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!

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

05/22/2026

Islamorada... the place that makes you want to set your status to OOO for the rest of your life.

05/21/2026

Unsure of what to do next during your time in the Florida Keys?
Let the universe choose for you.

Check the number below to see what you're about to add to your Islamorada itinerary.

🌴 7 - Book a snorkel tour and visit the marine life found on Alligator reef.
🌴 16 - Snag sunset cocktails at one of Islamorada's iconic waterfront restaurants.
🌴 29 - Go shopping for a new outfit for the perfect Instagram vacation post.
🌴 31 - Hop on a rental kayak (or paddle board) and see if you can find a manatee
🌴 45 - Relax in a hammock under the sun for some much needed rest & relaxation

Who else can relate?That feeling when the trip is officially booked and suddenly life feels just a little bit lighter. A...
05/20/2026

Who else can relate?

That feeling when the trip is officially booked and suddenly life feels just a little bit lighter. And here at Freewheeler Vacations, we believe where you stay should feel like more than just a rental property.

It should feel like home.

05/18/2026

Calling all ocean lovers!
We've got the PERFECT opportunity for you to get out on the water.

Salty Sailor Island Tours is currently offering $50 off their excursions for any Freewheeler guests!

Call or text 443-718-1702 to book your charter today and experience the BEST part of Islamorada.

05/15/2026

Send this to the person you want to spend all summer going on side quests with 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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