District , is a monthly celebration of creativity and community. Attendees can stroll through the a walkable arts district while exploring local galleries, live music, handcrafted goods, delicious eats, and of course… plenty of local craft beer along the way.

Taking place the third Thursday of every month and completely FREE to attend, the Morada Way Art Walk is a must-experience Islamorada tradition. ☀️

📸: Destination Florida Keys & Key West

05/29/2026

Yes... you did in fact just fall in love with 115 Villa Bella.

Located in Islamorada's premier neighborhood of Venetian Shores, this stunning 4-bedroom, 4-bath waterfront rental offers the perfect balance of comfort and coastal style. Inside, you'll find an open-concept layout with a modern kitchen, spacious island, and high-end appliances... ideal for entertaining or family gatherings. The living area opens to beautiful water views, creating a bright and inviting space to relax after a day on the water.

Outside, enjoy a heated pool, outdoor kitchen, two outdoor TVs, dining area, and outdoor shower, all surrounded by lush tropical landscaping. For boaters, the property features concrete dockage on a deep-water canal with quick access to both the Atlantic Ocean and Florida Bay through Snake Creek.

You head over heels yet? Call us today and book this rental for you next vacation.
305.664.2075

05/27/2026

Islamorada is waiting for you.
Book your trip TODAY!

Looking for an experience you’ll be talking about long after your trip to the Keys is over?We know just the place. For j...
05/25/2026

Looking for an experience you’ll be talking about long after your trip to the Keys is over?
We know just the place.

For just a few dollars at Robbie's of Islamorada , you can hand-feed hundreds of massive wild tarpon, some weighing well over 100 pounds, as they leap straight out of the water right in front of you.

Equal parts thrilling, fun, and VERY Florida Keys.

📸: Robbie's of Islamorada

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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